Indole Grignard reaction. III. Synthesis, crystal structure, and analgesic activity of (R)- and (S)-3-amino-2,3,4,9-tetrahydrothiopyrano[2,3-b]indoles.
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-2,3,4,9-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.
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan.
N
N
Ishizuka
T
T
Sato
Y
Y
Makisumi
D000700:Analgesics / Q000138:chemical synthesis*; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003460:Crystallization; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D014961:X-Ray Diffraction
D000700:Analgesics; D007202:Indicators and Reagents; D007211:Indoles; D011714:Pyrans