Indole Grignard Reaction: III: Synthesis, Crystal Structure, and Analgesic Activity of (R)- and (A)-3-Amino-2,3,4,9-tetrahydrothiopyrano[2,3-b]indoles

Abstract

Both enantiomers of the title compounds were synthesized and the crystal structure of one of them was determined by X-ray crystallography. The indole Grignard reaction was effective for synthesizing the key intermediate of the (R)-isomers. The analgesic activities of the products were compared with those of 4-methylaminomethyl-2,394,9-tetrahydrothiopyrano[2,3-b]indole (1), Isoxal®, and Tiaramide®. The (R)-isomers were more potent than the corresponding (S)-isomers, and were more potent than Isoxal and Tiaramide, but less potent than 1. © 1990, The Pharmaceutical Society of Japan. All rights reserved.