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Novel allyl hydroximic acid derivative containing sulfonate structure as well as preparation method and application of novel allyl hydroximic acid derivative

A technology of propenyl hydroxamic acid and sulfonate ester, which is applied in the direction of sulfonate ester preparation, drug combination, organic chemistry, etc., to achieve the effect of improving biological activity

Pending Publication Date: 2022-07-22
NANJING UNIV
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  • Application Information

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Problems solved by technology

Chinese patent document CN 110590615 A ​​discloses a class of ferulic acid sulfonate derivatives, but the inventor has further studied it and found that the preferred compound in the p-coumaric acid sulfonate derivatives is oxidative to xanthine at a concentration of 10 μM. The inhibition rate of the enzyme is 67.00%, while the preferred compound in the ferulic acid sulfonate derivative only has an inhibition rate of 20.50% to xanthine oxidase at a concentration of 10 μM, which still needs to be further improved

Method used

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  • Novel allyl hydroximic acid derivative containing sulfonate structure as well as preparation method and application of novel allyl hydroximic acid derivative
  • Novel allyl hydroximic acid derivative containing sulfonate structure as well as preparation method and application of novel allyl hydroximic acid derivative
  • Novel allyl hydroximic acid derivative containing sulfonate structure as well as preparation method and application of novel allyl hydroximic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 4-(3-(Hydroxyamino)-3-oxopropyl-1-en-1-yl)phenylbutane-1-sulfonate

[0030]

[0031] It is called spartamin G1.

[0032] Dissolve p-coumaric acid (1 mmol) in a mixed solution of 10 mL of dichloromethane and 1 mL of N,N-dimethylformamide, add n-butylsulfonyl chloride, stir under ice bath conditions for 30-60 min, add dicyclohexyl Carbodiimide (1.5 mmol) and 4-dimethylaminopyridine (0.5 mmol) were moved to room temperature and stirred for 4-12 h, followed by thin layer chromatography. After the reaction, the precipitate was filtered, and the filtrate was extracted with ethyl acetate , washed with saturated sodium chloride solution, distilled off the organic solvent under reduced pressure, recrystallized with a mixed solvent of N,N-dimethylformamide and ethanol, and the obtained compound was dissolved in a mixed solution of 10 mL of isopropanol and 1 mL of piperidine, Hydroxylamine hydrochloride (1 mmol) was added, stirred for 4-8 h under ice bath conditions, the organ...

Embodiment 2

[0035] 4-(3-(Hydroxyamino)-3-oxopropyl-1-en-1-yl)-2-methoxyphenylbutane-1-sulfonate

[0036]

[0037] It is called Spartina G2.

[0038] The preparation method refers to Example 1, the initial raw material of the reaction is ferulic acid, and the sulfonyl chloride is n-butylsulfonyl chloride.

[0039] The final product is a white powder, the yield is 37.1%, the melting point is 109-110°C, 1 H NMR (600MHz, DMSO-d 6 )δ10.79(s,1H,-OH),9.09(s,1H,-NH-),7.47(d,J=15.8Hz,1H,=CH-),7.40(s,1H,-ArH), 7.31(d,J=8.3Hz,1H,-ArH),7.20(d,J=8.2Hz,1H,-ArH),6.51(d,J=15.8Hz,1H,-CO-CH=),3.89( s,3H,-OCH3 ),3.54-3.44(m,2H,-CH 2 -),1.84-1.79(m,2H,-CH 2 -),1.48-1.42(m,2H,-CH 2 -),0.92(t,J=7.4Hz,3H,-CH 3 ). 13 C NMR (151MHz, DMSO-d 6 )δ162.98,152.01,138.76,137.85,135.45,124.72,120.69,120.33,112.88,56.49,51.04,25.70,21.14,13.87.HRMS(ESI-TOF)m / z:[M+H] + Calcd.for C 14 H 20 NO 6 S 330.1011, Found 330.1010.

Embodiment 3

[0041] 4-(3-(Hydroxyamino)-3-oxopropyl-1-en-1-yl)-2-methoxyphenyl-4-chlorobenzenesulfonate

[0042]

[0043] It is called Spartina G3.

[0044] The preparation method refers to Example 1, the initial raw material of the reaction is ferulic acid, and the sulfonyl chloride is 4-chlorobenzenesulfonyl chloride.

[0045] The final product was a white powder with a yield of 35.8% and a melting point of 148-149°C. 1 H NMR (600MHz, DMSO-d 6 )δ10.80(s,1H,-OH),9.10(s,1H,-NH-),7.86-7.84(m,2H,-ArH),7.75(d,J=8.7Hz,2H,-ArH) ,7.44(d,J=15.8Hz,1H,=CH-),7.28(s,1H,-ArH),7.18(s,2H,-ArH),6.49(d,J=15.8Hz,1H,-CO -CH=),3.55(s,3H,-CH 3 ). 13 C NMR (151MHz, DMSO-d 6 )δ162.92,151.76,140.39,138.26,137.68,135.94,134.25,130.62,130.07,124.46,120.99,120.29,112.82,56.05.HRMS(ESI-TOF)m / z:[M+H] + Calcd.for C 16 H 15 ClNO 6 S 384.0308, Found 384.0311.

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Abstract

The invention discloses a benzene propenyl hydroximic acid derivative containing a sulfonate structure as well as a preparation method and application of the benzene propenyl hydroximic acid derivative. According to the source and the effect in spartina alterniflora resource utilization, the spartina alterniflora is named as spartina alterniflora G series. The structural formula of the benzene allyl hydroximic acid derivative containing the sulfonate structure is shown as a formula (I), wherein R1 is selected from-H or C1-C6 alkoxy, and R2 is selected from C1-C6 alkyl and substituted or non-substituted phenyl. The compound provided by the invention has xanthine oxidase inhibitory activity, and can be used for preparing drugs for treating and / or preventing hyperuricemia. The upstream preparation raw materials p-coumaric acid and ferulic acid of the compound can be obtained by a natural extraction method, and resource utilization of spartina alterniflora can be realized.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a class of phenylpropenyl hydroxamic acid derivatives containing a sulfonate structure and a preparation method and application thereof. Background technique [0002] Hydroxybenzene acrylic derivatives have a variety of biological functions, such as scavenging free radicals and regulating human body functions. Among them, p-coumaric acid and ferulic acid are distributed in a variety of plants and belong to natural medicinal molecules. In order to reduce the environmental pollution caused by chemical synthesis methods, natural extraction is also an important means to obtain such pharmaceutical intermediates, but the large-scale development of related plants has not yet been achieved. [0003] Spartina alterniflora is widely distributed in coastal tidal flats, and has high content of natural products such as coumaric acid and ferulic acid. Invasion biology ...

Claims

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Application Information

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IPC IPC(8): C07C309/65C07C309/73C07C303/30A61P19/06A61P19/02A61P9/04
CPCC07C309/65C07C309/73A61P19/06A61P19/02A61P9/04
Inventor 焦庆才刘均忠杨雨顺钦佩王斌
Owner NANJING UNIV
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