Metal-Free C-H Thiomethylation of Quinones Using Iodine and DMSO and Study of Antibacterial Activity

Sakthidevi Rajasekar, T. P.Adarsh Krishna, Nagendran Tharmalingam, Ilangovan Andivelu, Eleftherios Mylonakis

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

A novel, transition metal-free, molecular iodine mediated method for thiomethylation of quinones, using dimethyl sulfoxide (DMSO) as a benign thiomethylating agent is described. This greener reaction protocol leads to selective mono thiomethylation in low to high yield and tolerates a range of substituent groups. Preliminary antibacterial evaluation of thiomethylated quinones, carried out against methicillin resistant Staphylococcus aureus shows promising results. One of the compound 3′-methyl-6-(methylthio)-[1,1′-biphenyl]-2,5-dione exhibited antimicrobial activity even against clinical isolates of S. aureus and vancomycin-intermediate Staphylococcus aureus (VISA).

Original languageEnglish (US)
Pages (from-to)2281-2287
Number of pages7
JournalChemistrySelect
Volume4
Issue number8
DOIs
StatePublished - Feb 28 2019

Keywords

  • Antibacterial activity
  • C−H activation
  • Metal free
  • Quinones
  • Thiomethylation

ASJC Scopus subject areas

  • Chemistry(all)

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