Cinnamoyl sulfonamide compound preparation and applications of cinnamoyl sulfonamide compounds in anti-tumor treatment drugs

A technology of cinnamoyl sulfonamides and compounds, which is applied in the preparation of cinnamoyl sulfonamide compounds and their application in anticancer drugs, and can solve the problems of sulfonamide biological activity, low cytotoxicity, etc.

Inactive Publication Date: 2012-12-26
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Meanwhile, previous reports indicated that sulfonamides have potential bioactivity and low cytotoxicity

Method used

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  • Cinnamoyl sulfonamide compound preparation and applications of cinnamoyl sulfonamide compounds in anti-tumor treatment drugs
  • Cinnamoyl sulfonamide compound preparation and applications of cinnamoyl sulfonamide compounds in anti-tumor treatment drugs
  • Cinnamoyl sulfonamide compound preparation and applications of cinnamoyl sulfonamide compounds in anti-tumor treatment drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1: Preparation of N-(p-fluorobenzenesulfonyl)cinnamide (compound 9c)

[0016]

[0017] In a 100ml one-necked flask, dissolve benzaldehyde (10mmol) and malonic acid (12.1mmol) in 30ml of pyridine respectively, stir magnetically and heat to 80-90°C, add piperidine (1.21mmol) dropwise and continue heating and stirring for 24h (TLC detects the degree of progress of the reaction). After the reaction was completed, the solvent was dried with a vacuum pump, and the residual solid was washed with 10% hydrochloric acid. After fully mashing, filter with suction and wash with a large amount of water, and finally wash with n-hexane for 3 times, and dry to obtain the product cinnamic acid. The product was purified, after drying, weighed 2g and added it to another 100ml single-necked flask, added an equimolar amount of p-fluorobenzenesulfonamide, and added 2.2 times the molar amount of EDCI and DMAP, and used 20ml CH 2 Cl 2 Dissolve, and react with magnetic stirring at ...

Embodiment 2

[0018] Example 2: Preparation of N-(p-bromobenzenesulfonyl)cinnamide (compound 9e)

[0019]

[0020] The preparation method is the same as in Example 1. Replace p-fluorobenzenesulfonamide in Example 1 with p-bromobenzenesulfonamide. The target compound was obtained as colorless crystals. Yield 90%; m.p.166-167℃. 1 H NMR (300MHz, CDCl 3 ): δ6.39 (d, J=15.57Hz, 1H), 7.35-7.42 (m, 3H), 7.44-7.50 (m, 2H, ArH), 7.67-7.72 (dd, J 1 = 3.3Hz,J 2 =12.06Hz, 3H, ArH), 8.00 (d, J=8.79Hz, 2H, ArH), 8.49 (s, 1H, NH).ESI-MS: 365.97 (C 15 h 13 BrNO 3 S, [M+H] + ).Anal.Calcd for C 15 h 12 BrNO 3 S: C, 49.19; H, 3.30; N, 3.82%. Found: C, 49.35; H, 3.46; N, 3.92%.

Embodiment 3

[0021] Example 3: Preparation of (E)-3-(4-fluorophenyl)-N-(benzenesulfonyl)acrylamide (compound 10a)

[0022]

[0023] The preparation method is the same as in Example 1. Replace the benzaldehyde in the example one with p-fluorobenzaldehyde, and replace the p-fluorobenzenesulfonamide in the example one with benzenesulfonamide. The target compound was obtained as pale yellow crystals. Yield 82%; m.p.165-166℃. 1 H NMR (300MHz, CDCl 3 ): δ6.34 (d, J=15.54Hz, 1H), 7.04-7.10 (m, 2H, ArH), 7.45-7.50 (m, 2H), 7.54-7.57 (m, 2H, ArH), 7.59-7.68 (m, 2H, ArH), 8.10-8.17 (m, 3H).ESI-MS: 306.05 (C 15 h 13 FNO 3 S, [M+H] + ).Anal.Calcd for C 15 h 12 FNO 3 S: C, 59.01; H, 3.96; N, 4.59%. Found: C, 59.23; H, 4.23; N, 4.75%.

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Abstract

The invention relates to a class of cinnamoyl sulfonamide derivatives, wherein the derivatives are characterized in that the derivatives have the following general formula, and R1 in the structural formula is represented in the picture. The cinnamic acid derivatives of the present invention have effects of tubulin polymerization resistance and mice melanoma cell B16-F10 proliferation inhibition, such that the cinnamic acid derivatives of the present invention can be adopted as potential anti-tumor drugs. The present invention further discloses a production method for the derivatives.

Description

technical field [0001] The invention relates to cinnamoylsulfonamide compounds, a preparation method thereof and antitumor drugs. Background technique [0002] Uncontrolled cell replication is an important factor in the occurrence of cancer. In the process of cell replication, the microcosm - the most important cytoskeleton - also plays an important role in cell activities. Microtubules have the function of pulling chromosomes in the process of cell mitosis. At the same time, under normal conditions, microtubules are in the dynamic balance of microscopic protein dimers. Disruption of the balance can result in preventing the normal progression of the cell cycle and causing apoptosis. Microscopic proteins are therefore the most important targets for cancer chemotherapy. [0003] Studies have found that some small molecules can bind microscopic proteins, affect microscopic aggregation or depolymerization, thereby preventing cell cycle and leading to apoptosis. Colchicine is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/51C07C303/40A61K31/18A61P35/00
Inventor 朱海亮骆银裘科明
Owner NANJING UNIV
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