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

Macha Lingamurthy, Gopalal Rao Nalliboina, Maddimsetti Venkateswara Rao, Batchu Venkateswara Rao, Bonam Srinivasa Reddy, Halmuthur Mahabalarao Sampath Kumar

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1473-1481
Number of pages9
JournalTetrahedron
Volume73
Issue number11
DOIs
StatePublished - 2017
Externally publishedYes

Keywords

  • Benzylic amination
  • Cellular immunity
  • Cytoxazone
  • Oxazolidine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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