New Methionine-based P-toluenesulphonamoyl Carboxamide Derivatives as Antimicrobial and Antioxidant Agents: Design, Synthesis and Molecular Docking
Melford Chuka Egbujor, Uchechukwu Chris Okoro
Journal of Pharmaceutical Research International · pp. 1–12 · Published 13 Jun 2019
10.9734/jpri/2019/v28i130192Abstract
Aim: The reported emergence of drug resistant microbes and the prevalence of oxidative stress related diseases prompted the need for the development of new antimicrobial and antioxidant agents. The synthesis of methione-based sulphonamoyl carboxamides bearing aniline, pyridine and pyrimidine pharmacophores is reported. Place and duration: Department of Industrial Chemistry, Renaissance University, Ugbawka, Enugu, 2018. Methodology: The p-toluenesulphonyl chloride reaction with methionine gave compound 3a which was acylated to afford compound 3b. Further chlorination and aminolysis of compound 3b gave the carboxamide (3c). Nickel catalysed reaction of the carboxamide with aryl/heteroaryl halides afforded compounds 3d-f in excellent yields. Characterization of compounds was done using H1-NMR, C13-NMR, FTIR and elemental analysis. Their antimicrobial, antioxidant activity and molecular docking were determined. Results: Compounds 3a and 3e had the best antimicrobial activity with minimum inhibitory concentration (MIC) in the range of 0.6 – 0.9mg/ml and the highest antioxidant percentage inhibition (93.53% and 93.28% at 200µg/ml respectively) comparable with ascorbic acid (96.83% at 200µg/ml) and also the best IC50 values of 1.031 and 1.051µg/ml. The molecular docking study, revealed that compounds 3a (TPSA = 83.47 Å2) could permeate blood-brain barriers. Compound 3e (-11.14 kcal/mol) had a better in silico antibacterial activity than penicillin (-10.89 kcal/mol) while compound 3a (-14.90kcal/mol) had a better antioxidant activity than α-tocopherol (-14.82 kcal/mol). Conclusion: All the synthesized compounds were confirmed to be likely drugs and potential antimicrobial and antioxidant, agents.
References (12)
- 1 Antioxidant Determinations by the Use of a Stable Free Radical [DOI]
- 2 Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances [DOI]
- 3 Oxidative Stress: Harms and Benefits for Human Health [DOI]
- 4 Amide bond formation and peptide coupling [DOI]
- 5 Oxidative stress and cancer: have we moved forward? [DOI]
- 6 Toxicity and metabolism of industrial solvents [DOI]
- 7 Synthesis of Essential Drugs [DOI]
- 8 Novel approaches to developing new antibiotics for bacterial infections [DOI]
- 9 Sulfur-Nitrogen Heterocycles [DOI]
- 10 STI-571: an anticancer protein-tyrosine kinase inhibitor [DOI]
- 11 Anti-infective research and development—problems, challenges, and solutions [DOI]
- 12 Concerted Antibiotic Effect of Penicillin, Methionine, Threonine and Methionine Sulfoxide Upon Brucella, Eberthella, Salmonella, and Shigella [DOI]
Cited by 25
A. D. Jacob, U. C. Okoro, A. J. Dauda · Recent Advances in Natural Sciences · 2024
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Melford Chuka Egbujor, Brigitta Buttari, Elisabetta Profumo · International Journal of Molecular Sciences · 2022
Jacob Alifa David, Uchechukwu Chris Okoro, Dauda Abiodun Joseph · 2025
Melford Chuka Egbujor, Maria Petrosino, Karim Zuhra · Antioxidants · 2022
Melford C. Egbujor, Olugbemi T. Olaniyan, Chigbundu N. Emeruwa · Amino Acids · 2024
Melford Chuka Egbujor · Central Nervous System Agents in Medicinal Chemistry · 2024
Noha H. Amin, Mohammed T. Elsaadi, Shimaa S. Zaki · Bioorganic Chemistry · 2020
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