title: Structure-activity relationships among analogues of pemedolac, cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indo le-1-a cetic acid, a potent analgesic agent.
abstract: The syntheses of analogues of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indol e-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.
authors.affiliation: Ayerst Laboratories Research Inc., Princeton, New Jersey 08543-8000.
authors.forename: D
authors.initials: D
authors.lastname: Mobilio
authors.forename: L G
authors.initials: LG
authors.lastname: Humber
authors.forename: A H
authors.initials: AH
authors.lastname: Katz
authors.forename: C A
authors.initials: CA
authors.lastname: Demerson
authors.forename: P
authors.initials: P
authors.lastname: Hughes
authors.forename: R
authors.initials: R
authors.lastname: Brigance
authors.forename: K
authors.initials: K
authors.lastname: Conway
authors.forename: U
authors.initials: U
authors.lastname: Shah
authors.forename: G
authors.initials: G
authors.lastname: Williams
authors.forename: F
authors.initials: F
authors.lastname: Labbadia
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology; D004487:Edema / Q000517:prevention & control; D066298:In Vitro Techniques; D007210:Indoleacetic Acids / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D011453:Prostaglandins / Q000096:biosynthesis; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D007210:Indoleacetic Acids; D011453:Prostaglandins; C056040:pemedolac