3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone and application of the 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone in preparing antitumour drugs

A phenyl, pharmaceutical technology, applied in the direction of antineoplastic drugs, drug combinations, pharmaceutical formulations, etc., to achieve the effect of high efficiency, short time, simple separation and purification

Active Publication Date: 2011-08-17
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no literature reports on the synthesis of 3,5-(E)-dibenzylidene-N-cyclopro

Method used

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  • 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone and application of the 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone in preparing antitumour drugs
  • 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone and application of the 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone in preparing antitumour drugs
  • 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone and application of the 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone in preparing antitumour drugs

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0030] Example 1: When the aromatic aldehyde is 2,4,5-trimethoxybenzaldehyde, 3,5-(E)-bis(2,4,5-trimethoxybenzylidene)-N-ring is prepared Propylpiperidin-4-one (compound 1), orange-red powder, yield 60%, mp150~153°C, ESI-MS: 496.3(M+1); 1 H-NMR(CDCl 3 , Ppm) δ: 8.02 (2H, s, -CH =), 6.82 (2H, s, Ar-H), 6.55 (2H, s, Ar-H), 4.63 (4H, s, -CH 2 -), 3.86 (18H, s, -OCH 3 ), 1.93(s, 1H, -N-CH(CH 2 ) 2 ), 0.44-0.39(m, 4H, -CH(CH 2 ) 2 ).δ: 87.99, 154.18, 151.13, 142.54, 131.93, 116.36, 114.32, 109.17, 97.27, 56.86, 56.35, 56.21, 55.19, 37.42, 6.67

Example Embodiment

[0031] Example 2: When the aromatic aldehyde is 2-fluorobenzaldehyde, 3,5-(E)-bis(2-fluorobenzylidene)-N-cyclopropylpiperidin-4-one (compound 2) is prepared , Is light yellow powder, yield 88%, mp169~172℃, ESI-MS: 352.3(M+1); 1 H-NMR(CDCl 3 , Ppm) δ: 7.88 (2H, s, -CH=), 7.39-7.31 (4H, m, Ph-H), 7.22-7.11 (4H, m, Ph-H), 3.86 (s, 4H, -CH 2 -), 1.90(s, 1H, -N-CH(CH 2 ) 2 ), 0.47-0.40(m, 4H, -CH(CH 2 ) 2 ). 13 C-NMR(100MHz, CDCl 3 , Ppm) δ: 186.71, 162.22, 159.72, 135.09, 130.76, 129.25, 123.99, 123.25, 115.82, 54.98, 37.70, 6.77.

Example Embodiment

[0032] Example 3: When the aromatic aldehyde is 3,4-dimethoxybenzaldehyde, 3,5-(E)-bis(3,4-dimethoxybenzylidene)-N-cyclopropyl is prepared Piperidin-4-one (Compound 3), yellow powder, yield 66%, mp195~198°C, ESI-MS: 436.3(M+1); 1 H-NMR(CDCl 3 , Ppm) δ: 7.75 (2H, s, -CH =), 7.06 (2H, d, J = 8 Hz, Ar-H), 6.97 (2H, s, Ar-H), 6.93 (2H, d, J = 8Hz, Ar-H), 4.01(4H, s, -CH 2 -), 3.92 (12H, s, -OCH 3 ), 1.97(s, 1H, -N-CH(CH 2 ) 2 ), 0.53-0.48(m, 4H, -CH(CH 2 ) 2 ). 13 C-NMR(100MHz, CDCl 3 , Ppm) δ: 187.16, 150.01, 148.86, 136.26, 128.40, 124.04, 123.89, 114.04, 111.13, 55.99, 55.75, 55.12, 37.90, 6.73

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Abstract

The invention discloses 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone and application of the 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone in preparing antitumor drugs. The 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone compound can be obtained by Claisen-Schimidt reaction of aromatic aldehyde and N-cyclopropyl-4-piperidine ketone. The 3,5-(E)-dibenzylidene-N-cyclopropyl piperidine-4-ketone compound can obviously restrain the proliferation of various tumor cells and can be used for preparing drugs for treating leukocythemia, colorectal cancer, lover cancer, skin cancer, gastric cancer, breast cancer, prostatic cancer or other malignant tumor.

Description

Technical field: [0001] The present invention relates to the synthesis of anti-tumor drugs and their preparation methods, in particular to the synthesis of 3,5-(E)-dibenzylidene-N-cyclopropylpiperidin-4-one compounds and their application in the preparation of anti-tumor drugs . Background technique: [0002] Using 4-piperidone as an intermediate and condensing aromatic aldehydes to obtain a series of compounds with anti-tumor, anti-inflammatory, antibacterial and other activities, the representative compound EF-24 (structural formula is as follows) has good anti-tumor activity in vivo and in vitro [Documentation 1，2 ]. However, there is no literature report on the synthesis of 3,5-(E)-dibenzylidene-N-cyclopropylpiperidin-4-one compounds and their application in the preparation of antitumor drugs. [0003] [0004] Chemical structural formula of EF-24 [0005] references [0006] 1. Subramaniam D, May R, Sureban SM, et al. Diphenyl difluoroketone: a curcumin derivativ...

Claims

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Application Information

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IPC IPC(8): C07D213/68C07D405/14C07D401/14A61K31/4412A61K31/443A61K31/444A61K31/4439A61P35/00A61P35/02
Inventor 刘洋许建华黄秀旺刘锋吴梅花
Owner FUJIAN MEDICAL UNIV
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