Diphyllin thiazole derivative as well as preparation method and application thereof

By preparing non-glycoside structure yaminothiazole derivatives, the problem of poor metabolic stability of yaminothiazole derivatives is solved, and the tumor cell proliferation inhibitory activity is improved. It is suitable for drug development for the treatment of liver cancer, colorectal cancer and lung cancer.

CN119874696AActive Publication Date: 2025-04-25NANTONG UNIV
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Patent Information

Application Number
CN202510077560.5
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-01-17
Publication Date
2025-04-25
Estimated Expiration
2045-01-17

AI Technical Summary

Technical Problem

The metabolic stability of existing yamlosin glycoside derivatives is poor, it is difficult to effectively inhibit tumor cell proliferation, and the chemical synthesis is complex.

Method used

The non-glycoside structure of yamellin thiazole derivative was designed and synthesized. The yamellin was converted into thiazole derivatives through a series of organic reactions, avoiding the easy hydrolyzed glycosidic bonds. The yamellin was coupled and bromine reaction with trifluoromethanesulfonic anhydride, triethylamine, tributyl (1-ethoxyethylene)tin, 1,1'-bisdiphenylphosphine ferrocene palladium dichloride, PyHBr3 and thioacetamide and other reagents were used to perform coupling and bromine reactions to prepare yamellin thiazole derivatives with stability better than glycoside compounds.

Benefits of technology

The metabolic stability of yamlosin thiazole derivatives has been improved, and tumor cell proliferation inhibitory activity comparable to or better than paclitaxel is shown. It is suitable for drug development for the treatment of liver cancer, colorectal cancer and lung cancer.

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Abstract

The invention belongs to the technical field of medicinal chemistry and pharmacology, and discloses a diphyllin thiazole derivative as well as a preparation method and application thereof. The structure of the diphyllin thiazole derivative is shown in the following formula: # imgabs0 #, wherein R represents one of methyl, amino, anilino, tertiary butyl, ethyl, isopropyl, ethoxycarbonyl, cyclopropyl, methylamino, butylamino, acetamido and hydrazino. The preparation method comprises the following steps: reacting diphyllin with trifluoromethanesulfonic anhydride and triethylamine to obtain diphyllin trifluoromethanesulfonate; the preparation method comprises the following steps: carrying out stile coupling reaction on diphyllin trifluoromethanesulfonate, tributyl (1-ethoxyethylene) tin and 1, 1 '-bis (diphenylphosphine) ferrocene palladium dichloride, so as to obtain a diphyllin ketone derivative; carrying out bromination reaction on the diphyllin derivative and PyHBr3 to obtain a brominated derivative; and reacting the brominated derivative with a thioacetamide derivative to obtain the diphyllin thiazole derivative. The diphyllin thiazole derivative is relatively high in tumor cell proliferation inhibition activity and good in metabolic stability.
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Citation Information

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