Pentacyclic thiazole indolone piperazine amide derivative and application thereof

By synthesizing pentacyclic thiazole indole piperazine amide derivatives, the problem of insufficient targeting and inhibitory activity of existing antitumor drugs in cancer treatment has been solved, and significant inhibitory effects on HeLa cervical cancer, HT-29 human colon cancer and HGC-27 human gastric cancer cells have been achieved.

CN122444757APending Publication Date: 2026-07-24XINJIANG INST OF ENG
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Patent Information

Application Number
CN202610625338.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2026-05-08
Publication Date
2026-07-24

AI Technical Summary

Technical Problem

Existing anti-tumor drugs lack efficient targeting and significant inhibitory activity when treating cancer, making it difficult to effectively inhibit the growth of HeLa cervical cancer, HT-29 human colon cancer, and HGC-27 human gastric cancer cells.

Method used

The synthesis of pentacyclic thiazole indole-piperazine amide derivatives was carried out using ethyl cyanoacetate as the starting material. Different substituents were introduced through a series of chemical reactions to generate compounds I1-I28. The specific steps included hydroxylation, reduction, esterification, bromination, pyridinoid reaction and deBoc treatment, and finally reaction with acyl chloride to form compounds with different substituted structures.

Benefits of technology

Compounds I14, I21, I27, and I28 showed significant inhibitory activity against HeLa cervical cancer cells, compounds I9, I11, I14, and I21 showed significant inhibitory activity against HT-29 human colon cancer cells, and compounds I1-I28 showed significant inhibitory effects against HGC-27 human gastric cancer cells, demonstrating significant antitumor activity.

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Abstract

The invention relates to a pentacyclic thiazole indolone piperazine amide derivative and application thereof. According to the derivative, ethyl cyanoacetate is used as a starting raw material, and a hydroxylamine compound (A) is generated under the action of sodium nitrite and phosphoric acid; 2-amino ethyl cyanoacetate (B) is obtained through reduction and sequentially reacts with acetic anhydride and a Lawson reagent, and a 5-amino-4-formate thiazole compound (D) is obtained; the preparation method comprises the following steps: carrying out NBS bromination on 2-bromo-6, 7-dihydrothiazolo [5 '', 4'': 4 ', 5'] pyrimido [1 ', 2': 1, 2] pyridino [3, 4-b] indole-4 (12H)-one under the catalysis of phosphorus oxychloride to generate 2-bromo-6, 7-dihydrothiazolo [5 '', 4'': 4 ', 5'] pyrimido [1 ', 2': 1, 2] pyridino [3, 4-b] indole-4 (12H)-one (F), carrying out a reaction with Boc piperazine under an alkaline condition, and carrying out Boc removal treatment to obtain a compound (H); and finally, reacting with acyl chloride to synthesize 28 pentacyclic thiazole indolone piperazine amide compounds (I1-I28) with different substitution structures. The 28 compounds are used for experiments on three cancer cells, and results show that the 28 compounds have remarkable inhibitory activity on Hela cervical cancer cells, HT-29 human colon cancer cells and HGC-27 human gastric cancer cells.
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