Synthesis and analgesic activity of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]ind ole-1- acetic acid).
The synthesis of cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole -1-acetic acid, pemedolac (USAN), is described. This compound has been found to be a potent analgesic agent in primary screening. Pemedolac has been resolved and the active (+)-enantiomer assigned a 1S,4R absolute configuration on the basis of a crystallographic analysis of its (S)-(-)-borneol ester.
Katz
A H
AH
Ayerst Laboratories Research, Inc., Princeton, New Jersey 08543-8000.
Demerson
C A
CA
Shaw
C C
CC
Asselin
A A
AA
Humber
L G
LG
Conway
K M
KM
Gavin
G
G
Guinosso
C
C
Jensen
N P
NP
Mobilio
D
D
D000085:Acetates / Q000138:chemical synthesis* / Q000494:pharmacology; D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000494:pharmacology; D007210:Indoleacetic Acids; D008297:Male; D051379:Mice; D008968:Molecular Conformation; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D000085:Acetates; D000700:Analgesics; D000893:Anti-Inflammatory Agents; D007210:Indoleacetic Acids; C056040:pemedolac