Synthesis of 1-deoxy-1-hydroxymethyl- and 1-deoxy-1-epi-hydroxymethyl castanospermine as new potential immunomodulating agents |
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| Authors: | Vyavahare Vinod P Chakraborty Chaitali Maity Biswanath Chattopadhyay Subrata Puranik Vedavati G Dhavale Dilip D |
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| Institution: | Garware Research Centre, Department of Chemistry, University of Pune, Pune-411 007, India. |
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| 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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