title: Synthesis of novel D-ring fused 7'-aryl-androstano[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines.
abstract: The preparation of novel steroidal heterocycles containing the 7-aryl-substituted 1,2,4-triazolo[1,5-a]pyrimidine moiety fused to the 16,17-positions of the steroid nucleus is described. The Aldol reaction of 4-aza-androst-3,17-dione (1a) and dehydroepiandrosterone (DHEA, 1b) with aromatic aldehydes was catalyzed by KF/Al(2)O(3) to give the corresponding 3-oxo-4-aza-5α- and 3β-hydroxy-5-en-16-arylidene-17-ketosteroids (2a-r). Subsequently, the intermediates 2a-r reacted with dinucleophilic 3-amino-1,2,4-triazole in presence of t-BuOK to afford the title compounds (3a-r). All the synthesized heterosteroids are new and are currently being evaluated for their biological activities.
authors.affiliation: School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, China.
authors.forename: Li-Hua
authors.initials: LH
authors.lastname: Huang
authors.forename: Yong-Fei
authors.initials: YF
authors.lastname: Zheng
authors.forename: Chuan-Jun
authors.initials: CJ
authors.lastname: Song
authors.forename: Yan-Guang
authors.initials: YG
authors.lastname: Wang
authors.forename: Zhi-Yu
authors.initials: ZY
authors.lastname: Xie
authors.forename: Yao-Wen
authors.initials: YW
authors.lastname: Lai
authors.forename: Yong-Zheng
authors.initials: YZ
authors.lastname: Lu
authors.forename: Hong-Min
authors.initials: HM
authors.lastname: Liu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000732:Androstanols / Q000737:chemistry; D003687:Dehydroepiandrosterone / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D011743:Pyrimidines / Q000737:chemistry*; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000732:Androstanols; D006571:Heterocyclic Compounds; D011743:Pyrimidines; D013256:Steroids; D014230:Triazoles; C000658:androstan-3-ol; D003687:Dehydroepiandrosterone; C030986:pyrimidine