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Metal‐Free C‐H Thiomethylation of Quinones Using Iodine and DMSO and Study of Antibacterial Activity
Author(s) -
Rajasekar Sakthidevi,
Krishna T. P. Adarsh,
Tharmalingam Nagendran,
Andivelu Ilangovan,
Mylonakis Eleftherios
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201803816
Subject(s) - staphylococcus aureus , antibacterial activity , chemistry , substituent , antimicrobial , iodine , dimethyl sulfoxide , yield (engineering) , biphenyl , combinatorial chemistry , medicinal chemistry , organic chemistry , bacteria , biology , materials science , genetics , metallurgy
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).