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Ultrasound-promoted two-step synthesis of 3-arylselenylindoles and 3-arylthioindoles as novel combretastatin A-4 analogues.

ABSTRACT: A series of 3-(3'-hydroxy-4'-methoxyphenyl)selenyl-5,6,7-trimethoxy-1H-indoles and 3-(3'-hydroxy-4'-methoxyphenyl)thio-5,6,7-trimethoxy-1H-indoles were obtained as a new class of combretastatin A-4 (CA-4) analogues via a convenient ultrasound (US)-assisted two-step process involving 3-selenenylation/sulfenylation followed by O-deallylation. With the assistance of US irradiation, both the reaction rates and yields of selenenylation, sulfenylation and O-deallylation could be significantly improved. A comparison of the reaction rates of O-deallylation and ester reduction demonstrated that O-deallylation was more sensitive to US irradiation. Finally, these products were evaluated for their antiproliferative activities, and most of them showed moderate to potent activities against three human cancer cell lines in vitro.

SUBMITTER: Wen Z

PROVIDER: S-EPMC4820744 | biostudies-literature | 2016 Apr

REPOSITORIES: biostudies-literature

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Ultrasound-promoted two-step synthesis of 3-arylselenylindoles and 3-arylthioindoles as novel combretastatin A-4 analogues.

Wen Zhiyong Z Li Xiaona X Zuo Daiying D Lang Binyue B Wu Yang Y Jiang Mingyang M Ma Huizhuo H Bao Kai K Wu Yingliang Y Zhang Weige W

Scientific reports 20160405

A series of 3-(3'-hydroxy-4'-methoxyphenyl)selenyl-5,6,7-trimethoxy-1H-indoles and 3-(3'-hydroxy-4'-methoxyphenyl)thio-5,6,7-trimethoxy-1H-indoles were obtained as a new class of combretastatin A-4 (CA-4) analogues via a convenient ultrasound (US)-assisted two-step process involving 3-selenenylation/sulfenylation followed by O-deallylation. With the assistance of US irradiation, both the reaction rates and yields of selenenylation, sulfenylation and O-deallylation could be significantly improved ...[more]

PMID: 27045272

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