Rapid Microwave Assisted Synthesis and Antiproliferative Evaluation of Novel Steroidal Thiazole Derivatives

doi:10.1007/s40242-017-6372-y

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (2): 206-212.doi: 10.1007/s40242-017-6372-y

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Rapid Microwave Assisted Synthesis and Antiproliferative Evaluation of Novel Steroidal Thiazole Derivatives

HUANG Yanmin¹, ZHAO Dandan¹, LIU Chang¹, GAN Chunfang¹, ZHAN Junyan¹, LIN Qifu², SHI Haixin², CUI Jianguo^1,2

1. College of Chemistry and Material Science, Guangxi Teachers Education University, Nanning 530001, P. R. China;
2. Guangxi Colleges and University Key Laboratory of Beibu Gulf Oil and Natural Gas Resource Effective Utilization, Qizhou University, Qizhou 535011, P. R. China

Received:2016-09-05 Revised:2016-09-18 Online:2017-04-01 Published:2017-03-23
Contact: CUI Jianguo,E-mail:cuijg1954@126.com E-mail:cuijg1954@126.com
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21462009, 21562007) and the Foundation of Guangxi Colleges and University Key Laboratory of Beibu Gulf Oil and Natural Gas Resource Effective Utilization, China(No. 2016kLOG10).

Abstract

Abstract:

Three series of novel steroidal thiazole derivatives were synthesized by microwave assisted one-pot reaction from pregnenolone, testosterone and estrone, respectively. Their structures were characterized by IR, NMR and HRMS, and the antiproliferative activities of all the synthesized compounds against human cervical carcinoma (HeLa), human liver carcinoma(HepG2), human lung carcinoma(A549), nasopharyngeal carcinoma(CNE2) and normal kidney epithelial cells(HEK293T) were screened. Among the compounds, 1-estron-17'-ylidene-2-[4'-(p-bromophenyl)-2'-thiazol]hydrazone(12) displayed distinct antiproliferative activity against all the tested cancer cell lines and was almost inactive to normal kidney epithelial cells.

Key words: Microwave assisted synthesis, Pregnenolone, Testosterone, Estrone, Steroidal thiazole derivative

HUANG Yanmin, ZHAO Dandan, LIU Chang, GAN Chunfang, ZHAN Junyan, LIN Qifu, SHI Haixin, CUI Jianguo. Rapid Microwave Assisted Synthesis and Antiproliferative Evaluation of Novel Steroidal Thiazole Derivatives[J]. Chemical Research in Chinese Universities, 2017, 33(2): 206-212.

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Rapid Microwave Assisted Synthesis and Antiproliferative Evaluation of Novel Steroidal Thiazole Derivatives

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