Document Report Card

ID: ALA1137581

Journal: J Med Chem

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

Authors: Vyavahare VP, Chakraborty C, Maity B, Chattopadhyay S, Puranik VG, Dhavale DD.

Abstract: Two new C-1 epimeric hydroxymethyl castanospermine congeners 2a and 2b, synthesized by stereocontrolled 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.

CiteXplore: 17918922

DOI: 10.1021/jm070660f