Deep Eutectic Solvent (DES)‐Mediated Green Approach for Synthesis of Benzothiazole Tethered Pyrazoles: Antimicrobial Properties and Molecular Docking Insights

Abstract The escalating incidence of bacterial resistance to commonly prescribed antibiotics underscores the urgent need for the rapid development of innovative antibacterial medications. Heterocyclic compounds, particularly nitrogen‐containing heterocycles like pyrazoles and thiazoles, have garnered attention for their diverse biological activities, including antimicrobial properties. Here, we present a green and efficient multicomponent synthesis method for fourteen novel benzothiazole‐tethered pyrazole derivatives. Utilizing the deep eutectic solvent glycerol/K 2 CO 3 as a base‐catalytic reaction medium at 70 °C, this synthesis approach yielded promising compounds exhibiting substantial antimicrobial activity against various pathogenic microorganisms such as Staphylococcus aureus , Bacillus cereus , and Candida albicans . Among these, 4‐(benzo[ d ]thiazol‐2‐yl)‐3‐(4‐nitrophenyl)‐1‐phenyl‐1 H ‐pyrazol‐5‐amine emerged as the most promising candidate, showcasing significant inhibitory potentials with CZD values of 24 mm, 21 mm, and 26 mm for S. aureus , B. cereus , and C. albicans , respectively. Molecular docking studies further supported the experimental observations, revealing the high binding affinity of the compound to the nitroreductase enzyme with a binding score of −8.5 kcal/mol. These findings underscore the potential of these synthesized compounds as antimicrobial agents and suggest avenues for future research in exploring their structure‐activity relationships and therapeutic applications in combating bacterial infections.

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Journal
ChemistrySelect
Published
2024-08-22
DOI
https://doi.org/10.1002/slct.202401009
Citations
1
Primary Topic
Synthesis and biological activity
Type
article
Field-Weighted Citation Impact
0.25

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article

Deep Eutectic Solvent (DES)‐Mediated Green Approach for Synthesis of Benzothiazole Tethered Pyrazoles: Antimicrobial Properties and Molecular Docking Insights

Essam M. Hussein, Hussein H. Abulreesh, Hatem M. Altass, Saleh A. Ahmed et al.
1 citations
ChemistrySelect
Synthesis and biological activity
0.25
article

Deep Eutectic Solvent (DES)‐Mediated Green Approach for Synthesis of Benzothiazole Tethered Pyrazoles: Antimicrobial Properties and Molecular Docking Insights

Essam M. Hussein, Hussein H. Abulreesh, Hatem M. Altass, Saleh A. Ahmed, Amrita Banerjee, Arpita Chattopadhyay, Rami J. Obaid, Meshal Almalki, Ahmad Abd‐El‐Aziz, Ziad Moussa, Samir Kumar Pal, Khaled Elbanna
article en
1 citations

Abstract

Abstract The escalating incidence of bacterial resistance to commonly prescribed antibiotics underscores the urgent need for the rapid development of innovative antibacterial medications. Heterocyclic compounds, particularly nitrogen‐containing heterocycles like pyrazoles and thiazoles, have garnered attention for their diverse biological activities, including antimicrobial properties. Here, we present a green and efficient multicomponent synthesis method for fourteen novel benzothiazole‐tethered pyrazole derivatives. Utilizing the deep eutectic solvent glycerol/K 2 CO 3 as a base‐catalytic reaction medium at 70 °C, this synthesis approach yielded promising compounds exhibiting substantial antimicrobial activity against various pathogenic microorganisms such as Staphylococcus aureus , Bacillus cereus , and Candida albicans . Among these, 4‐(benzo[ d ]thiazol‐2‐yl)‐3‐(4‐nitrophenyl)‐1‐phenyl‐1 H ‐pyrazol‐5‐amine emerged as the most promising candidate, showcasing significant inhibitory potentials with CZD values of 24 mm, 21 mm, and 26 mm for S. aureus , B. cereus , and C. albicans , respectively. Molecular docking studies further supported the experimental observations, revealing the high binding affinity of the compound to the nitroreductase enzyme with a binding score of −8.5 kcal/mol. These findings underscore the potential of these synthesized compounds as antimicrobial agents and suggest avenues for future research in exploring their structure‐activity relationships and therapeutic applications in combating bacterial infections.

ChemistrySelectVol. 9(32)
Harbin Engineering University (CN), Jadavpur University (IN), Umm al-Qura University (SA), United Arab Emirates University (AE), Fayoum University (EG), S.N. Bose National Centre for Basic Sciences (IN), Assiut University (EG)
United Arab Emirates University
Openalex Percentile: Top 49%
Synthesis and biological activity
0.25
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