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3-4'-5-trihydroxystilbene nitroethylene compound as well as preparation method and application thereof

A technology of resveratrol and nitroethylene, applied in the field of resveratrol nitroethylene compounds and preparation thereof, can solve the problems of poor selectivity, low bioavailability, poor water solubility of resveratrol, etc. Inhibitory effect

Inactive Publication Date: 2019-07-23
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, resveratrol has poor water solubility, low bioavailability, low relative activity, and poor selectivity. A large number of researchers have used the structure of resveratrol as the mother nucleus to modify it in order to obtain lead compounds with higher activity.

Method used

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  • 3-4'-5-trihydroxystilbene nitroethylene compound as well as preparation method and application thereof
  • 3-4'-5-trihydroxystilbene nitroethylene compound as well as preparation method and application thereof
  • 3-4'-5-trihydroxystilbene nitroethylene compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 1,5-dimethoxy-3-((E)-4-(methoxy)styryl)-2-(E)-nitrovinyl)benzene (compound 1)

[0030]

[0031] Weigh pterostilbene A (1.28g, 5mmol) and dissolve it in a 100mL round bottom flask with acetone, add anhydrous potassium carbonate (1.38g, 6mmol), tetrabutylammonium bromide (1.94g, 6mmol), methyl bromide (380uL , 6mmol), reflux reaction, TLC plate to monitor the reaction process, after the completion of the reaction, remove potassium carbonate by suction filtration, vacuum concentration, column chromatography separation (ethyl acetate:petroleum ether=1:5), to obtain white solid B.

[0032] Weigh B (811mg, 3mmol) and dissolve it in a 100mL round bottom flask with acetonitrile, add N,N-dimethylformamide (DMF, 458μL), then slowly add phosphorus oxychloride (280μL, 3mmol); dropwise After completion, return to room temperature for reaction, stir for 1 hour, and stop immediately after the reaction of the system is complete. Take a 1000mL beaker, add 500mL ice wa...

Embodiment 2

[0035] Preparation of 1,5-dimethoxy-3-((E)-4-(ethoxy)styryl)-2-(E)-nitrovinyl)benzene (compound 2)

[0036]

[0037] The preparation method is the same as in Example 1. Substituting ethyl bromide for methyl bromide, the title compound was obtained as a yellow solid powder with a yield of 91% and a melting point of 149-153°C. 1 H NMR (600MHz, DMSO-d 6)δ8.31(d, J=13.3Hz, 1H), 7.89(d, J=13.2Hz, 1H), 7.58(d, J=8.6Hz, 2H), 7.41(dd, J=16.1, 7.9Hz, 1H), 7.05(d, J=16.0Hz, 1H), 6.95(d, J=8.6Hz, 2H), 6.85(d, J=1.9Hz, 1H), 6.63(s, 1H), 4.04(q, J=6.9Hz, 2H), 3.94(d, J=5.3Hz, 3H), 3.89(s, 3H), 1.32(t, J=7.0Hz, 3H). 13 C NMR (151MHz, CDCl 3 (C 20 h 22 NO 5 ,[M+H] + ).

Embodiment 3

[0039] Preparation of 1,5-dimethoxy-2-((E)-2-nitrovinyl)-3-((E)-4-(propoxy)styryl)benzene (compound 3)

[0040]

[0041] The preparation method is the same as in Example 1. Propane bromide was used instead of methyl bromide to obtain the target compound as a yellow solid powder with a yield of 91% and a melting point of 100-102°C. 1 H NMR (600MHz, CDCl 3 )δ8.40(d, J=13.3Hz, 1H), 7.91(d, J=13.3Hz, 1H), 7.46(d, J=8.1Hz, 2H), 7.25(d, J=16.0Hz, 1H) ,6.94-6.88(m,3H),6.72(s,1H),6.42(s,1H),3.96(t,J=6.5Hz,2H),3.93(s,3H),3.90(s,3H), 1.86-1.79(m,2H),1.06(t,J=7.4Hz,3H). 13 C NMR (151MHz, CDCl 3 )δ165.89,136.95,135.15,130.90,125.89,117.55,107.18,100.22,72.30,58.42,58.21,32.32,25.20,13.12.MS(ESI):392.1648.(C 21 h 23 NO 5 ,[M+Na] + ).

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Abstract

The invention discloses a 3-4'-5-trihydroxystilbene nitroethylene compound as well as a preparation method and application thereof, and relates to the technical field of drug design and synthesis. The3-4'-5-trihydroxystilbene nitroethylene compound has the following general formula (the formula is shown in the description). According to the 3-4'-5-trihydroxystilbene nitroethylene compound as wellas the preparation method and application thereof, the 3-4'-5-trihydroxystilbene nitroethylene compound is designed and prepared, and the prepared 3-4'-5-trihydroxystilbene nitroethylene compound isapplied to the preparation of anti-cancer drugs; the results of biological activity tests show that the 3-4'-5-trihydroxystilbene nitroethylene compound has good inhibiting activity on a human gastriccancer cell line MGC 803, a human liver cancer cell line SMMC-7721 and a human breast cancer cell line MDA-MB-231, and thus, the preparation of the 3-4'-5-trihydroxystilbene nitroethylene compound isof great significance for screening out novel anti-cancer drugs.

Description

[0001] Technical field: [0002] The invention relates to the technical field of drug design and synthesis, in particular to a resveratrol nitroethylene compound and its preparation method and application. [0003] Background technique: [0004] Microtubules are hollow tubular structures composed of tubulin and microtubule accessory proteins. Tubulin includes α and β subunits, and microtubule accessory proteins include MAP protein family, Tau protein, and microtubule plus-end tracking protein, etc. Microtubules are one of the main components of the cytoskeleton. They exist in almost all eukaryotic cells and play an important role in maintaining cell shape, transporting intracellular substances, cell division and differentiation. In recent years, studies have found that the abnormal expression of the composition and depolymerization of microtubules affects the process of cell mitosis, and the abnormal expression of proteins causes the imbalance of the dynamic system of microtub...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/32C07C201/12C07C43/215C07C41/16C07C47/575C07C45/00A61P35/00
CPCA61P35/00C07C41/16C07C45/00C07C201/12C07C205/32C07C2601/02C07C2601/14C07C43/215C07C47/575
Inventor 阮班锋郭伟云李遥葛为为
Owner HEFEI UNIV OF TECH
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