The syntheses of 5-pyridyl-3(beta-D-galactopyranosyl)-1,3,4-oxadiazole-2-thiones 3a-3c and 5-pyridyl-2(beta-D-galactopyranosyl)-4-benzyl-1,2, 4-triazole-3-thiones 6a-6c are reported. The existence of N-galactosides--not S-galactosides--was proven by IR and 15N NMR spectroscopy. The structures of the final products and the intermediates were elucidated by IR, 1H, 13C and 15N NMR spectroscopy and mass spectrometry.
Abstract1,3-Bis(arylsulfonyl)-benzimidazolones 1a-d were synthesized by reacting benzimidazolones with arenesulfonyl chlorides in the presence of NaOH. Mono(arylsulfonyl)-benzimidazolone derivatives 5a-c were prepared from benzimidazolone by protecting one of the Natoms with a tert-butoxycarbonyl group followed by arylsulfonylation and deprotection in acidic medium. The antidiabetic activity of three compounds 1a, 1c and 5a has been determined.
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