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

Chang-Ching Lin; Yi-Shin Pan; Laxmikant N Patkar; Hsiu-Mei Lin; Der-Lii M Tzou; Thangaiah Subramanian; Chun-Cheng Lin

doi:10.1016/j.bmc.2004.03.064

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

Bioorg Med Chem. 2004 Jun 15;12(12):3259-67. doi: 10.1016/j.bmc.2004.03.064.

Authors

Chang-Ching Lin¹, Yi-Shin Pan, Laxmikant N Patkar, Hsiu-Mei Lin, Der-Lii M Tzou, Thangaiah Subramanian, Chun-Cheng Lin

Affiliation

¹ Department of Chemistry, Tsing Hua University, Hsinchu 300, Taiwan. cclin@chem.sinica.edu.tw

PMID: 15158794
DOI: 10.1016/j.bmc.2004.03.064

Abstract

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 beta-glucosidase with Ki 26.3 microM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Cyclization
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology*
Glycoside Hydrolases / antagonists & inhibitors
Glycoside Hydrolases / metabolism
Hydroxylation
Imines / chemical synthesis
Imines / chemistry*
Imines / pharmacology*
Molecular Conformation
Molecular Structure
Stereoisomerism

Substances

Enzyme Inhibitors
Imines
Glycoside Hydrolases