Versatile approach for the synthesis of novel seven-membered iminocyclitols via ring-closing metathesis dihydroxylation reaction

Graphic Seven-membered iminocyclitols with diverse diastereomers were prepared starting with d- and l-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive i...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 2004-06, Vol.12 (12), p.3259-3267
Hauptverfasser:	Lin, Chang-Ching, Pan, Yi-shin, Patkar, Laxmikant N, Lin, Hsiu-Mei, Tzou, Der-Lii M, Subramanian, Thangaiah, Lin, Chun-Cheng
Format:	Artikel
Sprache:	eng
Schlagworte:	Analytical, structural and metabolic biochemistry Biological and medical sciences Crystallography, X-Ray Cyclization Dihydroxylation Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzymes and enzyme inhibitors Fundamental and applied biological sciences. Psychology Glycosidase inhibitor Glycoside Hydrolases - antagonists & inhibitors Glycoside Hydrolases - metabolism Hydrolases Hydroxylation Imines - chemical synthesis Imines - chemistry Imines - pharmacology Iminocyclitols Medical sciences Miscellaneous Molecular Conformation Molecular Structure Pharmacology. Drug treatments Ring-closing metathesis Stereoisomerism
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Zusammenfassung:	Graphic Seven-membered iminocyclitols with diverse diastereomers were prepared starting with d- and l-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive inhibitor for β-glucosidase with K i 26.3 μM.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2004.03.064