Acylhydrazones of 20-Keto Steroids and Their Transformations: I. Synthesis and Properties of 1′-Acyl-Substituted 3′-Methylandrosteno[16,17-d]Pyrazolines
A. V. Kamernitsky1 #, 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: email@example.com
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