Bioorganic and Medicinal Chemistry p. 921 - 939 (1997)
Update date:2022-08-05
Topics: Synthesis Biological Evaluation
Uchida, Chikara
Kimura, Hiroshi
Ogawa, Seiichiro
Twenty-four stereoisomers of 5-amino- and 5-amino-C-(hydroxymethyl)-1,2,3,4-cyclopentanetetraols and twenty-six of the corresponding N-phenyl cyclic isourea derivatives were assayed for inhibitory activity against six glycosidases. Among them, as has been expected for structure mimics of putative transition state glucopyranosyl cation for glycoside hydrolysis, 1L-(1,2,4,5/3)-5-amino-1-C-(hydroxymethyl)-1,2,3,4-cyclopentanetetraol L-4 and its N-phenyl cyclic isourea derivative S-19 were shown to have strong inhibitory activity, IC50 4 x 10-7 and 7.6 x 10-9 M, respectively, against baker's yeast a-glucosidase. It has been analogously explained that compounds R,S-22 and R,S-26 possessed high inhibitory potency against Escherichia coli and bovine liver β-galactosidases, respectively.
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Doi:10.3390/molecules25173993
(2020)Doi:10.1016/S0040-4039(97)01156-8
(1997)Doi:10.1016/0960-894X(95)00563-9
(1996)Doi:10.1021/jo9707085
(1997)Doi:10.1039/a700987i
(1997)Doi:10.1016/S0022-2860(97)00084-7
(1997)