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

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Both enantiomers of the title compounds were synthesized and the crystal structure of one 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, 3, 4, 9-tetrahydrothiopyrano[2, 3-b]indole (1), Isoxal^[○!R]. and Tiavamide^[○!R]. The (R)-isomers were more potent than the corresponding (S)-isomers, and were more potent than Isoxal and Tiaramide, but less potent than 1.