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

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 unambi...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2011-10, Vol.21 (20), p.6203-6205
Main Authors: Huang, Li-Hua, Wang, Yan-Guang, Xu, Gong, Zhang, Xiang-Hua, Zheng, Yong-Fei, He, Hui-Li, Fu, Wen-Zheng, Liu, Hong-Min
Format: Article
Language:English
Subjects:
4-Azasteroidal N-glycoside analogues
Anticancer activities
anticarcinogenic activity
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Azasteroids - chemical synthesis
Azasteroids - chemistry
Azasteroids - pharmacology
Biological and medical sciences
breast neoplasms
Cell Line, Tumor
Cell Survival - drug effects
Diol
Female
General aspects
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosides - pharmacology
Humans
Male
Medical sciences
Neoplasms - drug therapy
Pharmacology. Drug treatments
prostatic neoplasms
Selective oxidation
Sugar-like D ring
Synthesis
uterine cervical neoplasms
X-radiation
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Summary: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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2011.07.049