Sulfonamide polyenes and methods for their preparation and use

Abstract

The application belongs to the technical field of new material industry of organic compounds, and particularly discloses a sulfonamide polyene compound and a preparation method and application thereof, the method comprises the following steps: sulfonamide, allyl carbonate, tetrakis(triphenylphosphine)palladium and solvent ethyl acetate are mixed, and then stirred at room temperature for 3-6 hours in an air atmosphere. After the reaction is completed, the sulfonamide polyene compound is obtained through post-treatment and purification. The allyl amination reaction of the allyl carbonate is realized by using the allyl amide and the allyl carbonate as raw materials under mild conditions, and the sulfonamide polyene skeleton is efficiently constructed. The method is simple to operate, and strict anhydrous and anaerobic conditions are not required. The product shows good antibacterial and antioxidant activity, and the synthesized compound can also be used as an important organic synthesis intermediate.

Description

Technical Field

[0001] This invention belongs to the field of new organic compound materials technology, and relates to chemical catalytic reactions, specifically to a palladium-catalyzed allyl amination reaction for the synthesis of sulfonamide polyene compounds and their applications. Background Technology

[0002] Sulfonamide alkenyl compounds, especially polyene nitrogen-containing skeletons, have demonstrated significant value in medicinal chemistry and materials science due to their unique electronic structure and reactivity. Polyene alkaloids often exhibit significant biological activity; for example, amphotericin B, as a polyene macrolide antifungal drug, plays an important role in clinical treatment. Meanwhile, conjugated systems containing alkenyl-substituted nitrogen atoms can serve as core structural units for organic optoelectronic materials to regulate the photoelectric properties of molecules. Furthermore, tertiary amine polyolefins have been shown to have various application potentials, such as serving as carbon dioxide capture and conversion reagents, and possessing pH-responsiveness, antibacterial properties, and ion channel functions. Therefore, developing efficient and universal synthetic methods for sulfonamide polyene compounds has always been a research hotspot in the field of organic synthetic chemistry.

[0003] In the traditional route for achieving N-allylation of secondary sulfonamides, allyl chloride, allyl bromide, and allyl alcohol are commonly used as allylation reagents. However, these methods have significant drawbacks: firstly, they all require the addition of a stoichiometric amount of base to promote the reaction; secondly, the reaction is prone to over-allylation, leading to an increase in byproducts and making selectivity control difficult.

[0004] To overcome the aforementioned drawbacks, researchers have focused on developing catalytic allyl amination methods. Although these catalytic methods avoid the use of stoichiometric bases, they still have the following limitations: 1) In addition to metal catalysts, specific additives (such as ligands or co-catalysts) are usually required, increasing system complexity and cost; 2) Reaction times are generally long; 3) Some methods require heating (such as under reflux conditions). This undoubtedly increases operational complexity, places higher demands on equipment, and consumes more energy, thus hindering their practical application in industrial-scale production.

[0005] Palladium-catalyzed reactions are widely used in the construction of C–C and C–X bonds. Allyl carbonates, as ideal allylation precursors, possess both excellent leaving group (carbonate) properties and alkenylation activity. Their unique advantage lies in the fact that the tert-butoxy anion released in situ under palladium catalysis can act as a base, theoretically eliminating the need for additional base addition. Therefore, based on the properties of allyl carbonates, exploring a palladium-catalyzed system with milder conditions (e.g., room temperature), requiring no strict anhydrous or oxygen-free environment, and without the need for external bases and complex additives, to simply and efficiently construct sulfonamide polyene compounds has significant scientific and practical value. Summary of the Invention

[0006] The purpose of this invention is to overcome the shortcomings of existing technologies and provide a palladium-catalyzed allyl amination reaction for the synthesis of sulfonamide polyenes and their applications. This invention proposes a novel palladium-catalyzed allyl amination reaction strategy for the efficient construction of sulfonamide polyenes. This method, conducted at room temperature and in an air atmosphere, uses readily available sulfonamides and allyl carbonates as raw materials to directly construct C–N bonds and olefin skeletons through a one-step coupling, simplifying the synthetic route. The resulting compounds exhibit excellent antioxidant and antibacterial activities. Furthermore, the synthesized sulfonamide polyenes can serve as important organic synthetic intermediates for further derivatization.

[0007] To achieve the above objectives, the present invention adopts the following technical solution: A sulfonamide polyene compound, wherein the structural formula of the sulfonamide polyene compound is shown below: ,in, R 1 for: any of them, R 2 for: any of them, R 3 for: any of them, R 4 for: Any one of them.

[0008] This invention provides a method for preparing the above-mentioned sulfonamide polyene compound, which is prepared by palladium-catalyzed allyl amination reaction, specifically including the following steps: Sulfonamide compound 1, allyl carbonate 2, and palladium catalyst tetra(triphenylphosphine)palladium (Pd(PPh)) were added. 3)4 After mixing with solvent, the mixture was reacted in air at room temperature with stirring for 3-6 h. After the reaction was completed, saturated sodium chloride solution was added first, followed by extraction with dichloromethane. The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) as eluents to obtain sulfonamide polyene compound 3. The synthetic route of the preparation method is shown below: .

[0009] Specifically, the molar ratio of the sulfonamide compound 1 to the allyl carbonate 2 can be 1:2-2.2.

[0010] Specifically, the molar ratio of the sulfonamide compound 1 to tetra(triphenylphosphine)palladium can be 1:0.08-0.15.

[0011] Specifically, the solvent can be ethyl acetate (EtOAc, EA), and 1-2 mL of solvent can be added for every 0.1 mmol of sulfonamide compound 1.

[0012] More preferably, the molar ratio of the sulfonamide compound 1, allyl carbonate 2, and tetrakis(triphenylphosphine)palladium is 1:2:0.1.

[0013] The present invention also provides the application of the above-mentioned sulfonamide polyene compound in the preparation of antibacterial drugs.

[0014] This invention also provides the application of the above-mentioned sulfonamide polyene compounds in the preparation of antioxidant drugs.

[0015] In this invention, sulfonamide compound 1 can be prepared according to the method reported in the literature (Meng, Q.; Meng, Y.; Liu, Q.; Yu, B.; Li, Z.-J.; Li, E.-Q.; Zhang, J. Enantioselective Synthesis of Oxazocines via MQ-PhosEnabled Palladium-Catalyzed Asymmetric Formal [4+4]-Cycloadditions. Adv.Sci., 2024, 11, 2402170.). The structural formula of sulfonamide compound 1 is shown below: .

[0016] In this invention, allyl carbonate compound 2 was prepared according to the method reported in the literature (Corbett, MT; Baucom, K.; Cui, S.; Dornan, PK; Jiao, F.; Han, J.; Langille, NF; Osgood, S.; Parsons, AT; Quasdorf, KW; et al. Development of a Scalable Route to a Complex Cyclobutane Linchpinvia a Diastereoselective CuI-Catalyzed Vinylation of a Cyclobutanyl Aldehyde. Tetrahedron, 2024, 164, 134168.). The structural formula of allyl carbonate compound 2 is shown below: .

[0017] In this invention, the palladium catalyst used is tetrakis(triphenylphosphine)palladium, abbreviated as Pd(PPh3)4, with the following structural formula: .

[0018] Compared with the prior art, the beneficial effects of the present invention are as follows: 1) Mild and Efficient Reaction Conditions: The palladium-catalyzed allyl amination system proposed in this invention is used for the reaction of sulfonamides and alkenyl carbonates, achieving the allyl amination of alkenyl carbonates and facilitating the efficient construction of sulfonamide polyene compounds. Experimental results show that the reaction proceeds under mild conditions: ethyl acetate as solvent, air atmosphere, and room temperature. This method is simple to operate, does not require strictly anhydrous and anaerobic operation, and achieves good yields of the target product, thus demonstrating superior reaction efficiency and operational simplicity.

[0019] 2) Simple synthetic route: This reaction uses sulfonamides and alkenyl carbonates, which are simple in structure and readily available, as starting materials to directly construct sulfonamide polyene skeletons via a one-step coupling method. This greatly simplifies the cumbersome multi-step functional group conversion in traditional synthetic routes and provides a novel and efficient strategy for constructing such skeletons.

[0020] 3) Excellent bioactivity: The compounds prepared in this invention exhibit significant antibacterial and antioxidant activities and can also serve as important intermediates in organic synthesis. In antibacterial tests, the target product showed inhibition rates of over 99.98% against Staphylococcus aureus and Escherichia coli; in antioxidant tests, the compounds achieved a scavenging rate of over 60% against DPPH free radicals, and a scavenging rate against ABTS free radicals that was close to or even exceeded that of the positive control VC.

[0021] 4) Good biocompatibility: Cytotoxicity tests showed that the target compound exhibited excellent safety in the concentration range of 2.5-5 mg / mL and may have a certain effect on promoting cell activity, providing a good safety window for potential drug development.

[0022] 5) Broad application prospects: This method can be used to achieve post-modification of some bioactive molecules, including ibuprofen and oxaprazin modified with azauracil, providing a powerful tool for new drug development. Attached Figure Description

[0023] Figure 1 The graph shows the in vitro inhibition rate of the target products against Staphylococcus aureus in Examples 1-5.

[0024] Figure 2 The graph shows the in vitro inhibition rate of the target products against Escherichia coli in Examples 1-5.

[0025] Figure 3The graph shows the DPPH free radical scavenging rate results of the target products in Examples 1-5.

[0026] Figure 4 The graph shows the scavenging rate results of the target product ABTS free radical in Examples 1-5.

[0027] Figure 5 The graph shows the toxicity test results of the target products in Examples 1-4 on HaCaT cells at a concentration of 2.5 mg / mL.

[0028] Figure 6 This is a graph showing the toxicity test results of the target products in Examples 1-4 on HaCaT cells at a concentration of 5 mg / mL. Detailed Implementation

[0029] To make the objectives, technical solutions, and effects of this invention clearer, the technical solutions of this invention are described in detail below with reference to specific embodiments. It should be understood that the specific embodiments described herein are for illustrative purposes only and are not intended to limit the scope of this invention.

[0030] Unless otherwise specified, the experimental methods used in the following experimental examples are conventional methods; the materials and reagents used are commercially available unless otherwise specified.

[0031] In the following examples, sulfonamide compounds were prepared according to the method reported in the literature (Meng, Q.; Meng, Y.; Liu, Q.; Yu, B.; Li, Z.-J.; Li, E.-Q.; Zhang, J. Enantioselective Synthesis of Oxazocines via MQ-PhosEnabled Palladium-Catalyzed Asymmetric Formal [4+4]-Cycloadditions. Adv.Sci., 2024, 11, 2402170.), and details can be found in the supporting materials of the literature. The specific synthesis method is as follows: 10 mmol of substituted ethyl ketone was dissolved in 20 mL of ethanol, and 12 mL of 10% sodium hydroxide aqueous solution was added under vigorous stirring. After stirring continuously at room temperature for 30 min, 10 mmol of aldehyde substrate was added, and stirring was continued for 2 h. During the process, a large amount of solid precipitate was precipitated. The reaction solution was cooled to 0 °C, and the filtrate was removed by filtration to obtain the solid chalcone intermediate S1. The crude product did not require further purification. Chalcone intermediate S1 (5 mmol), substituted sulfonamide (5 mmol), and triethylamine (10 mmol) were dissolved in 20 mL of dichloromethane, and the system was cooled to 0 °C. Titanium tetrachloride (5 mmol) was measured using a syringe, and the needle was inserted below the liquid surface and slowly added dropwise to the reaction solution. After the addition was complete, the temperature was raised to 40 °C, and the reaction was stirred for 4 h. After the reaction was completed, water was added to quench the reaction, and the organic phase was collected by separation. The aqueous phase was extracted with ethyl acetate (50 mL × 2), and the organic phase was collected. Using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 5:1) as eluents, the organic phase was purified by silica gel column chromatography to obtain sulfonamide compound 1, as shown in the reaction formula below.

[0032] .

[0033] Allyl carbonate compounds were prepared according to the method reported in the literature (Corbett, MT; Baucom, K.; Cui, S.; Dornan, PK; Jiao, F.; Han, J.; Langille, NF; Osgood, S.; Parsons, AT; Quasdorf, KW; et al. Development of a Scalable Route to a Complex Cyclobutane Linchpin via a Diastereoselective CuI-Catalyzed Vinylation of a Cyclobutanyl Aldehyde. Tetrahedron, 2024, 164, 134168.), details of which can be found in the supporting materials of the literature. The specific synthetic method is as follows: at 0 °C, a 1.0 mol / L solution of vinyl magnesium bromide tetrahydrofuran (47.1 mmol) was added dropwise to an aldehyde (47.1 mmol) in anhydrous tetrahydrofuran (250 mL). After the addition was complete, the reaction mixture was stirred at 0 °C for 10 minutes, then heated to room temperature and stirred for another 4 hours. The reaction was quenched by adding 200 mL of saturated ammonium chloride aqueous solution, followed by extraction with diethyl ether (150 mL × 3). The organic phase was collected, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain intermediate S2. Intermediate S2 (20 mmol) was dissolved in dichloromethane, and the system was cooled to 0 °C. 4-Dimethylaminopyridine (2.5 mmol) was added first, followed by ditert-butyl dicarbonate (22 mmol) pre-dissolved in dichloromethane, which was slowly added dropwise to the above reaction mixture. After reacting for 30 min, the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (volume ratio 15:1) as eluents to obtain allyl carbonate compound 2, as shown in the reaction formula below.

[0034] .

[0035] Room temperature refers to 25±5℃.

[0036] Example 1

[0037] The preparation method of sulfonamide polyene compound 3a in this embodiment includes the following steps: .

[0038] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 85% yield. The chromatographic information is as follows.

[0039] 1 H NMR (400 MHz, Chloroform- d ) δ 6.97 (d, J = 15.9 Hz, 1H), 6.44 (d, J =15.8 Hz, 1H), 5.79 (d, J = 15.9 Hz, 1H), 4.46 (dd, J = 14.5, 5.7 Hz, 1H), 3.95(dd, J = 14.3, 8.5 Hz, 1H), 2.39 – 2.59 (m, 4H), 1.74 (q, J = 7.1 Hz, 2H), 1.63 –1.52 (m, J = 4.3 Hz, 3H), 1.46 (m, J = 8.5, 4.3 Hz, 1H). 13 C NMR (101 MHz, CDCl3) δ149.6, 141.4, 137.0, 136.5, 134.0, 132.4, 129.4, 129.0, 128.6, 128.5, 127.8,127.7, 127.6, 127.4, 126.5, 126.3, 124.7, 121.2, 52.0, 32.7, 31.2, 27.9,27.7, 26.4. HRMS (ESI-TOF) m / z [M + K] + calcd for C 30 H 31 NO2SK + 508.1707; found508.1708.

[0040] Example 2

[0041] The preparation method of sulfonamide polyene compound 3b in this embodiment includes the following steps: .

[0042] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 90% yield. The chromatographic information is as follows.

[0043] 1 H NMR (600 MHz, Chloroform- d ) δ 7.90 (d, J = 7.7 Hz, 2H), 7.51 – 7.39(m, 5H), 7.33 – 7.24 (m, 4H), 7.24 – 7.17 (m, 2H), 7.07 – 6.98 (m, 1H), 6.86(d, J = 15.8 Hz, 1H), 6.42 (d, J = 15.7 Hz, 1H), 6.35 (d, J = 15.8 Hz, 1H), 6.33 –6.23 (m, 1H), 4.38 (dd, J = 14.5, 6.0 Hz, 1H), 4.08 (dd, J = 14.5, 8.2 Hz, 1H),2.57 – 2.48 (m, 1H), 2.49 – 2.40 (m, 2H), 2.40 – 2.30 (m, 1H), 1.80 – 1.64(m, 2H), 1.61 – 1.47 (m, 3H), 1.47 – 1.38 (m, 1H). 13C NMR (151 MHz, CDCl3) δ150.5, 141.1, 137.1, 136.5, 134.1, 132.9, 132.5, 129.0, 128.6, 128.5, 128.4,128.0, 127.8, 127.7, 127.4, 126.6, 126.5, 124.5, 124.3, 123.9, 77.3, 52.1,32.6, 31.3, 28.0, 27.7, 26.4. HRMS (ESI-TOF) m / z: [M + Na] + calcd forC 30 H 30 BrNO2SNa + 570.1073; found 570.1064.

[0044] Example 3

[0045] The preparation method of sulfonamide polyene compound 3c in this embodiment includes the following steps: .

[0046] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 79% yield. The chromatographic information is as follows.

[0047] 1 H NMR (600 MHz, Chloroform- d ) δ 7.96 – 7.85 (m, 2H), 7.59 – 7.52 (m,1H), 7.47 (t, J = 7.8 Hz, 2H), 7.29 – 7.25 (m, 4H), 7.26 – 7.16 (m, 3H), 6.98 –6.95 (m, 2H), 6.90 (d, J = 15.9 Hz, 1H), 6.39 (d, J = 15.7 Hz, 1H), 6.30 – 6.20(m, 1H), 5.73 (d,J = 15.9 Hz, 1H), 4.42 – 4.30 (m, 1H), 3.91 (dd, J = 14.5, 8.3Hz, 1H), 2.53 – 2.29 (m, 4H), 1.75 – 1.63 (m, 2H), 1.58 – 1.46 (m, 3H), 1.45– 1.35 (m, 1H). 13 C NMR (151 MHz, CDCl3) δ 150.1, 141.4, 136.5, 135.6, 134.1,132.9, 132.4, 128.9, 128.7, 128.6, 128.2, 127.9, 127.7, 127.6, 127.4, 126.5,124.5, 121.9, 77.1, 52.1, 32.6, 31.2, 27.9, 27.7, 26.4. HRMS (ESI-TOF) m / z:[M + Na] + calcd for C 30 H 30 ClNO2SNa + 526.1578; found 526.1566.

[0048] Example 4

[0049] The preparation method of sulfonamide polyene compound 3d in this embodiment includes the following steps: .

[0050] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 85% yield. The chromatographic information is as follows.

[0051] 1 H NMR (600 MHz, CDCl3) δ 7.84 (d, J = 8.5 Hz, 2H), 7.43 (d, J= 8.6 Hz,2H), 7.31 – 7.25 (m, 2H), 7.26 – 7.21 (m, 4H), 7.20 – 7.17 (m, 2H), 6.92 (d, J = 15.9 Hz, 1H), 6.40 (d, J = 15.7 Hz, 2H), 6.29 – 6.21 (m, 1H), 5.71 (d, J = 15.9Hz, 1H), 4.41 – 4.35 (m, 1H), 3.91 (dd, J = 14.5, 8.5 Hz, 1H), 2.54 – 2.47 (m,1H), 2.47 – 2.33 (m, 3H), 1.73 – 1.65 (m, 2H), 1.57 – 1.48 (m, 3H), 1.45 –1.38 (m, 1H). 13 C NMR (151 MHz, CDCl3) δ 149.8, 140.0, 138.9, 136.8, 136.4,134.3, 129.5, 129.2, 129.1, 128.6, 127.9, 127.6, 127.5, 126.5, 126.3, 124.4,121.1, 52.2, 32.7, 31.2, 27.9, 27.7, 26.4. HRMS (ESI-TOF) m / z: [M + Na] + calcdfor C 30 H 30 ClNO2SNa + 526.1578; found 526.1585.

[0052] Example 5

[0053] The preparation method of sulfonamide polyene compound 3e in this embodiment includes the following steps: .

[0054] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 85% yield. The chromatographic information is as follows.

[0055] 1 H NMR (400 MHz, CDCl3) δ 7.92 (d, J = 7.7 Hz, 2H), 7.58 (t, J = 7.4 Hz, 1H), 7.49 (t, J = 7.6 Hz, 2H), 7.33 – 7.15 (m, 6H), 6.98 – 6.71 (m, 4H), 6.39(d, J = 15.7 Hz, 1H), 6.31 – 6.19 (m, 1H), 5.72 (d, J = 15.9 Hz, 1H), 4.40 (dd, J =14.6, 5.9 Hz, 1H), 3.90 (dd, J = 14.4, 8.3 Hz, 1H), 2.54 – 2.34 (m, 4H), 1.74 –1.64 (m, 2H), 1.53 (d, J = 7.4 Hz, 3H), 1.40 (d, J = 10.9 Hz, 1H). 13 C NMR (101MHz, Chloroform- d ) δ 163.0 (d, J = 244.8 Hz), 150.7, 141.4, 139.5 (d, J = 7.9Hz), 136.5, 134.1, 132.5, 129.9 (d, J = 8.4 Hz), 129.0, 128.6, 128.2 (d, J= 2.1Hz), 127.9, 127.6, 127.5, 126.5, 124.5, 122.6, 122.2 (d, J = 2.7 Hz), 114.1 (d, J = 21.5 Hz), 112.6 (d, J = 21.9 Hz), 52.0, 32.8, 31.2, 27.9, 27.7, 26.3. 19 F NMR (376 MHz, CDCl3) δ -113.57. HRMS (ESI-TOF) m / z: [M + Na] + calcd forC 30 H 30 FNO2SNa + 510.1873; found 510.1882.

[0056] Example 6

[0057] The preparation method of sulfonamide polyene compound 3f in this embodiment includes the following steps: .

[0058] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 76% yield. The chromatographic information is as follows.

[0059] 1 H NMR (400 MHz, Chloroform- d ) δ 7.80 (d, J = 8.0 Hz, 1H), 7.31 – 7.27(m, 2H), 7.26 (s, 1H), 7.23 (d, J = 7.4 Hz, 1H), 7.17 (t, J = 7.2 Hz, 1H), 7.03 (d, J = 7.5 Hz, 1H), 6.90 (d, J= 15.9 Hz, 1H), 6.38 (d, J = 15.8 Hz, 1H), 6.28(dd, J = 8.5, 5.8 Hz, 1H), 5.72 (d, J = 15.9 Hz, 1H), 4.40 (dd, J = 14.5, 5.6 Hz, 1H), 3.87 (dd, J = 14.5, 8.3 Hz, 1H), 2.41 (d, J = 24.0 Hz, 7H), 1.71 (d, J = 6.3Hz, 1H), 1.55 – 1.48 (m, 1H), 1.41 (d, J = 17.0 Hz, 1H). 13 C NMR (101 MHz, Chloroform- d ) δ 149.6, 143.1, 138.6, 137.1, 136.6, 133.8, 129.5, 129.4,128.6, 128.5, 127.8, 127.7, 127.6, 127.3, 126.5, 126.3, 124.8, 121.1, 77.4,77.1, 76.7, 51.9, 32.6, 31.2, 27.9, 27.7, 26.4, 21.49. HRMS (ESI-TOF) m / z [M+ Na] + calcd for C 31 H 33 NO2SNa + 506.2124; found 506.2133.

[0060] Example 7

[0061] The preparation method of 3g of sulfonamide polyene compound in this embodiment is as follows: .

[0062] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 72% yield. The chromatographic information is as follows.

[0063] 1 H NMR (600 MHz, Chloroform- d ) δ 8.08 (t, J = 1.8 Hz, 1H), 7.86 – 7.81(m, 1H), 7.70 – 7.65 (m, 1H), 7.34 (d, J = 7.9 Hz, 1H), 7.32 – 7.28 (m, 4H), 7.24 (d, J = 14.2 Hz, 3H), 7.19 (d, J = 7.4 Hz, 1H), 7.12 – 7.05 (m, 2H), 6.93(d, J = 15.9 Hz, 1H), 6.42 (d, J = 15.7 Hz, 1H), 6.29 – 6.21 (m, 1H), 5.81 (d, J =15.9 Hz, 1H), 4.40 – 4.34 (m, 1H), 3.94 (dd, J = 14.5, 8.5 Hz, 1H), 2.53 – 2.42(m, 2H), 2.42 – 2.33 (m, 2H), 1.73 – 1.64 (m, 2H), 1.58 – 1.48 (m, 3H), 1.46– 1.39 (m, 1H). 13 C NMR (151 MHz, Chloroform- d) δ 149.6, 143.2, 136.8, 136.4,135.4, 134.4, 130.6, 130.4, 129.6, 128.7, 128.6, 127.9, 127.6, 127.5, 126.5,126.4, 126.3, 124.2, 123.0, 121.2, 77.3, 77.1, 76.8, 52.3, 32.6, 31.2, 27.9,27.7, 26.36. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 30 H 30 BrNO2SNa + 570.1073; found 570.1105.

[0064] Example 8

[0065] The preparation method of sulfonamide polyene compound 3h in this embodiment includes the following steps: .

[0066] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 80% yield. The chromatographic information is as follows.

[0067] 1 H NMR (600 MHz, Chloroform- d ) δ 7.61 (dd, J = 3.7, 1.4 Hz, 1H), 7.56(dd, J = 5.0, 1.4 Hz, 1H), 7.33 – 7.21 (m, 7H), 7.20 – 7.15 (m, 1H), 7.13 (dd, J = 7.2, 1.7 Hz, 2H), 7.08 (dd, J = 5.0, 3.7 Hz, 1H), 6.93 (d, J= 15.9 Hz, 1H), 6.42 (d, J = 15.7 Hz, 1H), 6.33 – 6.25 (m, 1H), 5.87 (d, J = 15.9 Hz, 1H), 4.50 –4.43 (m, 1H), 3.95 (dd, J = 14.5, 8.5 Hz, 1H), 2.54 – 2.34 (m, 4H), 1.72 – 1.65(m, 2H), 1.57 – 1.47 (m, 3H), 1.45 – 1.37 (m, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ 149.8, 142.6, 137.1, 136.5, 134.2, 132.0, 131.3, 129.3,128.7, 128.6, 127.9, 127.6, 127.5, 127.4, 126.5, 126.4, 124.5, 121.1, 52.1,32.6, 31.2, 27.9, 27.7, 26.3. HRMS (ESI-TOF) m / z: [M + Na] + calcd forC 28 H 29 NO2S2Na + 498.1532; found 498.1535.

[0068] Example 9

[0069] The preparation method of sulfonamide polyene compound 3i in this embodiment includes the following steps: .

[0070] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 72% yield. The chromatographic information is as follows.

[0071] 1H NMR (400 MHz, Chloroform- d ) δ 7.42 (d, J = 7.6 Hz, 2H), 7.35 – 7.28(m, 6H), 7.24 (q, J = 6.3 Hz, 1H), 7.09 (d, J = 15.8 Hz, 2H), 6.60 (d, J = 15.8 Hz, 1H), 6.51 (d, J = 15.7 Hz, 1H), 6.30 (dt, J = 15.3, 7.2 Hz, 1H), 4.34 (dd, J =14.6, 6.4 Hz, 1H), 4.09 (dd, J = 14.6, 8.0 Hz, 1H), 3.05 (s, 3H), 2.61 – 2.37(m, 4H), 1.72 – 1.66 (m, 2H), 1.62 – 1.42 (m, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 148.8, 137.2, 136.4, 134.4, 129.2, 128.8, 128.7, 128.1,128.0, 127.6, 126.5, 124.4, 122.5, 77.4, 52.4, 41.4, 32.5, 31.1, 27.9, 27.7,26.4. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 25 H 29 NO2SNa + 430.1811; found 430.1817.

[0072] Example 10

[0073] The preparation method of sulfonamide polyene compound 3j in this embodiment includes the following steps: .

[0074] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) to obtain a sulfonamide polyene compound in 49% yield. The chromatographic information is as follows.

[0075] 1 H NMR (400 MHz, Chloroform- d ) δ 7.42 (d, J = 7.6 Hz, 2H), 7.35 – 7.28(m, 6H), 7.24 (q, J = 6.3 Hz, 1H), 7.09 (d, J = 15.8 Hz, 2H), 6.60 (d, J = 15.8 Hz, 1H), 6.51 (d, J = 15.7 Hz, 1H), 6.32 – 6.27 (m, 1H), 4.34 (dd, J = 14.6, 6.4 Hz, 1H), 4.09 (dd, J = 14.6, 8.0 Hz, 1H), 3.05 (s, 3H), 2.61 – 2.37 (m, 4H), 1.72 –1.66 (m, 2H), 1.62 – 1.42 (m, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 148.8,137.2, 136.4, 134.4, 129.2, 128.8, 128.7, 128.1, 128.0, 127.6, 126.5, 124.4,122.5, 77.4, 52.4, 41.4, 32.5, 31.1, 27.9, 27.7, 26.4. HRMS (ESI-TOF) m / z: [M+ Na] + calcd for C 26 H 31 NO2SNa + 444.1968; found 444.1969.

[0076] Example 11

[0077] The preparation method of sulfonamide polyene compound 3k in this embodiment includes the following steps: .

[0078] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 76% yield. The chromatographic information is as follows.

[0079] 1 H NMR (600 MHz, Chloroform- d ) δ 7.95 – 7.89 (m, 2H), 7.59 – 7.53 (m,1H), 7.47 (t, J = 7.7 Hz, 2H), 7.31 – 7.26 (m, 4H), 7.24 – 7.19 (m, 1H), 7.04(d, J = 7.8 Hz, 2H), 6.93 (d, J = 7.8 Hz, 2H), 6.86 (d, J = 15.9 Hz, 1H), 6.38 (d, J = 15.8 Hz, 1H), 6.30 – 6.22 (m, 1H), 5.70 (d, J = 15.9 Hz, 1H), 4.44 – 4.37 (m,1H), 3.89 (dd, J = 14.5, 8.4 Hz, 1H), 2.53 – 2.46 (m, 1H), 2.47 – 2.40 (m, 2H), 2.40 – 2.34 (m, 1H), 2.30 (s, 3H), 1.73 – 1.65 (m, 2H), 1.56 – 1.47 (m, 3H),1.42 – 1.38 (m, 1H). 13 C NMR (151 MHz, Chloroform-d ) δ 148.9, 141.5, 137.3,136.6, 134.3, 133.9, 132.3, 129.4, 129.2, 128.9, 128.6, 127.8, 127.7, 126.5,126.2, 124.7, 120.2, 77.3, 77.1, 76.9, 52.0, 32.6, 31.2, 27.9, 27.7, 26.4,21.2. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 31 H 33 NO2SNa + 506.2124; found 506.2131.

[0080] Example 12

[0081] The preparation method of sulfonamide polyene compound 3l in this embodiment includes the following steps: .

[0082] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) to obtain a sulfonamide polyene compound in 93% yield. The chromatographic information is as follows.

[0083] 1 H NMR (400 MHz, Chloroform- d ) δ 7.93 (d, J = 5.9 Hz, 2H), 7.63 – 7.55(m, 1H), 7.54 – 7.44 (m, 4H), 7.28 (d, J = 4.3 Hz, 4H), 7.28 – 7.19 (m, 1H), 7.13 (d, J = 8.0 Hz, 2H), 7.03 (d, J = 15.9 Hz, 1H), 6.40 (d, J= 15.7 Hz, 1H), 6.31 – 6.19 (m, 1H), 5.81 (d, J = 15.8 Hz, 1H), 4.40 (dd, J = 14.4, 5.9 Hz, 1H), 3.93 (dd, J = 14.5, 8.3 Hz, 1H), 2.59 – 2.43 (m, 2H), 2.45 – 2.31 (m, 2H), 1.76– 1.64 (m, 2H), 1.55 (d, J = 6.2 Hz, 3H), 1.48 – 1.35 (m, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ 151.4, 141.4, 140.6, 136.4, 134.2, 132.5, 131.3, 129.1,129.0, 128.9 (q, J = 32.2 Hz), 128.7, 128.6, 128.5, 127.9, 127.6, 126.4, 126.3,125.4 (q, J = 3.8 Hz), 124.4, 124.2 (q, J = 271.8 Hz), 123.8, 52.1, 32.7, 31.3,27.9, 27.7, 26.3. 19 F NMR (376 MHz, Chloroform- d ) δ -62.40. HRMS (ESI-TOF) m / z:[M + Na] + calcd for C 31 H 30 F3NO2SNa + 560.1842; found 560.1847.

[0084] Example 13

[0085] The preparation method of sulfonamide polyene compound 3m in this embodiment includes the following steps: .

[0086] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 82% yield. The chromatographic information is as follows.

[0087] 1 H NMR (400 MHz, Chloroform- d ) δ 7.95 – 7.88 (m, 2H), 7.55 – 7.46 (m,1H), 7.46 – 7.39 (m, 2H), 7.33 – 7.24 (m, 4H), 7.23 – 7.18 (m, 2H), 7.18 –7.12 (m, 1H), 7.01 (d, J = 16.1 Hz, 1H), 6.85 (t, J = 7.5 Hz, 1H), 6.77 (d, J = 8.3Hz, 1H), 6.40 (d, J = 15.8 Hz, 1H), 6.33 – 6.21 (m, 2H), 4.42 – 4.24 (m, 1H), 4.00 (dd, J = 14.6, 8.2 Hz, 1H), 3.65 (s, 3H), 2.55 – 2.30 (m, 4H), 1.77 – 1.64(m, 2H), 1.52 (d, J = 28.1 Hz, 3H), 1.47 – 1.32 (m, 1H). 13 C NMR (101 MHz, Chloroform- d) δ 156.8, 148.5, 141.3, 136.7, 133.8, 132.1, 128.7, 128.6,128.5, 128.3, 127.8, 127.7, 126.7, 126.5, 126.0, 124.9, 124.8, 121.9, 120.5,110.7, 77.4, 55.2, 52.1, 32.6, 31.2, 27.9, 27.7, 26.5. HRMS (ESI-TOF) m / z: [M+ Na] + calcd for C 31 H 33 NO3SNa + 522.2073; found 522.2079.

[0088] Example 14

[0089] The preparation method of sulfonamide polyene compound 3n in this embodiment includes the following steps: .

[0090] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 80% yield. The chromatographic information is as follows.

[0091] 1 H NMR (600 MHz, Chloroform- d ) δ 7.95 – 7.90 (m, 2H), 7.59 – 7.56 (m,1H), 7.49 (t, J = 7.8 Hz, 2H), 7.32 – 7.27 (m, 4H), 7.24 – 7.20 (m, 1H), 7.14(t, J = 7.9 Hz, 1H), 6.90 (d, J = 15.9 Hz, 1H), 6.75 – 6.70 (m, 1H), 6.69 – 6.64(m, 1H), 6.53 (t, J= 2.1 Hz, 1H), 6.39 (d, J = 15.7 Hz, 1H), 6.30 – 6.23 (m,1H), 5.70 (d, J = 15.9 Hz, 1H), 4.44 – 4.37 (m, 1H), 3.90 (dd, J = 14.5, 8.4 Hz,1H), 3.76 (s, 3H), 2.53 – 2.47 (m, 1H), 2.47 – 2.40 (m, 2H), 2.40 – 2.33 (m,1H), 1.72 – 1.66 (m, 2H), 1.56 – 1.48 (m, 3H), 1.44 – 1.37 (m, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ 159.8, 149.8, 141.5, 138.5, 136.5, 134.0, 132.4,129.4, 129.0, 128.6, 127.8, 127.7, 126.5, 124.7, 121.6, 118.9, 113.1, 111.7,77.1, 55.2, 52.0, 32.6, 31.2, 27.9, 27.7, 26.4. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 31 H 33 NO3SNa + 522.2073; found 522.2070.

[0092] Example 15

[0093] The preparation method of sulfonamide polyene compound 3o in this embodiment includes the following steps: .

[0094] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 80% yield. The chromatographic information is as follows.

[0095] 1 H NMR (600 MHz, Chloroform- d ) δ 7.94 – 7.89 (m, 2H), 7.59 – 7.54 (m,1H), 7.47 (t, J = 7.8 Hz, 2H), 7.31 – 7.26 (m, 4H), 7.23 (d, J = 18.0 Hz, 1H),7.01 – 6.94 (m, 2H), 6.80 – 6.74 (m, 3H), 6.39 (dd, J = 15.8, 1.3 Hz, 1H), 6.30– 6.22 (m, 1H), 5.70 (d, J = 15.9 Hz, 1H), 4.43 – 4.36 (m, 1H), 3.90 (dd, J =16.5, 8.4 Hz, 1H), 3.78 (s, 3H), 2.52 – 2.46 (m, 1H), 2.46 – 2.39 (m, 2H), 2.39 – 2.32 (m, 1H), 1.72 – 1.65 (m, 2H), 1.56 – 1.46 (m, 3H), 1.43 – 1.36(m, 1H). 13 C NMR (101 MHz, Chloroform- d) δ 159.1, 148.2, 141.4, 136.6, 133.9,132.3, 129.8, 129.0, 128.9, 128.6, 127.8, 127.7, 127.5, 126.5, 124.8, 119.2,114.0, 77.4, 77.1, 76.8, 55.30, 52.0, 32.6, 31.2, 27.9, 27.7, 26.4. HRMS(ESI-TOF) m / z: [M + Na] + calcd for C 31 H 33 NO3SNa + 522.2073; found 522.2080.

[0096] Example 16

[0097] The preparation method of sulfonamide polyene compound 3p in this embodiment includes the following steps: .

[0098] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 82% yield. The chromatographic information is as follows.

[0099] 1 H NMR (400 MHz, Chloroform- d ) δ 7.95 (d, J = 7.7 Hz, 2H), 7.78 – 7.65(m, 3H), 7.58 (t, J = 7.4 Hz, 1H), 7.48 (t, J = 7.7 Hz, 2H), 7.46 – 7.33 (m, 3H), 7.28 (q, J = 6.9, 6.4 Hz, 5H), 7.22 (d, J = 7.2 Hz, 1H), 7.05 (d, J= 15.7 Hz, 1H), 6.41 (d, J = 15.7 Hz, 1H), 6.35 – 6.23 (m, 1H), 5.93 (d, J = 15.8 Hz, 1H), 4.44(dd, J = 14.5, 5.7 Hz, 1H), 3.96 (dd, J = 14.5, 8.2 Hz, 1H), 2.63 – 2.34 (m, 4H), 1.79 – 1.65 (m, 2H), 1.61 – 1.49 (m, 3H), 1.48 – 1.32 (m, 1H). 13 C NMR (101MHz, Chloroform- d ) δ 149.7, 141.5, 136.6, 134.5, 134.1, 133.6, 132.9, 132.4,129.7, 129.0, 128.6, 128.1, 128.0, 127.9, 127.8, 127.7, 126.5, 126.4, 126.3,125.8, 124.7, 123.4, 121.6, 52.1, 32.7, 31.3, 28.0, 27.8, 26.4. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 34 H 33 NO2SNa + 542.2124; found 542.2108.

[0100] Example 17

[0101] The preparation method of sulfonamide polyene compound 3q in this embodiment includes the following steps: .

[0102] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 85% yield. The chromatographic information is as follows.

[0103] 1 1H NMR (600 MHz, Chloroform- d ) δ 7.93 (dd, J J = 8.2, 1.3 Hz, 2H), 7.64 –7.55 (m, 1H), 7.49 (t, J J = 7.8 Hz, 2H), 7.35 – 7.21 (m, 4H), 7.20 – 7.14 (m, 3H), 7.09 – 7.00 (m, 1H), 6.69 (d, J J = 16.0 Hz, 2H), 6.39 (d, J J = 15.7 Hz, 1H), 6.31 – 6.21 (m, 1H), 5.69 (d, J J = 16.0 Hz, 1H), 4.38 (dd, J J = 14.4, 5.9 Hz, 1H), 3.94 (dd, J J = 14.4, 8.3 Hz, 1H), 2.62 (dd, J J = 17.4, 8.1 Hz, 2H), 2.50 (dd, J J = 17.5, 7.6 Hz, 2H), 1.83 – 1.64 (m, 3H), 1.51 – 1.39 (m, 1H). 13 13C NMR (151 MHz, Chloroform- d ) δ 155.1, 141.6, 137.0, 136.5, 133.8, 132.4, 128.9, 128.6, 128.5, 127.8, 127.6, 127.5, 127.3, 126.5, 126.4, 126.3, 124.6, 123.2, 77.0, 51.6, 33.7, 31.1, 26.3, 26.2. HRMS (ESI-TOF) m / z: [M + K] + calcd for C 29 H 29 NO2SK + 494.1511; found 494.1554.

[0104] Example 18

[0105] The preparation method of sulfonamide polyene compound 3r in this embodiment includes the following steps: .

[0106] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 77% yield. The chromatographic information is as follows.

[0107] 1 H NMR (400 MHz, Chloroform- d ) δ 7.97 – 7.89 (m, 2H), 7.62 – 7.53 (m,1H), 7.53 – 7.44 (m, 2H), 7.28 (d, J = 4.2 Hz, 4H), 7.28 – 7.19 (m, 3H), 7.22 –7.13 (m, 1H), 7.09 – 7.02 (m, 2H), 6.87 (d, J = 15.9 Hz, 1H), 6.39 (d, J = 15.7Hz, H), 6.33 – 6.19 (m, H), 5.74 (d, J = 15.9 Hz, 1H), 4.49 – 4.35 (m, 1H), 3.93 (dd, J = 14.5, 8.2 Hz, 1H), 1.99 (s, 3H), 1.92 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 142.1, 141.5, 137.0, 136.6, 133.9, 132.4, 130.5, 129.1,129.0, 128.6, 128.5, 127.8, 127.7, 127.4, 126.5, 126.3, 124.5, 121.8, 77.4,77.1, 76.7, 52.0, 23.2, 20.7. HRMS (ESI-TOF) m / z: [M + Na]+ calcd forC 27 H 27 NO2SNa + 452.1655; found 452.1656.

[0108] Example 19

[0109] The preparation method of sulfonamide polyene compound 3s in this embodiment includes the following steps: .

[0110] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) to obtain a sulfonamide polyene compound in 93% yield. The chromatographic information is as follows.

[0111] 1 H NMR (600 MHz, Chloroform- d ) δ 7.85 (dd, J = 7.8, 1.6 Hz, 2H), 7.61 –7.54 (m, 1H), 7.50 (dd, J = 8.4, 7.0 Hz, 2H), 7.34 – 7.21 (m, 5H), 6.42 (d, J =15.8 Hz, 1H), 5.93 (dd, J = 15.8, 13.4 Hz, 1H), 5.72 – 5.57 (m, 1H), 5.21 –5.08 (m, 1H), 3.98 (dd, J = 6.7, 1.3 Hz, 2H), 3.86 (d, J = 6.3 Hz, 2H). 13 C NMR (151 MHz, Chloroform- d) δ 140.5, 136.2, 134.1, 132.7, 132.5, 129.1, 128.6,127.9, 127.2, 126.4, 123.7, 119.1, 49.5, 49.0. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 18 H 19 NO2SNa + 336.1029; found 336.1038.

[0112] Example 20

[0113] The preparation method of sulfonamide polyene compound 3t in this embodiment includes the following steps: .

[0114] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 83% yield. The chromatographic information is as follows.

[0115] 1 H NMR (600 MHz, Chloroform- d ) δ 7.95 – 7.89 (m, 2H), 7.62 – 7.56 (m,1H), 7.53 (d, J = 8.1 Hz, 2H), 7.49 (t, J = 7.8 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H), 7.23 (t, J = 7.5 Hz, 1H), 7.20 – 7.14 (m, 2H), 7.07 – 7.00 (m, 2H), 6.92 (d, J =15.9 Hz, 1H), 6.46 – 6.36 (m, 1H), 5.72 (d, J = 15.9 Hz, 1H), 4.42 (dd, J= 14.6, 5.0 Hz, 1H), 3.92 (dd, J = 14.7, 7.4 Hz, 1H), 2.55 – 2.34 (m, 4H), 1.75 – 1.67(m, 2H), 1.58 – 1.48 (m, 3H), 1.42 – 1.34 (m, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ 149.7, 141.3, 140.0, 136.9, 132.5, 132.5, 129.6, 129.0,128.6, 127.8, 127.7 127.6 (q, J = 26.5 Hz), 127.5, 126.6, 126.2, 125.6 (q, J =3.9 Hz), 124.1 (q, J = 271.9 Hz), 123.2, 77.2, 77.0, 76.8, 51.8, 32.6, 31.2,27.9, 27.7, 26.3. 19 F NMR (565 MHz, Chloroform- d ) δ -62.48. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 31 H 30 F3NO2SNa + 560.1842; found 560.1845.

[0116] Example 21

[0117] The preparation method of sulfonamide polyene compound 3u in this embodiment includes the following steps: .

[0118] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) to obtain a sulfonamide polyene compound in 48% yield. The chromatographic information is as follows.

[0119] 1 H NMR (600 MHz, Chloroform- d ) δ 8.02 – 7.88 (m, 2H), 7.56 (d, J = 16.1Hz, 1H), 7.47 (t, J = 7.8, 7.8 Hz, 2H), 7.31 – 7.26 (m, 4H), 7.25 – 7.19 (m,1H), 6.99 – 6.96 (m, 2H), 6.79 – 6.73 (m, 3H), 6.39 (dd, J = 15.8, 1.3 Hz, 1H), 6.33 – 6.20 (m, 1H), 5.70 (d, J = 15.9 Hz, 1H), 4.46 – 4.29 (m, 1H), 3.93 –3.86 (m, 1H), 3.78 (s, 3H), 2.53 – 2.28 (m, 4H), 1.71 – 1.61 (m, 2H), 1.55(d, J = 3.8 Hz, 3H), 1.41 (d, J = 4.4 Hz, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ159.4, 149.5, 141.5, 137.1, 133.5, 132.3, 129.4, 129.3, 128.9, 128.5, 127.8,127.7, 127.3, 126.2, 122.3, 121.2, 114.0, 55.3, 52.1, 32.6, 31.2, 27.9, 27.7,26.4. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 31 H 33 NO3SNa + 522.2073; found522.2089.

[0120] Example 22

[0121] The preparation method of sulfonamide polyene compound 3v in this embodiment includes the following steps: .

[0122] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) to obtain a sulfonamide polyene compound in 48% yield. The chromatographic information is as follows.

[0123] 1 H NMR (600 MHz, Chloroform- d ) δ 8.02 – 7.88 (m, 2H), 7.56 (d, J = 16.1Hz, 1H), 7.47 (t, J = 7.8, 7.8 Hz, 2H), 7.31 – 7.26 (m, 4H), 7.25 – 7.19 (m,1H), 6.99 – 6.96 (m, 2H), 6.79 – 6.73 (m, 3H), 6.39 (dd, J = 15.8, 1.3 Hz, 1H), 6.33 – 6.20 (m, 1H), 5.70 (d, J = 15.9 Hz, 1H), 4.46 – 4.29 (m, 1H), 3.93 –3.86 (m, 1H), 3.78 (s, 3H), 2.53 – 2.28 (m, 4H), 1.71 – 1.61 (m, 2H), 1.55(d, J = 3.8 Hz, 3H), 1.41 (d, J = 4.4 Hz, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ159.4, 149.5, 141.5, 137.1, 133.5, 132.3, 129.4, 129.3, 128.9, 128.5, 127.8,127.7, 127.3, 126.2, 122.3, 121.2, 114.0, 55.3, 52.1, 32.6, 31.2, 27.9, 27.7,26.4. HRMS (ESI-TOF) m / z: [M + Na] +calcd for C 31 H 33 NO3SNa + 522.2073; found522.2089.

[0124] Example 23

[0125] The preparation method of sulfonamide polyene compound 3w in this embodiment includes the following steps: .

[0126] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 89% yield. The chromatographic information is as follows.

[0127] 1 H NMR (600 MHz, Chloroform- d ) δ 7.97 (d, J = 7.7 Hz, 2H), 7.62 (t, J =7.5, 7.5 Hz, 1H), 7.52 (t, J = 7.6, 7.6 Hz, 2H), 7.36 (t, J = 7.5, 7.5 Hz, 2H), 7.29 (t, J = 7.5, 7.5 Hz, 1H), 7.23 (t, J = 7.5, 7.5 Hz, 2H), 7.17 (dd, J = 15.9,7.5 Hz, 3H), 7.04 – 7.00 (m, 2H), 6.86 (d, J = 16.0 Hz, 1H), 6.51 (s, 1H), 5.66(d, J = 16.1 Hz, 1H), 4.43 (d, J = 14.4 Hz, 1H), 3.94 (d, J = 14.4 Hz, 1H), 3.60(d, J= 16.7 Hz, 1H), 3.38 (d, J = 16.8 Hz, 1H), 2.60 – 2.42 (m, 2H), 2.40 – 2.31(m, 1H), 2.27 – 2.12 (m, 1H), 1.78 – 1.46 (m, 5H), 1.44 – 1.32 (m, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ 150.3, 140.7, 136.6, 136.4, 135.2, 132.9, 130.2,129.2, 128.8, 128.6, 128.4, 128.1, 127.9, 127.7, 127.1, 126.4, 126.3, 120.3,117.8, 53.8, 32.5, 31.5, 28.0, 27.7, 26.3, 18.8. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 24 H 27 NO2SK + 432.1394; found 432.1369.

[0128] Example 24

[0129] The preparation method of sulfonamide polyene compound 3x in this embodiment includes the following steps: .

[0130] A magnetic stir bar, sulfonamide (0.1 mmol), allyl carbonate (0.2 mmol), tetrakis(triphenylphosphine)palladium (0.01 mmol), and ethyl acetate (1.0 mL) were added sequentially to a reaction tube. The reaction was carried out at room temperature with stirring in air for 4 hours. After the reaction was complete, 20 mL of saturated sodium chloride solution was added, followed by extraction with dichloromethane (30 mL × 3). The organic phase was collected and purified by silica gel column chromatography using petroleum ether (PE) and ethyl acetate (EA) (v / v ratio 10:1) as eluents to obtain a sulfonamide polyene compound in 35% yield. The chromatographic information is as follows.

[0131] 1 H NMR (600 MHz, Chloroform- d ) δ 7.91 (d, J = 7.7 Hz, 2H), 7.57 (t, J=7.3, 7.3 Hz, 1H), 7.48 (t, J = 7.6, 7.6 Hz, 2H), 7.31 (s, 1H), 7.23 (t, J = 7.4, 7.4 Hz, 2H), 7.16 (t, J = 7.3, 7.3 Hz, 1H), 7.03 (d, J = 7.6 Hz, 2H), 6.90 (d, J =15.8 Hz, 1H), 6.37 – 6.30 (m, 1H), 6.27 – 6.09 (m, 3H), 5.73 (d, J = 15.9 Hz, 1H), 4.39 (dd, J = 14.6, 5.8 Hz, 1H), 3.86 (dd, J = 14.5, 7.9 Hz, 1H), 2.61 –2.49 (m, 1H), 2.49 – 2.39 (m, 2H), 2.39 – 2.27 (m, 1H), 1.78 – 1.65 (m, 2H),1.64 – 1.47 (m, 3H), 1.47 – 1.36 (m, 1H). 13 C NMR (151 MHz, Chloroform- d ) δ152.1, 149.6, 142.2, 141.4, 137.1, 132.3, 129.4, 128.9, 128.4, 127.7, 127.6,127.3, 126.2, 123.2, 122.3, 121.1, 111.2, 108.1, 51.6, 32.6, 31.2, 27.9,27.5, 26.4. HRMS (ESI-TOF) m / z: [M + Na] + calcd for C 28 H 29 NO3SNa + 482.1760; found 482.1769.

[0132] Example 1 of the experimental results.

[0133] In vitro antibacterial activity test.

[0134] The steps for testing the antibacterial rate are as follows: The test was conducted according to QB / T 2738-2023, section 7.3. 0.1 g of sample was added to a sterile test tube containing the test bacteria, along with 5 mL of sterile water. The mixture was stirred for 10 min, and the antibacterial rate was then tested. The test bacteria were common Staphylococcus aureus (Gram-positive bacteria) and Escherichia coli (Gram-negative bacteria). Results are shown below. Figure 1 and 2 .

[0135] Test results: From Figure 1 and Figure 2 As can be seen, target products 3a, 3b, 3c, 3d, and 3e all exhibit extremely strong and broad-spectrum antibacterial activity against two common pathogenic bacteria—Staphylococcus aureus and Escherichia coli—with inhibition rates reaching or exceeding 99.98%, demonstrating excellent antibacterial application potential. Specific data are as follows... Figure 1 and 2 As shown.

[0136] Example 2 of the test results.

[0137] In vitro antioxidant activity experiment.

[0138] (1) Determination of DPPH free radical scavenging ability.

[0139] Test Principle: DPPH (1,1-diphenyl-2-picrylhydrazine) is a stable nitrogen-centered free radical. Its ethanol solution is purple, with a maximum absorption wavelength of 517 nm. When a free radical scavenger is added to the DPPH solution, its single electrons are captured, causing the solution color to lighten to yellow or pale yellow, and the absorbance at 517 nm to decrease. The degree of change is linearly related to the degree of free radical scavenging. Therefore, this experimental method can be expressed as a scavenging rate; the higher the scavenging rate, the stronger the antioxidant capacity of the substance.

[0140] DPPH scavenging rate determination procedure: Accurately weigh 5 mg DPPH, dissolve it in anhydrous ethanol, and dilute to a final volume of 250 mL in a volumetric flask. First, take 0.5 mL of each sample solution of different concentrations and add an equal volume of 5 × 10⁻⁶ ethanol. -5 Prepare a 1 mol / L DPPH solution, shake well, and let stand at room temperature in the dark for 30 min. Use distilled water as a blank instead of the sample solution and measure its absorbance at 517 nm. Use vitamin C as a control group. Calculate the DPPH free radical scavenging rate (%) for each sample using the following formula.

[0141] .

[0142] In the formula: P – Clearance rate; A0 — Absorbance of distilled water + DPPH solution; A x—The absorbance of the sample solution + DPPH solution; A x0 —The absorbance of the sample solution to be tested plus anhydrous ethanol (the same volume as the DPPH solution).

[0143] Test results are available Figure 3 .from Figure 3 As can be seen, at the highest tested concentration (1.0 mg / mL), the scavenging activities of each sample, from highest to lowest, are: 3b > 3a > 3c > 3d > 3e. Samples 3a and 3b exhibit concentration dependence, meaning that the scavenging rate increases with increasing concentration, indicating that their antioxidant activity is dose-dependent. The concentration-dependent curves of the target products show that their free radical scavenging efficacy is directly related to the effective molecular concentration, consistent with the action mode of most synthetic or natural antioxidants. Among them, compound 3b achieved a scavenging rate of over 60% for DPPH free radicals at a concentration of 1.0 mg / mL, demonstrating excellent antioxidant activity.

[0144] (2) Determination of ABTS free radical scavenging ability.

[0145] Test principle: ABTS is oxidized into colored free radicals ABTS in the presence of oxidants such as H2O2 and K2S2O8. + At this point, it has the maximum absorbance value at a certain wavelength. When antioxidants are present, ABTS... + The reaction color becomes lighter and the absorbance value decreases. The change in absorbance reflects the antioxidant capacity of the analyte.

[0146] ABTS clearance rate: First, prepare 7 mmol / L ABTS reagent, then prepare 2.45 mmol / L K2S2O8 solution. Mix the two solutions at a 1:1 volume ratio and let them react in the dark for 16 h to obtain the ABTS working solution.

[0147] Dilute 0.5 mL of ABTS working solution with PBS (pH=7.0) to a certain factor, adjusting its absorbance at 734 nm to 0.70±0.05. Take 200 μL of sample solutions of different concentrations, add 1.2 mL of diluted ABTS working solution, mix well, and let stand at room temperature for 10 min. Use an equal volume of distilled water instead of sample solution as a blank, and use a vitamin C solution of the same concentration as a control group. Record the absorbance of the reaction solution at 734 nm, and calculate the scavenging rate of ABTS free radicals by the sample according to the following formula.

[0148] .

[0149] In the formula: P – Clearance rate; A0 — Absorbance of distilled water + ABTS solution; A x —The absorbance of the sample solution + ABTS solution; A x0 —Absorbance of the sample solution + PBS (pH=7.0) solution.

[0150] See results Figure 4 Target products 3a and 3d exhibited excellent antioxidant activity, with similar scavenging rates at a concentration of 1.0 mg / mL; while 3c and 3e showed relatively weaker scavenging effects. The scavenging rates of all target products were concentration-dependent. As synthetic target products, 3a and 3d demonstrated activity comparable to the classic antioxidant vitamin C in the ABTS model, suggesting they possess strong electron or hydrogen atom donation capabilities and are potential antioxidant candidates.

[0151] Example 3 of the experimental results.

[0152] Cytotoxicity assay.

[0153] Test method: HaCaT cell proliferation assay, the specific steps are as follows: HaCaT cells were cultured in DMEM medium supplemented with 10% fetal bovine serum and 1% penicillin-streptomycin at 37 °C for 24 h, digested with 0.25% trypsin, collected by centrifugation, and divided into 5 × 10⁶ wells in 96-well plates. 4 Cells / mL, 100 μL / well; after incubation at 37℃, 5% CO2 for 24 hours, the supernatant was discarded, and the cells were co-cultured at final sample concentrations of 2.5 mg / mL. After 24 hours, the supernatant was discarded, and 10 μL of CCK-8 stock solution (usually 10% of the cell culture volume) was added in the dark, taking care not to introduce air bubbles to avoid interfering with the readings. After incubation in the incubator for 2 hours, the absorbance was measured using a microplate reader at 37℃ and 450 nm. Three independent experiments were performed to produce the percentage growth relative to untreated control cells. Results are shown below. Figure 5 and 6 .

[0154] Test results: From Figure 5 and Figure 6As can be seen, target products 3b and 3c exhibited excellent safety within the tested concentration range and may have a certain effect on promoting cell viability; while product 3d showed clear cytotoxicity at high concentrations (5 mg / mL). Specifically, at a concentration of 2.5 mg / mL: the cell viability (109%-133%) of all products (3a-3d) was above 100%, indicating that they were not cytotoxic at this concentration and may have a slight promoting effect on cell viability. At a concentration of 5 mg / mL, the viability of product 3a also decreased significantly to 105%, although it was still above 100%, it was close to the edge of toxicity, suggesting that its safety window was narrow and caution should be exercised when increasing the concentration. The viability of products 3b and 3c remained stable (128% and 126%, respectively), which was basically consistent with the results at low concentrations, indicating that they had good tolerability and safety in the concentration range of 2.5-5 mg / mL.

[0155] The above description represents the preferred embodiments of the present invention. It should be noted that those skilled in the art can make various improvements and modifications without departing from the principles of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. A sulfonamide polyene compound, characterized in that, The structural formula of the sulfonamide polyene compound is shown below: ,in, R 1 for: any of them, R 2 for: ; R 3 for: any of them, R 4 for: .

2. The method for preparing the sulfonamide polyene compound according to claim 1, characterized in that, Includes the following steps: After mixing sulfonamide compound 1, allyl carbonate 2, tetrakis(triphenylphosphine)palladium and solvent, the mixture was reacted in air at room temperature with stirring for 3-6 h. After the reaction was completed, saturated sodium chloride solution was added first, followed by extraction with dichloromethane. The organic phase was collected and purified by silica gel column chromatography to obtain sulfonamide polyene compound 3. The synthesis route is shown below: 。 3. The method for preparing the sulfonamide polyene compound as described in claim 2, characterized in that, The molar ratio of sulfonamide compound 1 to allyl carbonate 2 is 1:2-2.

2.

4. The method for preparing the sulfonamide polyene compound as described in claim 2, characterized in that, The molar ratio of the sulfonamide compound 1 to tetrakis(triphenylphosphine)palladium is 1:0.08-0.

15.

5. The method for preparing the sulfonamide polyene compound as described in claim 2, characterized in that, The solvent is ethyl acetate, and 1-2 mL of solvent is added for every 0.1 mmol of sulfonamide compound 1.

6. The use of the sulfonamide polyene compound of claim 1 in the preparation of antibacterial drugs.

7. The use of the sulfonamide polyene compound of claim 1 in the preparation of antioxidant drugs.

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