Synthesis and antifertility activity of zoapatanol analogs

The synthesis of and guinea pig contragestational screening data for several oxepane and 3,8-dioxabicyclo[3.2.1]octane analogues of zoapatanol (1) are described and their structure-activity relationships discussed. Conversion of the 5-keto group on the nonenyl side chain of 1 into a hydroxyl functio...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1985-06, Vol.28 (6), p.796-803
Main Authors: Kanojia, Ramesh M, Chin, Eva, Smith, Carol, Chen, Robert, Rowand, Deborah, Levine, Seymour D, Wachter, Michael P, Adams, Richard E, Hahn, DoWon
Format: Article
Language:English
Subjects:
Abortifacient Agents - chemical synthesis
Abortifacient Agents, Nonsteroidal - chemical synthesis
Abortifacient Agents, Nonsteroidal - pharmacology
Alicyclic compounds, terpenoids, prostaglandins, steroids
Animals
Chemistry
Exact sciences and technology
Female
Guinea Pigs
Montanoa
Organic chemistry
Oxepins - pharmacology
Pregnancy
Preparations and properties
Structure-Activity Relationship
Terpenoids
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Summary:The synthesis of and guinea pig contragestational screening data for several oxepane and 3,8-dioxabicyclo[3.2.1]octane analogues of zoapatanol (1) are described and their structure-activity relationships discussed. Conversion of the 5-keto group on the nonenyl side chain of 1 into a hydroxyl function enhanced the potency. Further significant enhancement in the potency was realized with the transformation of several oxepanes into the 3,8-dioxabicyclo-[3.2.1]octane-1-acetic acid derivatives. Detailed, comparative contragestational evaluation of the three most potent compounds 9, 33, and 37 is presented, which led to the selection of 33 (ORF 13811) for further biological evaluation.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00383a018