Amidine, amidrazone, and amidoxime derivatives of monosaccharide aldonolactams: synthesis and evaluation as glycosidase inhibitors

G Papandreou, MK Tong, B Ganem

Index: Papandreou; Tong; Ganem Journal of the American Chemical Society, 1993 , vol. 115, # 25 p. 11682 - 11690

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Citation Number: 111

Abstract

Abstract: The synthesis of amidine, amidrazone, and amidoxime derivatives of D-glucono, D- mannono, and D-galactonolactams, which are potent glycosidase inhibitors, is described. With their sugar-like structures and resonancestabilized, partially positively charged anomeric carbons, these monosaccharide analogs mimic key conformational and electrostatic features of the corresponding glycopyranosyl cations. In the D-glUC0 series, ...