Synthesis and biological evaluation of 4,6-diethyl-1,3,4,5-tetrahydropyrano[4,3-b]indole-4-acetic acid, an isomer of etodolac.
The synthesis of 4,6-diethyl-1,3,4,5-tetrahydropyrano[4,3-b]indole-4-acetic acid, an isomer of the antiinflammatory agent etodolac, is described. The compound was found to have an ED50 of 3 mg/kg po in the rat curative adjuvant arthritis assay, and an IC50 of 50 nM for inhibiting prostaglandin production in cultured chondrocytes.
Hughes
P
P
Wyeth-Ayerst Research, Princeton, New Jersey 08543-8000.
DeVirgilio
J
J
Humber
L G
LG
Chau
T
T
Weichman
B
B
Neuman
G
G
D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000627:therapeutic use; D001169:Arthritis, Experimental / Q000188:drug therapy / Q000378:metabolism; D002358:Cartilage, Articular / Q000187:drug effects / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D015232:Dinoprostone / Q000096:biosynthesis; D017308:Etodolac; D007210:Indoleacetic Acids / Q000138:chemical synthesis* / Q000627:therapeutic use*; D051381:Rats; D013329:Structure-Activity Relationship
D000894:Anti-Inflammatory Agents, Non-Steroidal; D007210:Indoleacetic Acids; C060961:4,6-diethyl-1,3,4,5-tetrahydropyrano(4,3-b)indole-4-acetic acid; D017308:Etodolac; D015232:Dinoprostone