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Synthesis 2024; 56(03): 469-481
DOI: 10.1055/a-2193-5436
paper

An Efficient Copper-Mediated Route for the Synthesis of 2-Substituted Benzothiazoles from Dithioesters and Investigation of Their Antibacterial Activities

Kodipura P. Sukrutha
a   Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570006, India
,
Kuppalli R. Kiran
a   Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570006, India
,
Kodagahally T. Gunashree
a   Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570006, India
,
Shivakumar Divyashree
b   Department of Studies in Microbiology, University of Mysore, Manasagangothri, Mysuru, 570006, India
,
Prerana Purusotham
b   Department of Studies in Microbiology, University of Mysore, Manasagangothri, Mysuru, 570006, India
,
Marikunte Y. Sreenivasa
b   Department of Studies in Microbiology, University of Mysore, Manasagangothri, Mysuru, 570006, India
,
Maralinganadoddi P. Sadashiva  ∗
a   Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysuru, 570006, India
› Author AffiliationsK.P.S. thanks the Institute of Excellence, University of Mysore, Mysuru for providing a fellowship to conduct research and an instrumentation facility [IOE PROJECT: DV 2/30/PDF/PA/IOE/2010-11 (VOL-II) Dated 16.10.2019]. The authors thank the Vision Group on Science and Technology (VGST) Government of Karnataka for the project VGST-K-FIST L1, GRD NO:1038/2021-22/427e.
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Abstract

An efficient one-pot synthesis of 2-aryl/2-aroylbenzothiazoles through copper-mediated condensation of 2-chloroanilines with dithioesters has been developed. The method provides good isolated yields and exhibits broad functional group tolerance, accommodating both electron-donating and electron-withdrawing groups on the substrates. A series of synthesized compounds was evaluated for their antibacterial activity against Klebsiella pneumoniae, Pseudomonas aeruginosa, and Salmonella paratyphi. Among the series, three compounds exhibited a significant inhibitory effect against the tested pathogens, with one also demonstrating potential as an effective compound in both the agar well diffusion assay and broth microdilution assay. Additionally, the three compounds displayed strong inhibitory effects on biofilm formation of the pathogens in both the crystal violet assay and MTT assay at a concentration of 10 mM. These findings highlight the promising antimicrobial and antibiofilm properties of these compounds, indicating the potential for their further investigation as potential therapeutic agents against the tested pathogens.

Key words

dithioesters - 2-chloroanilines - benzothiazoles - cyclization - antimicrobial activities

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2193-5436.
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Publication History

Received: 08 September 2023

Accepted after revision: 17 October 2023

Accepted Manuscript online:
17 October 2023

Article published online:
22 November 2023

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