高等萜类化合物的合成转化。含18- no - labdatri烯脲的合成及细胞毒性研究

IF 1.1 4区化学 Q4 CHEMISTRY, MEDICINAL

Chemistry of Natural Compounds Pub Date : 2026-08-11 DOI:10.1007/s10600-026-05055-4

Yu. V. Kharitonov, V. I. Antipova, M. K. Marenina, Yu. V. Meshkova, T. G. Tolstikova, E. E. Shults

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引用次数: 0

摘要

以4-异氰酸酯-18-去兰伯酸为原料，以氨、伯胺、仲胺、氨基酸和苯胺为原料，合成了一系列4-脲基-18-去兰伯酸-15,16-环氧-8(17),13,14-labdatrienes。反应在温和的条件下进行，目标产物收率高。合成的化合物对培养的人肿瘤细胞MCF-7和HEK293T以及成纤维细胞hTERT-BJ1的细胞毒性（MTT法）进行了评估。采用层次聚类法对结构-细胞毒性关系进行定性分析，揭示了取代基性质对细胞毒性和选择性影响的几种模式。3、5e和11b对肿瘤细胞的选择性最高（SI = 2.2 ~ 2.3）。

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Synthetic Transformations of Higher Terpenoids. 48. Synthesis and Cytotoxic Properties of 18-Nor-Labdatriene-Containing Ureas

A series of 4-ureido-18-nor-15,16-epoxy-8(17),13,14-labdatrienes were synthesized by the reaction of 4-isocyanato-18-nor-lambertianic acid with ammonia, primary and secondary amines, amino acids, and phenylamines. The reactions occurred under mild conditions with high yields of the target products. The cytotoxicity of the synthesized compounds was assessed against cultivated human tumor cells MCF-7 and HEK293T and fibroblasts hTERT-BJ1 (MTT assay). Hierarchical clustering was used for qualitative analysis of the structure–cytotoxicity relationship and revealed several patterns for the effect of the substituent nature on the cytotoxicity and selectivity. The highest selectivity against tumor cells (SI = 2.2–2.3) was found for 3, 5e, and 11b.

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来源期刊

Chemistry of Natural Compounds 化学-有机化学

CiteScore

1.40

自引率

25.00%

发文量

265

审稿时长

7.8 months

期刊介绍： Chemistry of Natural Compounds publishes reviews and general articles about the structure of different classes of natural compounds, the chemical characteristics of botanical families, genus, and species, to establish the comparative laws and connection between physiological activity and the structure of substances.