Highly Diastereoselective Route to α-Glucosidase Inhibitors, Neosalacinol and Neoponkoranol

Genzoh Tanabe; Youya Matsuda; Misato Oka; Yousuke Kunikata; Nozomi Tsutsui; Weija Xie; Gorre Balakishan; Mumen F A Amer; Shinsuke Marumoto; Osamu Muraoka

doi:10.1021/acs.joc.5b02894

Highly Diastereoselective Route to α-Glucosidase Inhibitors, Neosalacinol and Neoponkoranol

J Org Chem. 2016 Apr 15;81(8):3407-15. doi: 10.1021/acs.joc.5b02894. Epub 2016 Apr 7.

Authors

Genzoh Tanabe, Youya Matsuda, Misato Oka, Yousuke Kunikata, Nozomi Tsutsui, Weija Xie¹, Gorre Balakishan², Mumen F A Amer³, Shinsuke Marumoto, Osamu Muraoka

Affiliations

¹ State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, P. R. China.
² Department of Organic Chemistry, Telangana University , Nizamabad 503322, Telangana State, India.
³ Faculty of Pharmacy, Applied Science Private University , Al Arab St 21, Amman 11931, Jordan.

PMID: 27015084
DOI: 10.1021/acs.joc.5b02894

Abstract

A facile and highly diastereoselective route to potent natural α-glucosidase inhibitors, i.e., neosalacinol (4) and neoponkoranol (6), isolated from the traditional Ayurvedic medicine "Salacia" was developed by intramolecular cyclization of appropriately substituted sulfides (9 and 12).

Publication types

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

MeSH terms

Cyclization
Glycoside Hydrolase Inhibitors / chemistry*
Glycoside Hydrolase Inhibitors / pharmacology*
Plant Extracts / chemistry*
Plant Extracts / isolation & purification
Salacia / chemistry*
Stereoisomerism
Structure-Activity Relationship
Sugar Alcohols / chemistry*
Sugar Alcohols / pharmacology*
Sulfates / chemistry*
Sulfates / pharmacology*
Sulfides / chemistry*
Thiophenes / chemistry*
Thiophenes / pharmacology*

Substances

1,4-dideoxy-1,4-((2,3,4,5,6-pentahydroxyhexyl)episulfoniumylidene)arabinitol
Glycoside Hydrolase Inhibitors
Plant Extracts
Sugar Alcohols
Sulfates
Sulfides
Thiophenes
salacinol