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

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

Journal of medicinal chemistry (2007-10-09)
Vinod P Vyavahare, Chaitali Chakraborty, Biswanath Maity, Subrata Chattopadhyay, Vedavati G Puranik, Dilip D Dhavale
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.

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Sigma-Aldrich
(1S,6S,7R,8R,8aR)-1,6,7,8-Tetrahydroxyindolizidine, 98%