title: 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: School of Pharmaceutical Science, Zhengzhou Univercity, Ke Xue Da Dao 100, Zhengzhou 450001, PR China.
authors: Li-Hua
authors: LH
authors: Huang
authors: Yan-Guang
authors: YG
authors: Wang
authors: Gong
authors: G
authors: Xu
authors: Xiang-Hua
authors: XH
authors: Zhang
authors: Yong-Fei
authors: YF
authors: Zheng
authors: Hui-Li
authors: HL
authors: He
authors: Wen-Zheng
authors: WZ
authors: Fu
authors: Hong-Min
authors: HM
authors: Liu
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001378:Azasteroids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005260:Female; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D008297:Male; D009369:Neoplasms / Q000188:drug therapy
chemical_list: D000970:Antineoplastic Agents; D001378:Azasteroids; D006027:Glycosides