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

doi:10.1002/slct.201803816

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

Houston Methodist

Research output: Contribution to journal › Article › peer-review

19 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 language	English (US)
Pages (from-to)	2281-2287
Number of pages	7
Journal	ChemistrySelect
Volume	4
Issue number	8
DOIs	https://doi.org/10.1002/slct.201803816
State	Published - Feb 28 2019

Keywords

Antibacterial activity
C−H activation
Metal free
Quinones
Thiomethylation

ASJC Scopus subject areas

General Chemistry

Divisions

Infectious Disease

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10.1002/slct.201803816

Cite this

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title = "Metal-Free C-H Thiomethylation of Quinones Using Iodine and DMSO and Study of Antibacterial Activity",

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).",

keywords = "Antibacterial activity, C−H activation, Metal free, Quinones, Thiomethylation",

author = "Sakthidevi Rajasekar and Krishna, \{T. P.Adarsh\} and Nagendran Tharmalingam and Ilangovan Andivelu and Eleftherios Mylonakis",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/slct.201803816",

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AU - Rajasekar, Sakthidevi

AU - Krishna, T. P.Adarsh

AU - Tharmalingam, Nagendran

AU - Andivelu, Ilangovan

AU - Mylonakis, Eleftherios

PY - 2019/2/28

Y1 - 2019/2/28

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AB - 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).

KW - Antibacterial activity

KW - C−H activation

KW - Metal free

KW - Quinones

KW - Thiomethylation

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

Abstract

Keywords

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