Synthesis of D-ring-substituted (5鈥?span style='font-style: italic'>R)- and (5鈥?span style='font-style: italic'>S)-17尾-pyrazolinylandrostene epimers and comparison of their potential anticancer activities

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• 作者：Zoltá ; n Ivá ; nyi^a ; Nikoletta Szabó ; ^a ; ^b ; Judit Huber^a ; Já ; nos Wö ; lfling^a ; Istvá ; n Zupkó ; ^c ; Mihá ; ly Szé ; csi^b ; Tibor Wittmann^b ; Gyula Schneider^a ; ^{schneider@chem.u-szeged.hu}
• 关键词：Aldol condensation ; Pregnenolone ; Hydrazine ; Pyrazoline ; Epimers ; Anticancer activities
• 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：566-574
• 文件大小：313 K

摘要

Various steroidal benzylidenes were synthetized from pregnenolone with benzaldehyde and p-substituted benzaldehydes. The resulting 17尾-chalconyl derivatives of pregnenolone were reacted with hydrazine hydrate in acetic acid solution. Regardless of the starting material, the ring-closure reaction afforded (in contrast with the literature data) a mixture of two steroidal pyrazoline epimers. The epimers were critical isomer pairs, which could be separated only in their acetylated form; their structures were investigated by NMR techniques. The in vitro inhibition of rat testicular C_17,20-lyase activity and the antiproliferative effects on four human cancer cell lines were measured, and the results obtained from the two epimer series were compared.