Abstract
Various steroidal benzylidenes were synthetized from pregnenolone with benzaldehyde and p-substituted benzaldehydes. The resulting 17β-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.
Copyright © 2012 Elsevier Inc. All rights reserved.
Publication types
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Comparative Study
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetic Acid / chemistry
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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Cell Survival / drug effects
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HeLa Cells
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Humans
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Hydrazines / chemistry
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Isomerism
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Male
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Models, Chemical*
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Molecular Structure
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Pyrazoles / chemical synthesis*
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Pyrazoles / chemistry
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Pyrazoles / pharmacology
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Rats
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Rats, Wistar
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Steroid 17-alpha-Hydroxylase / antagonists & inhibitors
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Steroid 17-alpha-Hydroxylase / metabolism
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Steroids / chemical synthesis*
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Steroids / chemistry
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Steroids / pharmacology
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Testis / enzymology
Substances
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Antineoplastic Agents
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Hydrazines
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Pyrazoles
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Steroids
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hydrazine
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Steroid 17-alpha-Hydroxylase
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Acetic Acid