Synthesis of novel D-ring fused 7鈥?aryl-androstano[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines

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• 作者：Li-Hua Huang^a ; ^b ; Yong-Fei Zheng^a ; Chuan-Jun Song^b ; Yan-Guang Wang^a ; Zhi-Yu Xie^a ; Yao-Wen Lai^a ; Yong-Zheng Lu^b ; Hong-Min Liu^a ; ^b ; ^c ; ^{liuhm@zzu.edu.cn} ; ^{liuhm@public2.zz.ha.cn}
• 关键词：Heterosteroids ; Steroidal[17 ; 16-d]triazolopyrimidines ; 3-Amino-1 ; 2 ; 4-triazole ; 16-Arylidene-17-ketosteroids ; 1 ; 2 ; 4-Triazolo[1 ; 5-a]pyrimidine
• 刊名：Steroids
• 出版年：2012
• 期刊代码：142_0039128x
• 类别：bio
• 出版时间：April, 2012
• 卷：77
• 期：5
• 页码：367-374
• 文件大小：890 K

摘要

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 (lass="boldFont">1a) and dehydroepiandrosterone (DHEA, lass="boldFont">1b) with aromatic aldehydes was catalyzed by KF/Al₂O₃ to give the corresponding 3-oxo-4-aza-5伪- and 3尾-hydroxy-5-en-16-arylidene-17-ketosteroids (lass="boldFont">2a-lass="boldFont">r). Subsequently, the intermediates lass="boldFont">2a-lass="boldFont">r reacted with dinucleophilic 3-amino-1,2,4-triazole in presence of t-BuOK to afford the title compounds (lass="boldFont">3a-lass="boldFont">r). All the synthesized heterosteroids are new and are currently being evaluated for their biological activities.