Cu-mediated N-arylation of 1,2,3-triazin-4-ones: Synthesis of fused triazinone derivatives as potential inhibitors of chorismate mutase

K. Shiva Kumar, Raju Adepu, Sandhya Sandra, D. Rambabu, G. Rama Krishna, C. Malla Reddy, Parimal Misra, Manojit Pal

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

A rapid and direct access to N-aryl substituted fused triazinone derivatives has been accomplished via N-arylation of 1,2,3-triazin-4-one ring involving a Cu-mediated coupling between triazinone derivatives and aryl boronic acids. A combination of Cu(OAc) 2-Et 3N in 1,2-dichloroethane was found to be effective and various fused triazinone derivatives have been prepared by using this methodology. Molecular structure of a representative compound was confirmed by single crystal X-ray diffraction study. The scope and limitations of this reaction is discussed. Some of the compounds synthesized were tested for chorismate mutase inhibitory properties in vitro. The in vitro dose response study of an active compound is presented.

Original languageEnglish
Pages (from-to)1146-1150
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number2
DOIs
StatePublished - 15 Jan 2012
Externally publishedYes

Keywords

  • 1,2,3-Triazin-4-one
  • Chorismate mutase
  • Copper
  • Coupling

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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