Issue 23, 2023

Metal-free, tert-butyl nitrite promoted C(sp2)–S coupling reaction: the synthesis of aryl dithiocarbamates and analysis of antimicrobial activity by ‘in silico’ and ‘in vitro’ methods for drug modification

Abstract

An environmentally friendly, metal-free, and efficient C(sp2)–S coupling reaction protocol between aniline and low-cost tetraalkylthiuram disulfides was developed to synthesize aryl dithiocarbamates. The targets for developing the method included catalyst-free, base-free, mild reaction conditions, room temperature synthesis with high yields, and broad substrate scope. Apart from this, our approach is also helpful for synthesizing potentially bioactive compounds and drug modification. An antimicrobial assay and a docking study on dihydrofolate reductase (DHFR) and dihydropteroate synthase (DHPS) enzymes of the three synthetic derivatives were performed to evaluate the antimicrobial potency of the new compounds and thus inhibit the enzyme's action.

Graphical abstract: Metal-free, tert-butyl nitrite promoted C(sp2)–S coupling reaction: the synthesis of aryl dithiocarbamates and analysis of antimicrobial activity by ‘in silico’ and ‘in vitro’ methods for drug modification

Supplementary files

Article information

Article type
Paper
Submitted
22 Aug 2023
Accepted
25 Oct 2023
First published
25 Oct 2023

Green Chem., 2023,25, 9847-9856

Metal-free, tert-butyl nitrite promoted C(sp2)–S coupling reaction: the synthesis of aryl dithiocarbamates and analysis of antimicrobial activity by ‘in silico’ and ‘in vitro’ methods for drug modification

S. Pal, S. Sarkar, A. Mukherjee, A. Kundu, A. Sen, J. Rath, S. Santra, G. V. Zyryanov and A. Majee, Green Chem., 2023, 25, 9847 DOI: 10.1039/D3GC03153E

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