Silicon-containing conjugated olefin compound as well as preparation method and application thereof

Abstract

The invention discloses a silicon-containing conjugated olefin compound as well as a preparation method and application thereof, the structural formula of the silicon-containing conjugated olefin compound is shown as (I), and the silicon-containing conjugated olefin compound is obtained by carrying out silicon-carbon bond breakage synthesis on an allenyl functionalized silicon hybrid quaternary compound in the presence of a ligand, a palladium catalyst and a reaction medium, the allene functionalized silicon hybrid quaternary compound is used as a reactant to directly perform intramolecular reaction under the action of a complex formed by a metal catalyst and a phosphine ligand, the reaction condition is mild, the method is simple, and the obtained crude product can be purified by a silica gel rapid chromatography to obtain a pure product. The method has the advantages of mild reaction conditions, wide substrate expansion range, simple preparation operation and the like, and the prepared compound has a certain application prospect in the anti-tumor field.

Description

Technical Field

[0001] This invention relates to the field of organic chemistry, specifically to a silicon-containing conjugated olefin compound, its preparation method, and its applications. Background Technology

[0002] In the development of antitumor compounds, silicon-containing compounds have gradually become a research focus due to their unique physicochemical properties and biological activities. Among them, silicon-containing conjugated olefin compounds, as a class of molecules that combine the characteristics of silicon atoms with the structural advantages of conjugated olefins, provide a new approach to tumor treatment.

[0003] The uniqueness of silicon-containing conjugated olefin compounds stems from the synergistic effect between silicon atoms and the conjugated olefin skeleton. The conjugated olefin structure forms a stable conjugated system through the delocalization of π electrons, endowing the molecule with good electron transfer ability and structural flexibility. This makes it easy for it to interact specifically with biomolecules. The introduction of silicon atoms can regulate the lipophilicity, polarity, and spatial configuration of the molecule, and can change the charge distribution of the molecule through inductive effects, thereby enhancing its binding affinity to the target site.

[0004] However, research on silicon-containing conjugated olefin compounds still faces challenges: the synthetic routes of some compounds are complex and the yields are low, which limits their large-scale preparation.

[0005] Therefore, developing a silicon-containing conjugated olefin compound with low raw material cost, easy availability, simple synthesis process, and broad substrate range, as well as its preparation method, has become an urgent technical problem to be solved in this field. Summary of the Invention

[0006] The purpose of this invention is to address the shortcomings of existing technologies by providing a silicon-containing conjugated olefin compound, its preparation method, and its applications. The raw materials required by this invention are low in cost and readily available, and the synthesis process is simple with a wide substrate range.

[0007] This invention is achieved through the following technical solution: In a first aspect, the present invention provides a silicon-containing conjugated olefin compound having the structural formula shown in formula (I): Among them, R 1 It is hydrogen or halogen; R 2 It is a cycloalkyl, phenyl, or substituted phenyl; the substitution is selected from C. 1-4 One of alkyl, aryl, or halogen.

[0008] Secondly, this invention provides a method for preparing the above-mentioned silicon-containing conjugated olefin compounds. The reaction conditions are mild, the method is simple, and it can obtain silicon-containing conjugated olefin compounds with various substituents. The preparation method involves synthesizing silicon-containing conjugated olefin compounds through an intramolecular reaction of an allenyl-functionalized silicon-containing quaternary compound. The reaction formula is shown below: The specific reaction steps are as follows: In an inert gas atmosphere, phosphine ligands, palladium catalysts, and solvents were mixed, and then allene-functionalized silicon heterotetram compound 1 was added. After the reaction was completed, the solvent was removed under vacuum, and the resulting product was purified to obtain a silicon-containing conjugated olefin compound.

[0009] Preferably, the concentration of the reactant alkenyl-functionalized silicon heterotetramer is 0.1 mol / L.

[0010] Preferably, the palladium catalyst is palladium acetate, and the amount used is 3%-6% of the molar amount of allenyl-functionalized silicon heterotetram compound 1 (the molar ratio of allenyl-functionalized silicon heterotetram compound 1 to the catalyst is 1:0.03-0.06).

[0011] Preferably, the phosphine ligand is 1,1'-bis(diphenylphosphine)ferrocene.

[0012] Preferably, the amount of the phosphine ligand used is 1%-5% of the molar amount of allenyl-functionalized silicon heterotetram 1 (the molar ratio of allenyl-functionalized silicon heterotetram 1 to the phosphine ligand is 1:0.01-0.05).

[0013] Preferably, the solvent is 1,4-dioxane.

[0014] Preferably, the reaction temperature is 40-100 ℃ and the reaction time is 10-24 h.

[0015] Thirdly, the present invention provides the use of the above-mentioned silicon-containing conjugated olefin compounds as precursors for drug synthesis.

[0016] The aforementioned silicon-containing conjugated olefin compounds can be used as drug intermediates or drugs themselves, or as important intermediates in organic synthesis, and have certain applications in anti-tumor treatment.

[0017] Fourthly, the present invention provides the use of the above-mentioned silicon-containing conjugated olefin compounds in the preparation of antitumor drugs.

[0018] Preferably, the tumor includes colorectal cancer or cervical cancer.

[0019] This invention utilizes readily prepared allenyl-functionalized silane tetrodes as raw materials to construct a synergistic catalytic system of a metal catalyst and a phosphine ligand. The allenyl-functionalized silane tetrodes, acting as reactants, undergo direct intramolecular reactions within the complex formed by the metal catalyst and the phosphine ligand, yielding the target product in high yield. The catalyst used is a commercially available reagent, and the reaction can be completed with stirring at 40-100 °C. The reaction conditions are mild, the method is simple, and the crude product can be purified to a pure product using rapid silica gel chromatography. Attached Figure Description

[0020] Figure 1 The 1H NMR spectrum of the silicon-containing conjugated olefin compound obtained in Example 3; Figure 2 The image shows the carbon NMR spectrum of the silicon-containing conjugated olefin compound obtained in Example 3. Detailed Implementation

[0021] The present invention will be further described below with reference to specific embodiments, but the present invention is not limited to the following embodiments. Unless otherwise specified, the raw materials used in the embodiments can be commercially available or prepared by conventional methods.

[0022] Example 1: General method for preparing allene-functionalized silicon heterotetram compound 1 S1 (1.0 equivalent), S2 (1.2 equivalent), S3 (1.2 equivalent), CuBr2 (0.4 equivalent), and a solution of 1,4-Dioxane were added to a dry flask equipped with a stir bar and a rubber septum. The mixture was stirred at 70 °C for 21 hours. After completion, the reaction mixture was quenched with saturated NH4Cl solution, extracted with EtOAc, concentrated under vacuum, and the residue was purified by silica gel chromatography to obtain S4.

[0023] S4 (1.0 equivalent), p -TsOH•H2O (0.2 equivalents) and MeOH solution were mixed and stirred overnight at 40 °C. After completion, the mixture was quenched with saturated NaHCO3, extracted with EtOAc, concentrated under vacuum, and the residue was purified by silica gel chromatography to obtain S5.

[0024] S5 (1.1 equivalents), S7 (1.0 equivalents), PPh3 (1.0 equivalents), and a tetrahydrofuran (THF) solution were mixed, and diisopropyl azodicarbonate (DIAD) (1.1 equivalents) was added dropwise with stirring. The reaction mixture was then stirred overnight at room temperature. After completion, the reaction mixture was concentrated under vacuum and purified directly by silica gel rapid chromatography to obtain S6. At 0 ℃ i-PrMgCl•LiCl (1.3 equivalents) was added dropwise to a THF solution of S6 (1.0 equivalents), and the mixture was stirred at 0 °C for 1 hour. Magnesium (1.5 equivalents), 5 mL of a THF solution of S8 (1.0 equivalents), and a grain of iodine were heated to initiate the Grignard reaction. The remaining S6 solution was added dropwise over 1 hour, and the mixture was refluxed for 4 hours, then the reaction mixture was cooled to room temperature. 1-Chloro-1-methylsilane was added dropwise to a solution of the Grignard reagent derived from S6 at 0 °C, and the reaction mixture was heated to room temperature and stirred overnight. The reaction mixture was quenched with saturated NH4Cl solution, extracted with EtOAc, concentrated under vacuum, and the residue was purified by silica gel chromatography to give compound 1.

[0025] In the above synthetic route, R 1 R 2 The definition is as described above.

[0026] Example 2: General method for preparing the compound shown in formula (Ⅰ) Pd(OAc)₂ (2.26 mg, 0.01 mmol, 5.0 mol%) and Ligand 1 (3.32 mg, 0.006 mmol, 6.0 mol%) were added to a dry Schlenk tube equipped with a diaphragm and a magnetic stir bar. The tube was evacuated under high vacuum and refilled with nitrogen (3 times). Toluene (2.0 mL) was introduced into the tube, followed by the dropwise addition of compound 1 (0.2 mmol, 1.0 equivalent, 0.1 M). The reaction tube was stirred at 30 °C for 12 hours. After completion, the solvent was removed under vacuum, and the residue was purified by rapid silica gel chromatography to obtain product I.

[0027] Example 3: Preparation of compound Ia: Compound Ia (24.8 mg, 40% yield) was prepared according to the method in Example 2 and obtained by silica gel column chromatography as a yellow oil. Its 1H and 1C NMR spectra are shown below. Figure 1 and Figure 2 As shown.

[0028] 1 H NMR (400 MHz, CDCl3) d 7.39 – 7.36 (m, 1H), 7.36 – 7.41 (m, 4H), 7.27– 7.2 (m, 2H), 6.98 (s, 1H), 6.91 (t, J = 7.3 Hz, 1H), 6.83 (dd, J= 14.4, 9.0Hz, 1H), 6.71 (d, J = 8.1 Hz, 1H), 5.85 – 5.72 (m, 1H), 5.24 (s, 1H), 5.23 –5.10 (m, 2H), 4.95 – 4.83 (m, 2H), 2.14 – 2.02 (m, 2H), 0.49 (s, 3H). 13 C NMR (100 MHz, CDCl3) d 160.7, 142.9, 138.4, 137.6, 136.5, 136.0, 134.4, 131.5, 129.8, 128.2, 127.8, 122.2, 120.8, 118.5, 115.4, 114.5, 21.9, -4.0. HRMS (ESI) m / z: [M+Na] + Calculated for C 20 H 22 OSi:329.1332, found:329.1337. Example 4: Preparation of compound Ib: Compound Ib (42.3 mg, yield 44%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography as a yellow oil.

[0029] 1 H NMR (400 MHz, CDCl3) d 7.35 (dd, J = 7.4, 1.7 Hz, 1H), 7.25 – 7.20 (m,3H), 7.10 (d, J = 7.9 Hz, 2H), 6.94 (s, 1H), 6.91 – 6.87 (m, 1H), 6.86 – 6.77(m, 1H), 6.69 (dd, J = 8.1, 1.0 Hz, 1H), 5.82 – 5.69 (m, 1H), 5.27 (s, 1H), 5.20 – 5.06 (m, 2H), 4.93 – 4.81 (m, 2H), 2.30 (s, 3H), 2.10 – 2.00 (m, 2H),0.46 (s, 3H). 13C NMR (100 MHz, CDCl3) d 160.7, 143.0, 137.8, 137.4, 136.6, 136.0, 134.7, 134.4, 131.5, 129.8, 128.9, 122.2, 120.7, 118.2, 115.4, 114.5, 21.9, 21.4, -4.0. HRMS (ESI) m / z: [M+Na] + Calculated for C 21 H 24 OSi: 343.1489, found:343.1485. Example 5: Preparation of compound Ic: Compound Ic (35.6 mg, yield 54%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography as a yellow oil.

[0030] 1 H NMR (400 MHz, CDCl3) d 7.32 – 7.28 (m, 1H), 7.26 – 7.21 (m, 2H), 7.20 – 7.15 (m, 1H), 6.94 – 6.89 (m, 2H), 6.86 – 6.81 (m, 2H), 6.74 – 6.67 (m,1H), 6.65 – 6.62 (m, 1H), 5.77 – 5.63 (m, 1H), 5.22 (s, 1H), 5.16 – 5.03 (m,2H), 4.87 – 4.76 (m, 2H), 2.07 – 1.96 (m, 2H), 0.41 (s, 3H). 13 C NMR (100 MHz, CDCl3) d 162.18 (d, J = 247.8 Hz), 160.6, 141.3, 138.4,136.3, 136.1, 134.5, 133.73 (d, J = 3.5 Hz), 131.5, 131.5, 131.4, 122.1, 120.8,118.6, 115.3, 115.3, 115.1, 114.5, 21.8, -4.0. 19F NMR (376 MHz, CDCl3) δ -113.7. HRMS (ESI) m / z: [M+Na] + Calculated for C 20 H 21 FOSi: 347.1238, found347.1235. Example 6: Preparation of compound Id: Compound Id (19.6 mg, yield 27%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography. It was a yellow oily substance.

[0031] 1 H NMR (400 MHz, CDCl3) d 7.40 – 7.35 (m, 3H), 7.32 (d, J = 8.5 Hz, 2H),7.29 – 7.26 (m, 1H), 7.25 – 7.23 (m, 1H), 6.95 – 6.85 (m, 2H), 6.74 (dd, J =8.1, 1.0 Hz, 1H), 5.84 – 5.73 (m, 1H), 5.28 (s, 1H), 5.24 – 5.11 (m, 2H), 4.96 – 4.85 (m, 2H), 2.14 – 2.05 (m, 2H), 1.31 (s, 9H), 0.50 (s, 3H). 13 C NMR (100 MHz, CDCl3) d 160.7, 151.0, 142.9, 137.5, 136.7, 136.0, 134.8, 134.4, 131.5, 129.6, 125.2, 122.2, 120.7, 118.2, 115.5, 114.5, 34.8, 31.4, 21.9, -4.0. HRMS (ESI) m / z: [M+Na] + Calculated for C 24 H 30 OSi: 349.1958, found:349.1962. Example 7: Preparation of compound Ie: Compound Ie (41.4 mg, yield 54%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography as a yellow oil.

[0032] 1 H NMR (400 MHz, CDCl3) d 7.55 – 7.49 (m, 4H), 7.52 – 7.45 (m, 5H), 7.29– 7.25 (m, 1H), 7.21 (td, J = 7.7, 1.8 Hz, 1H), 6.96 (s, 1H), 6.91 – 6.88 (m,1H), 6.87 – 6.81 (m, 1H), 6.67 (dd, J = 7.7, 0.9 Hz, 1H), 5.81 – 5.70 (m, 1H), 5.25 (s, 1H), 5.22 – 5.09 (m, 2H), 4.93 – 4.81 (m, 2H), 2.12 – 2.00 (m, 2H), 0.47 (s, 3H). 13 C NMR (100 MHz, CDCl3) d 160.7, 142.2, 140.7, 140.5, 138.6, 136.6, 136.6, 136.1, 134.5, 131.5, 130.3, 128.95, 128.94, 127.6, 127.2, 126.9, 122.2, 120.8, 118.5, 115.4, 114.5, 21.9, -4.0. HRMS (ESI) m / z: [M+H] + Calculated for C 26 H 26 OSi: 383.1826, found: 383.1820. Example 8: Preparation of compound If: Compound If (28.4 mg, yield 44%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography. It was a yellow oily substance.

[0033] 1 H NMR (400 MHz, CDCl3) d 7.37 (dd, J= 7.3, 1.8 Hz, 1H), 7.25 (td, J = 7.6,1.7 Hz, 1H), 7.21 – 7.17 (m, 1H), 7.15 (d, J = 7.3 Hz, 2H), 7.05 (d, J = 7.4 Hz,1H), 6.96 (s, 1H), 6.91 (td, J = 7.4, 1.0 Hz, 1H), 6.88 – 6.80 (m, 1H), 6.73 –6.69 (m, 1H), 5.83 – 5.71 (m, 1H), 5.25 (s, 1H), 5.23 – 5.09 (m, 2H), 4.95 –4.83 (m, 2H), 2.32 (s, 3H), 2.13 – 2.02 (m, 2H), 0.48 (s, 3H). 13 C NMR (101 MHz, CDCl3) δ 160.7, 143.2, 138.1, 137.8, 137.5, 136.5,136.0, 134.4, 131.5, 130.4, 128.6, 128.1, 126.9, 122.2, 120.8, 118.4, 115.4,114.5, 21.9, 21.5, -4.0. HRMS (ESI) m / z: [M+Na] + Calculated for C 26 H 26 OSi: 343.1489, found: 343.1484. Example 9: Preparation of compound Ig: Compound Ig (28.4 mg, yield 42%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography. It was a yellow oily substance.

[0034] 1 H NMR (400 MHz, CDCl3) d 7.37 (dd, J = 7.3, 1.8 Hz, 1H), 7.25 (td, J= 7.7,1.7 Hz, 1H), 6.96 – 6.88 (m, 5H), 6.87 – 6.81 (m, 1H), 6.72 (dd, J = 8.0, 0.9Hz, 1H), 5.83 – 5.71 (m, 1H), 5.28 (s, 1H), 5.23 – 5.09 (m, 2H), 4.95 – 4.84(m, 2H), 2.28 (s, 6H), 2.12 – 2.03 (m, 2H), 0.48 (s, 3H). 13 C NMR (100 MHz, CDCl3) d 160.7, 143.4, 137.8, 137.5, 136.5, 135.9, 134.4, 131.5, 129.5, 127.5, 122.2, 120.8, 118.3, 115.4, 114.5, 21.9, 21.4, -4.0. HRMS (ESI) m / z: [M+Na] + Calculated for C 22 H 26 OSi: 357.1645, found:357.1642. Example 10: Preparation of compound Ih: Compound Ih (67.5 mg, yield 53%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography. It was a yellow oily substance.

[0035] 1 H NMR (400 MHz, CDCl3) d 7.49 (dd, J = 7.4, 1.7 Hz, 1H), 7.44 – 7.41 (m,1H), 7.35 (td, J = 7.7, 1.7 Hz, 1H), 7.32 – 7.28 (m, 2H), 7.13 (s, 1H), 7.04 –7.00 (m, 1H), 6.98 – 6.93 (m, 1H), 6.82 (d, J= 8.1 Hz, 1H), 5.96 – 5.83 (m,1H), 5.55 (s, 1H), 5.33 – 5.19 (m, 2H), 5.06 – 4.94 (m, 2H), 2.27 – 2.15 (m,2H), 1.41 (s, 18H), 0.6 (s, 3H). 13 C NMR (100 MHz, CDCl3) d 160.8, 150.6, 144.1, 137.4, 137.0, 136.8, 136.0, 134.5, 131.5, 124.2, 122.3, 122.0, 120.7, 117.8, 115.4, 114.4, 35.0, 31.6, 21.9, -4.0. HRMS (ESI) m / z: [M+Na] + Calculated for C 28 H 38 OSi: 441.2584, found:441.2579. Example 11: Preparation of compound Ii: Compound Ii (50.0 mg, yield 55%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography. It was a yellow oily substance.

[0036] 1 H NMR (400 MHz, CDCl3) d 7.27 – 7.22 (m, 4H), 7.20 – 7.15 (m, 1H), 6.98 (dd, J = 8.5, 3.2 Hz, 1H), 6.91 (s, 1H), 6.87 – 6.81 (m, 1H), 6.80 – 6.72 (m,1H), 6.59 (dd, J = 8.8, 4.0 Hz, 1H), 5.77– 5.63 (m, 1H), 5.14 – 5.04 (m, 3H), 4.89 – 4.78 (m, 2H), 2.05 – 1.95 (m, 2H), 0.42 (s, 3H). 13 C NMR (101 MHz, CDCl3) d 157.3 (dd, J= 238.4 Hz), 156.5 (dd, J = 29.0Hz), 143.2, 137.52 (d, J = 23.6 Hz), 136.3, 134.0, 129.8, 128.3, 127.9, 124.33(d, J = 3.7 Hz), 121.52 (d, J = 21.1 Hz), 118.6, 117.9, 117.7, 116.60 (d, J = 7.2Hz), 114.8, 21.6, -4.2. 19 F NMR (376 MHz, CDCl3) d -124.7. HRMS (ESI) m / z: [M+H] + Calculated for C 20 H 21 FOSi: 325.1418, found: 325.1413. Example 12: Preparation of compound Ij: Compound Ij (22.5 mg, yield 36%) was prepared according to the method in Example 2 and obtained by silica gel column chromatography. It was a yellow oily substance.

[0037] 1 H NMR (400 MHz, CDCl3) d 7.27 (dd, J = 7.3, 1.8 Hz, 1H), 7.24 – 7.19 (m,1H), 6.87 (t, J = 7.2 Hz, 1H), 6.74 – 6.65 (m, 2H), 5.93 (d, J = 9.0 Hz, 1H),5.74 – 5.62 (m, 1H), 5.49 – 5.46 (m, 1H), 5.08 – 5.00 (m, 2H), 4.88 – 4.79(m, 2H), 2.64 – 2.52 (m, 1H), 1.99 – 1.89 (m, 2H), 1.71 – 1.59 (m, 5H), 1.29 – 1.21 (m, 2H), 1.13 – 1.06 (m, 2H), 0.36 (s, 3H). 13 C NMR (100 MHz, CDCl3) d 160.9, 153.6, 135.5, 134.7, 134.2, 131.4, 122.1, 120.6, 117.7, 115.6, 114.4, 38.1, 32.7, 32.7, 26.0, 25.8, 21.8, -4.2. HRMS (ESI) m / z: [M+K] + Calculated for C 20 H 28 OSi: 351.1541, found:351.1546. Example 13: Late-stage transformation of the compound shown in (Ⅰa) Under a nitrogen atmosphere, a dry, sealed tubular reactor equipped with a stir bar was charged with Ia (61.22 mg, 0.2 mmol, 1.0 equivalent) in DCM (2.0 mL, 0.1 M) and Grubbs II catalyst (8.48 mg, 0.01 mmol, 5 mol%). The mixture was stirred at 40 °C for 12 hours. Once complete, the reaction solution was concentrated and purified by silica gel column chromatography to give product IIa 47.7 mg in 85% yield as a colorless oil.

[0038] 1 H NMR (400 MHz, CDCl3) d 7.40 (dd, J = 7.3, 1.8 Hz, 1H), 7.34 – 7.30 (m,2H), 7.29 – 7.23 (m, 2H), 7.23 – 7.19 (m, 1H), 7.17 – 7.12 (m, 2H), 6.87 (t, J = 7.2 Hz, 1H), 6.73 – 6.66 (m, 2H), 6.32 – 6.25 (m, 1H), 5.31 (s, 1H), 1.77 –1.70 (m, 1H), 1.63 – 1.56 (m, 1H), 0.52 (s, 3H). 13 C NMR (100 MHz, CDCl3) d161.0, 142.1, 139.2, 138.9, 135.9, 134.8, 134.2, 131.7, 128.8, 128.4, 127.1, 121.4, 1210, 115.3, 17.4, -3.4. HRMS (ESI) m / z: [M+Na]+ calculated for C 18 H 18 OSi: 363.0942, found: 363.0939. Test Example 1: Antitumor activity test of the compound shown in (Ⅰa) The compounds of this invention have good antitumor activity. In this embodiment, compound Ia is used as an example for testing.

[0039] The assay was performed according to the Cell Counting Kit-8 method: a 100 mM Ia stock solution was prepared with DMSO and stored at -20°C for later use. 100 μL of cell suspension was added to each well of a 96-well plate (24 h after drug administration: SW480 cell density: 20,000 cells / well, HeLa cell density: 8,000 cells / well; 72 h after drug administration: SW480 cell density: 6,000 cells / well, HeLa cell density: 3,000 cells / well), and the plates were incubated overnight at 37°C, 5% CO2. After cell attachment, 100 μL of Ia at different concentrations was added to treat SW480 and HeLa cells, respectively. The control group was treated with 100 μL of complete culture medium (DSMO content in the control group was the same as the highest concentration group), and the blank group contained only 100 μL of complete culture medium (cell-free). Each group was configured with 3 replicates. After culturing in a cell culture incubator (37 ℃, 5% CO2) for 72 h, the culture medium was discarded, and 100 μL of 10% CCK-8 solution (Beyotime, C0038) was added. The cells were then incubated at 37 ℃ for 0.5–1 h. Subsequently, the absorbance of the 96-well plate at 450 nm was measured using a microplate reader, and the cell viability and inhibition rate were calculated.

[0040] The experimental results are shown in Table 1 below: Table 1 According to the experimental results, the compound shown in (Ⅰa) has certain anti-tumor activity, and compound Ⅰa can significantly inhibit the proliferation of HeLa cells in a concentration- and time-dependent manner.

[0041] The above description is merely a specific embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.

Claims

1. A silicon-containing conjugated olefin compound, characterized by, The compound has a structural formula as shown in the following formula (I): Among them, R 1 It is hydrogen or halogen; R 2 is cycloalkyl, phenyl or substituted phenyl; the substitution is selected from one of C 1-4 alkyl, aryl or halogen.

2. A process for producing a silicon-containing conjugated olefin compound as claimed in claim 1, characterized by, The preparation method comprises the following steps: The phosphine ligand, the metal palladium catalyst and the solvent are mixed under an inert gas atmosphere, the bis-alkenyl functionalized silatetra compound 1 is added, the solvent is removed under vacuum after the reaction is completed, and the sila conjugated olefin compound is obtained after purification; The synthetic route is shown in the following formula: 。 3. The preparation method according to claim 2, characterized in that, The metal palladium catalyst is palladium acetate.

4. The preparation method according to claim 3, characterized in that, The molar ratio of the bis-alkenyl functionalized silatetra compound 1 and the catalyst is 1:0.03-0.

06.

5. The preparation method according to claim 2, characterized in that, The phosphine ligand is 1,1'-bis(diphenylphosphino) ferrocene.

6. The preparation method according to claim 5, characterized in that, The molar ratio of the bis-alkenyl functionalized silatetra compound 1 and the phosphine ligand is 1:0.01-0.

05.

7. The preparation method according to claim 2, characterized in that, The solvent is 1,4-dioxane.

8. The preparation method according to claim 2, characterized in that, The reaction temperature is 40-100 DEG C, and the reaction time is 10-24 h.

9. The sila conjugated olefin compound according to claim 1 is applied to the preparation of an antitumor drug.

10. Use according to claim 9, characterized in that, The tumor comprises colorectal cancer or cervical cancer.

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