Structure-activity relationships among analogues of pemedolac, cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole-1-acetic acid, a potent analgesic agent

The syntheses of analogues of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano(3,4-b)indo le-1-acetic acid), a potent analgesic, are described. They were tested for analgesic and antiinflammatory effects in vivo and for inhibition of prostaglandin production in vitro. Analysis of st...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1988-11, Vol.31 (11), p.2211-2217
Main Authors: Mobilio, Dominick, Humber, Leslie G, Katz, Alan H, Demerson, Christopher A, Hughes, Philip, Brigance, Robert, Conway, Kimberly, Shah, Uresh, Williams, Gail
Format: Article
Language:English
Subjects:
Biological and medical sciences
Bones, joints and connective tissue. Antiinflammatory agents
Medical sciences
Pharmacology. Drug treatments
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Summary:The syntheses of analogues of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano(3,4-b)indo le-1-acetic acid), a potent analgesic, are described. They were tested for analgesic and antiinflammatory effects in vivo and for inhibition of prostaglandin production in vitro. Analysis of structure-activity relationships shows that analgesic activity in this series is associated with 1S-cis stereochemistry, the presence of a pi -system (allyl or benzyl) at position 4, and a log P value greater than 4.0.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00119a024