Potential Antifertility Agents. 4. Biological Properties of Diastereoisomeric 4-Aryl-2-methylcyclohexanecarboxylic Acids and Related Compounds | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

8703568

Reference Type

Journal Article

Title

Potential Antifertility Agents. 4. Biological Properties of Diastereoisomeric 4-Aryl-2-methylcyclohexanecarboxylic Acids and Related Compounds

Author(s)

Crenshaw, RR; Luke, GM; Jenks, TA; Partyka, RA; Bialy, G; Bierwagen, ME

Year

1973

Is Peer Reviewed?

Yes

Journal

Journal of Medicinal Chemistry
ISSN: 0022-2623
EISSN: 1520-4804

Volume

Issue

Page Numbers

813-823

Language

English

DOI

10.1021/jm00265a015

Abstract

Syntheses and biological activities are reported for the four (±) diastereoisomers of 4-(p-methoxyphenyl)-2-methylcyclohexanecarboxylic acid and for 75 related compounds. Antifertility, estrogenic, hypochol-esterolemic, and gonadotropin inhibitory activities are discussed. Biological activity resided in the (±)-1α,2β,4β and (±)-1β,2β,4α isomers. Evidence is presented that the activity in these isomers is owing to their stereochemical relationship with steroidal estrogens. One of the compounds (5b) which showed an unexpectedly large separation between uterotropic and gonadotropin inhibitory activities is discussed more extensively and is suggested for possible utility in the treatment of prostatic cancrr and benign prostatic hypertrophy. 1973, American Chemical Society. All rights reserved.