Novel 4-azasteroidal N-glycoside analogues bearing sugar-like D ring: synthesis and anticancer activities.

Abstract

A series of novel N-glycoside analogues with 4-azasteroid moiety bearing sugar-like D ring were conveniently synthesized by constructing the core dihydropyran ring embedded in 4-azasteroidal skeleton which was prepared from 4-aza-5α-androst-3,17-dione 1 in four steps. The structure of 6b were unambiguously proved by the appropriate X-ray structural analysis. Anticancer activity was found for all of the analogues with purinyl moiety against breast cancer (MCF-7), human neuroblastoma (SK-N-SH), cervical cancer cell (HeLa) and prostatic cancer (PC-3), while the analogue 7 containing 1,2,4-triazole heterocycle as the nucleobase was inactive against all of the tested cancer cell lines. The biology results showed the purinyl moiety attached to the pyran ring of 6a-d, substituent at 6'-position of purine base and introduction of a halogen atom at 2'-position of 6'-chloropurine had obviously effect on the evaluated anticancer activity.

• Authors: Li-Hua Huang, Yan-Guang Wang, Gong Xu, Xiang-Hua Zhang, Yong-Fei Zheng, Hui-Li He, Wen-Zheng Fu, Hong-Min Liu
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 21 Issue 20 Pg. 6203-5 (Oct 15 2011) ISSN: 1464-3405 [Electronic] England
• PMID: 21889341 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2011 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents
• Azasteroids
• Glycosides

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Azasteroids (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Cell Survival (drug effects)
• Female
• Glycosides (chemical synthesis, chemistry, pharmacology)
• Humans
• Male
• Neoplasms (drug therapy)