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Synthesis and analgesic activity of pemedolac [cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole-1-acetic acid]

1988; American Chemical Society; Volume: 31; Issue: 6 Linguagem: Inglês

10.1021/jm00401a029

1520-4804

Alan H. Katz, Christopher A. Demerson, C. C. Shaw, A. A. ASSELIN, Leslie G. Humber, Kimberly M. Conway, Gregory Gavin, Charles J. Guinosso, Norman P. Jensen,

Chemical synthesis and alkaloids

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.