Synthesis and Biological Activity of Some 17a-Substituted Homolactones of Androst-5-ene Derivatives

Autor:	Evgenija A. Djurendić, Dora Molnar-Gabor, Dušan Lazar, Srdjan Z. Stojanović, Katarina M. Penov Gaši, Marija N. Sakač, R. Kovacevic, János Csanádi
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Potassium hydroxide Structure analysis Biological activity General Chemistry General Medicine Medicinal chemistry chemistry.chemical_compound Enzyme chemistry Organic chemistry X ray analysis Ethylene glycol Ene reaction
Zdroj:	ChemInform. 37
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200612192
Popis:	Some new 17a-homolactones were prepared from 3β-hydroxy-16-(hydroxyimino)androst-5-en-17-one (1) as a starting compound, which was transformed first to the corresponding 17α-phenyl and 17α-benzyl derivatives 2 and 3. The structure of compound 3 was confirmed by X-ray structure analysis. Beckmann fragmentation of compounds 2 and 3 yielded 16,17-seco-cyano ketones 4-7, whose reduction with NaBH4 gave 16,17-seco-cyano alcohols 8-11, whereby the structure of compound 7 was established by X-ray structural analysis. Compounds 8-11 served as the starting compounds for obtaining lactones 12 and 13 in a reaction with potassium hydroxide in ethylene glycol. One-pot procedures were also developed for preparing 17a-homolactones 12, 13 and 16 from the hydroxyimino alcohols 2, 3 and 14. Compounds 12 and 13 showed an inhibitory activity against the enzyme aromatase (63 and 59%, respectively).
Databáze:	OpenAIRE
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