Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (9): 1864-1869.DOI: 10.6023/cjoc201402032 Previous Articles     Next Articles


黎龙香a, 谢龙勇a, 王风君b, 何卫民a, 向建南a   

  1. a 湖南大学化学化工学院, 长沙 410082;
    b 中南大学湘雅医院耳鼻喉科, 长沙 410082
  • 收稿日期:2014-02-27 修回日期:2014-04-15 发布日期:2014-05-05
  • 通讯作者: 何卫民, 向建南
  • 基金资助:

    国家自然科学基金(Nos. 21302048, 21276068)、中国博士后科学基金(No. 2013M540625)、湖南省自然科学基金(No. 11JJ5008)资助项目.

Synthesis and Antitumor Activity of 17-(2',5'-Disubstituted-oxazolyl)-androsta-4,16-dien-3-one

Li Longxianga, Xie Longyonga, Wang Fengjunb, He Weimina, Xiang Jiannana   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b Department of Otolaryngology-Head and Neck Surgery Xiangya Hospital, Central South University, Changsha 410082
  • Received:2014-02-27 Revised:2014-04-15 Published:2014-05-05
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21302048, 21276068), the China Postdoctoral Science Foundation (No. 2013M540625) and the Natural Science Foundation of Hunnan Province (No. 11JJ5008).

A series of 17-(2',5'-disubstituted-oxazolyl)-androsta-4,16-dien-3-one derivatives 4a~4k were designed and synthesized via the gold-catalyzed steroidal alkyne oxidation from 4-androstene-3,17-dione 1. The structures of the targeted compounds were characterized by 1H NMR, 13C NMR, IR and HRMS. These synthesized compounds were screened for in vitro antitumor activity by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay against MCF-7 (human breast cancer cell line), A549 (human lung cancer cell line), Bel-7402 (human liver cancer cell line), Hela (human cervical cancer cell line) and PC-3M-1E8 (human prostate cancer cell line) using abiraterone as the positive control. The results revealed that most of compounds showed moderate to significant activity. In particular, compounds 4c, 4g, 4i and 4j exhibited similar antitumor activities compared with that of abiraterone, and all tested compounds displayed higher selectivity against MCF-7 cell line (IC50=3.0~25.5 μmol/L).

Key words: steroids, oxazole, gold-catalyzed, synthesis, antitumor activity