Skip to content
Research Article Open access CC BY 4.0

Design, Synthesis, Antimicrobial and Antioxidant Activities of Novel Threonine-based Sulfonamide Derivatives

M. C. Egbujor, U. C. Okoro, D. C. Nwobodo, C. U. Ezeagu, U. B. Amadi, C. G. Okenwa-Ani, J. I. Ugwu, I. G. Okoye, I. P. Abu, P. I. Egwuatu

Journal of Pharmaceutical Research International · pp. 51–61 · Published 30 May 2020

10.9734/jpri/2020/v32i830470

Abstract

Aim: To systematically design, synthesize and evaluate the biological activities of new threonine-based sulfonamide derivatives in order to achieve improved drug potency. Methodology: Sulfamoyl carboxylic acids were prepared by the reaction of threonine with the appropriate sulfonyl chloride while their acetylated, carboxamide and aniline derivatives were synthesized via Lumiere-Barbier acetylation, Schotten-Baumann ammonolysis and Buchwald-Hartwig cross-coupling methods respectively. The FTIR, 1H-NMR, 13C-NMR and elemental analytical data were employed in the structural characterization. In vitro and in silico antioxidant and antimicrobial studies were carried out. Results: Compounds 1b and 1d displayed the best in vitro antibacterial activities against Escherichia coli, Salmonella typhi, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and antifungal activities against Candida albican sand Aspergillus niger. Compound 1f (IC50 = 1.150±0.003 µg/ml) exhibited the best in vitro antioxidant activity. Compound 1a had a higherin silico antibacterial (-11.51 kcal/mol) binding energies than antibacterial reference drug, penicillin (-10.89 kcal/mol). Compound 1c had the highest in silico antifungal binding energy (-10.48 kcal/mol)comparable to ketoconazole (-10.85 kcal/mol). Conclusion: All the compounds were found to be potential antioxidant and antimicrobial drug candidates having complied with Lipinski’s rule of five.

Threonine sulfonamides In silico antimicrobial antioxidant

References (14)

  1. 1 Global and regional mortality from 235 causes of death for 20 age groups in 1990 and 2010: a systematic analysis for the Global Burden of Disease Study 2010 [DOI]
  2. 2 Agar and broth dilution methods to determine the minimal inhibitory concentration (MIC) of antimicrobial substances [DOI]
  3. 3 Oxidative stress and cancer: have we moved forward? [DOI]
  4. 4 Novel approaches to developing new antibiotics for bacterial infections [DOI]
  5. 5 Adult Amino Acid Requirements: The Case for a Major Revision in Current Recommendations [DOI]
  6. 6 Sorghum: An Underutilized Cereal Whole Grain with the Potential to Assist in the Prevention of Chronic Disease [DOI]
  7. 7 Inhibition of HIV‐1 Replication by Isoxazolidine and Isoxazole Sulfonamides [DOI]
  8. 8 Biocompatibility and antibacterial activity of photolytic products of sulfonamides [DOI]
  9. 9 Supercritical carbon dioxide extraction of xanthones with antioxidant activity from Garcinia mangostana: Characterization by HPLC/LC–ESI-MS [DOI]
  10. 10 Potential Of Seaweed Padina Sp. As A Source Of Antioxidant
  11. 11 Understanding the importance of glycosylated threonine and stereospecific action of Drosocin, a Proline rich antimicrobial peptide [DOI]
  12. 12 The infectious disease challenges of our time [DOI]
  13. 13 Emerging and reemerging pathogens [DOI]
  14. 14 Effects of dietary L-threonine levels on antioxidant capacity, digestive enzyme activities, and antibody production of Xinyang green-shell laying hens [DOI]

Cited by 24

Sulfonamide a Valid Scaffold for Antioxidant Drug Development

Melford Chuka Egbujor, Jorge Garrido, Fernanda Borges · Mini-Reviews in Organic Chemistry · 2023

Design, Synthesis, Molecular docking and Biological Evaluation of Novel Leucine Derived Sulfamoyl Pentanamides as Antimicrobial and Antioxidant Agents

Melford Egbujor, Vivian Okonkwo, Ugomma Onyeije · Jordan Journal of Pharmaceutical Sciences · 2024

An Overview of NRF2-Activating Compounds Bearing α,β-Unsaturated Moiety and Their Antioxidant Effects

Melford Chuka Egbujor, Brigitta Buttari, Elisabetta Profumo · International Journal of Molecular Sciences · 2022

The Role of Organosulfur Compounds as Nrf2 Activators and Their Antioxidant Effects

Melford Chuka Egbujor, Maria Petrosino, Karim Zuhra · Antioxidants · 2022

An insight into role of amino acids as antioxidants via NRF2 activation

Melford C. Egbujor, Olugbemi T. Olaniyan, Chigbundu N. Emeruwa · Amino Acids · 2024

Drug Repurposing Approach in Developing New Furosemide Analogs as Antimicrobial Candidates and Anti-PBP: Design, Synthesis, and Molecular Docking

Marwa F. Harras, Rehab Sabour, Thoraya A. Farghaly · Bioorganic Chemistry · 2023

Sulfonamides: a versatile scaffold for diverse biological activity

Samiksha J. Kokre, Rohini S. Kavalapure, Sushmitha S. Huddi · Results in Chemistry · 2025

Phenothiazines: Nrf2 activation and antioxidant effects

Melford C. Egbujor, Paolo Tucci, Brigitta Buttari · Journal of Biochemical and Molecular Toxicology · 2024

Synthesis, Molecular Docking, and Peroxidase Modulatory Activity of Novel Sulphonamide-Functionalised Aspartic Acid Carboxamides

Uwem Godswill Uduak, Kingsley Nnemeka Okah, Ozoemena Emmanuel Eje · 2026

Bioactive Sulfonamides Derived from Amino Acids: Their Synthesis and Pharmacological Activities

Melford Chuka Egbujor, Paolo Tucci, Luciano Saso · Mini-Reviews in Medicinal Chemistry · 2025

Showing 10 of 24 known citations — external sources report more than can currently be individually listed.

Related research

Article metrics

Real usage data collected on this platform.

20

Page views

0

PDF downloads

4

Outbound clicks

24

Citations

Views over time

Views by country

Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".

Traffic sources

Referring site, by host.

Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.