Literature DB >> 17918922

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

Vinod P Vyavahare1, 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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Year:  2007        PMID: 17918922     DOI: 10.1021/jm070660f

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  2 in total

1.  Synthesis of C-Pseudonucleosides Bearing Thiazolidin-4-one as a Novel Potential Immunostimulating Agent.

Authors:  Hua Chen; Qingmei Yin; Chunxiao Li; Enkai Wang; Fang Gao; Xiaobo Zhang; Zhi Yin; Sinan Wei; Xiaoliu Li; Ming Meng; Pingzhu Zhang; Na Li; Jinchao Zhang
Journal:  ACS Med Chem Lett       Date:  2011-09-07       Impact factor: 4.345

2.  Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones.

Authors:  Marco Bonanni; Marco Marradi; Francesca Cardona; Stefano Cicchi; Andrea Goti
Journal:  Beilstein J Org Chem       Date:  2007-12-12       Impact factor: 2.883

  2 in total

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