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Article

Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT

by
Waseem Nazeer
1,
Muhammad Usman Qamar
2,3,
Nasir Rasool
1,*,
Mohamed Taibi
4 and
Ahmad Mohammad Salamatullah
5
1
Department of Chemistry, Government College University, Faisalabad 38000, Pakistan
2
Institute of Microbiology, Government College University, Faisalabad 38000, Pakistan
3
Division of Infectious Disease, Department of Medicine, University of Geneva, 1206 Geneva, Switzerland
4
Laboratory of Therapeutic and Organic Chemistry, Faculty of Pharmacy, University of Montpellier, 34000 Montpellier, France
5
Department of Food Science and Nutrition, College of Food and Agricultural Sciences, King Saud University, P.O. Box 2460, Riyadh 11451, Saudi Arabia
*
Author to whom correspondence should be addressed.
Submission received: 17 April 2024 / Revised: 10 June 2024 / Accepted: 10 June 2024 / Published: 25 June 2024

Abstract

A new class of thiophene-based molecules of 5-bromothiophene-2-carboxylic acid (1) have been synthesized in current research work. All analogs 4A–4G were synthesized with optimized conditions by coupling reactions of 2-ethylhexyl 5-bromothiophene-2-carboxylate (3) with various arylboronic acids. The results indicated that the majority of compounds showed promising effective in vitro antibacterial activity. Herein, 2-ethylhexyl-5-(p-tolyl)thiophene-2-carboxylate (4F), in particular among the synthesized analogs, showed outstanding antibacterial action (MIC value 3.125 mg/mL) against XDR Salmonella Typhi compared to ciprofloxacin and ceftriaxone. The intermolecular interaction was investigated by using a molecular docking study of thiophene derivatives 4A–4G against XDR S. Typhi. The values of the binding affinity of functionalized thiophene molecules and ciprofloxacin were compared against bacterial enzyme PDB ID: 5ztj. Therefore, 4F appears to be a promising antibacterial agent and showed the highest potential value. Density functional theory (DFT) calculations were executed to examine the electronic, structural, and spectroscopic features of the newly synthesized molecules 4A–4G.
Keywords: 2-ethylhexyl 5-bromothiophene-2-carboxylate; Suzuki; XDR Salmonella Typhi; antibacterial; molecular docking; density functional theory 2-ethylhexyl 5-bromothiophene-2-carboxylate; Suzuki; XDR Salmonella Typhi; antibacterial; molecular docking; density functional theory

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MDPI and ACS Style

Nazeer, W.; Qamar, M.U.; Rasool, N.; Taibi, M.; Salamatullah, A.M. Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT. Molecules 2024, 29, 3005. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29133005

AMA Style

Nazeer W, Qamar MU, Rasool N, Taibi M, Salamatullah AM. Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT. Molecules. 2024; 29(13):3005. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29133005

Chicago/Turabian Style

Nazeer, Waseem, Muhammad Usman Qamar, Nasir Rasool, Mohamed Taibi, and Ahmad Mohammad Salamatullah. 2024. "Synthesis of 2-Ethylhexyl 5-Bromothiophene-2-Carboxylates; Antibacterial Activities against Salmonella Typhi, Validation via Docking Studies, Pharmacokinetics, and Structural Features Determination through DFT" Molecules 29, no. 13: 3005. https://0-doi-org.brum.beds.ac.uk/10.3390/molecules29133005

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