Carbazole derivative, preparation method thereof, and application of carbazole derivative serving as anticancer drug

A technology of carbazole derivatives and compounds, which is applied in the field of medicine and chemical industry, can solve the problems of less development and research of carbazole derivatives, and achieve the effects of low normal cell toxicity, good inhibitory activity, and tumor inhibition

Inactive Publication Date: 2014-01-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been patents on carbazole compounds as drugs for the treatment of cancer, but there is still very little research on the development of carbazole derivatives

Method used

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  • Carbazole derivative, preparation method thereof, and application of carbazole derivative serving as anticancer drug
  • Carbazole derivative, preparation method thereof, and application of carbazole derivative serving as anticancer drug
  • Carbazole derivative, preparation method thereof, and application of carbazole derivative serving as anticancer drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment one: the synthesis of compound C-1

[0031] Dissolve 35g of copper nitrate in a mixture of 96ml of acetic acid and 145ml of acetic anhydride, slowly add 20g of carbazole over 10min under an ice bath, and stir at room temperature for 0.5 hours. Then react at 90° C. for 0.5 h, cool down, pour the reaction solution into water, stir continuously, filter with suction, and wash with water to obtain a yellow solid. The filter cake was added to cold 100gKOH and 1500ml ethanol: water 1:1 mixed solution, stirred for 0.5h, filtered, the filtrate was acidified with concentrated hydrochloric acid, and a yellow solid was precipitated, filtered with suction, washed with water, dried, and subjected to silica gel column chromatography (petroleum enzyme / ethyl acetate), to obtain pale yellow solid powder C-1.

[0032] Yield: 70%; 1 H NMR (400MHz, DMSO) δ12.69(s, 1H), 9.50(d, J=2.1Hz, 1H), 8.40(dd, J=9.0, 2.1Hz, 1H), 7.77(d, J=9.0Hz , 1H); ESI-MS m / z: 258[M+H] + .

[0033]...

Embodiment 2

[0035] Embodiment two: the synthesis of compound C-2

[0036] Dissolve 2gC-1 in 30ml concentrated sulfuric acid, then raise the temperature to 90°C, slowly add bromine into the reaction solution, react for 2h, stop the reaction, cool, pour into water, filter, wait for yellow solid, silica gel column chromatography (petroleum ether / acetone) to give C-2 as a pale yellow solid.

[0037] Yield: 50%; 1H NMR (400MHz, DMSO) δ12.72(s, 1H), 9.49(d, J=2.1Hz, 2H), 8.54(d, J=2.1Hz, 2H); ESI-MS m / z:416[M+H] + .

[0038]

[0039] Compound C-2

Embodiment 3

[0040] Embodiment three: the synthesis of compound C-3

[0041] Dissolve 2g of compound C-2 in 30ml of NMP, add 1g of pyrazole, 100mg of Cu 2 O, 200°C, reacted for 24h, cooled, poured the reaction solution into water, stirred continuously, precipitated solid, filtered to obtain a yellow solid, alumina column chromatography (dichloromethane) to obtain a yellow solid C-3.

[0042] Yield: 35%; H NMR (400MHz, DMSO) δ12.83(s, 1H), 9.35(d, J=1.8Hz, 2H), 9.02(d, J=2.6Hz, 2H), 8.76(d, J=1.9Hz, 2H), 8.01(d, J=1.7Hz, 2H), 6.72-6.74(m, 2H).ESI-MS m / z: 390[M+H] + .

[0043]

[0044] Compound C-3

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Abstract

The invention belongs to the fields of medicament and chemical industry, and discloses a carbazole derivative, a preparation method of the carbazole derivative, and an application of the carbazole derivative serving as an anticancer drug. The structural formula of the carbazole derivative is shown in the specification, wherein R1 is piperidyl, morpholinyl, piperazinyl or Bielin group; n is 1, 2 or 3; and R2 is pyrazolyl or pyridyl. At the same time, the invention discloses a preparation method of the carbazole derivative and an application of the carbazole derivative serving as the anticancer drug. The carbazole derivative has strong inhibiting action on the expression of telomere DNA (deoxyribonucleic acid) and DNA of c-myc and other proto-oncogene, has significant inhibiting action on multiple cancer cell strains, has low toxicity to normal cells, and has broad application space in preparation of anticancer drugs.

Description

technical field [0001] The invention belongs to the fields of medicine and chemical industry, and relates to a carbazole derivative, a preparation method thereof, and an application thereof in the preparation of anticancer drugs. Background technique [0002] Cancer is a major disease that threatens human health and life safety. According to statistics, there are about 4 million new cancer patients in the world every year. The research and development of anticancer drugs has always been a hot spot for chemists and pharmacologists. Finding anticancer drugs with high efficiency, high selectivity and less toxic side effects is one of the important directions of drug research and development. Designing and synthesizing anticancer drugs with DNA as the target, especially designing and synthesizing small molecule inhibitors targeting the special advanced structure of telomeric DNA and proto-oncogene DNA, which have important physiological significance, is an important direction f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C07D401/14A61K31/444A61K31/5377A61K31/4155A61K31/4545A61P35/00A61P11/00A61P15/14
Inventor 黄志纾古练权陈维佳谭嘉恒
Owner SUN YAT SEN UNIV
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