DDQ mediated stereoselective intermolecular benzylic CN bond formation: Synthesis of (−)-cytoxazone, (−)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity

A short and efficient strategy for the synthesis of (−)-cytoxazone, (−)-4-epi-cyoxazone and their analogues by using DDQ mediated diastereoselective intermolecular benzylic amination has been described. Immunological evaluation of their cytokine modulating activity revealed that the change of hydrox...

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Bibliographic Details
Published in:Tetrahedron 2017-03, Vol.73 (11), p.1473-1481
Main Authors: Lingamurthy, Macha, Nalliboina, Gopalal Rao, Rao, Maddimsetti Venkateswara, Rao, Batchu Venkateswara, Reddy, Bonam Srinivasa, Sampath Kumar, Halmuthur Mahabalarao
Format: Article
Language:English
Subjects:
Benzylic amination
Cellular immunity
Cytoxazone
Oxazolidine
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Summary:A short and efficient strategy for the synthesis of (−)-cytoxazone, (−)-4-epi-cyoxazone and their analogues by using DDQ mediated diastereoselective intermolecular benzylic amination has been described. Immunological evaluation of their cytokine modulating activity revealed that the change of hydroxy methyl to methyl group increased the cellular immunity in in-vitro cultures. Changes in the stereochemistry of oxazolidine haven't influenced the biological activity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.01.059