Acylhydrazones of 20-Keto Steroids and Their Transformations: I. Synthesis and Properties of 1′-Acyl-Substituted 3′-Methylandrosteno[16,17-d]Pyrazolines

A. V. Kamernitsky^1 #, E. I. Chernoburova¹, V. V. Chertkova¹, I. V. Zavarzin¹, V. N. Yarovenko¹ and M. M. Krayushkin¹

^#Phone: (495) 137-73-31; fax: (495) 135-53-28; e-mail: kamer@ioc.ac.ru

¹Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

Received: August  28,  2006; in final form: October  3,  2006

Abstract.  Acetates of 3β-hydroxy-3′-methyl-1′(N)-acylandrost-5-eno[16,17-d]pyrazolines bearing monothiooxamide acyl groups were synthesized during the study of approaches to the synthesis of 3′-methylandrosteno[16,17-d]azoles, promising biologically active analogues of 20-keto pregnenanes, and their properties were investigated. The cyclization of Δ¹⁶-20-thiooxamidohydrazones to the corresponding heterocycles was shown to proceed under rigorous conditions and to depend partially on the nature of the oxamide grouping.

Key words: cyclization, heterocyclic steroids, 3β-hydroxy-3′-methyl-1′(N)-acylandrost-5-eno[16,17-d]pyrazolines, 3β-hydroxy-3′-methylandrost-5-eno[16,17-d]pyrazole, Δ¹⁶-20-thiooxamidohydrazones

Russian Journal of Bioorganic Chemistry 2007, 33 (3): 315-319