Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents

TitleSynthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents
Publication TypeJournal Article
Year of Publication2007
AuthorsVyavahare, VP, Chakraborty, C, Maity, B, Chattopadhyay, S, Puranik, VG, Dhavale, DD
JournalJournal of Medicinal Chemsitry
Volume50
Issue22
Pagination5519-5523
Date PublishedNOV
Type of ArticleArticle
ISSN0022-2623
Abstract

Two new C-1 epimeric hydroxymethyl castanospermine congeners 2a and 2b, synthesized by stereocon trolled intramolecular double reductive amination Of D-glucose derived beta-keto ester as a key step, showed impressive immuno-potentiating property. The bioactivity was mediated through up-regulation of T-H1/T-H2 cytokine ratio. The finding suggested that immunmodulatory activity of polyhydroxylated indolizidine alkaloids can be tuned by minor structural/stereochemical alterations.

DOI10.1021/jm070660f
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

5.589

Divison category: 
Center for Material Characterization (CMC)
Physical and Materials Chemistry