Synthesis of sustainable heterocyclic aryl sulfonamide derivatives: computational studies, molecular docking, and antibacterial assessment


Kumar A., Masroor S., BATIR G. G., Katin K. P., Berisha A., Khan M. E., ...Daha Fazla

Macromolecular Research, 2024 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1007/s13233-024-00335-w
  • Dergi Adı: Macromolecular Research
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Compendex, INSPEC
  • Anahtar Kelimeler: Antibacterial assessment, Computational studies, Molecular docking, Sustainable synthesis, Thiophene containing p-toluene sulfonamide
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

The treatment of infectious diseases is impacted by the emergence of multidrug-resistant microbiological infections. Due to the long-term usage of antibacterial clinical drugs, microbes develop resistance to clinical drugs. To take advantage of the potential of these families of chemicals, several derivatives of thiophene containing p-toluene sulfonamide (TPS) were prepared using an eco-friendly method with high yields. These synthetic derivatives had a wide range of structural diversity to demonstrate a structure–activity link. In multi-component reaction (MCR), the versatile reactants (1 mmol) react for up to 6–8 h at pH 7.2 ± 0.2 and temperature 70 ± 1 °C. The reaction involved the reusable organic catalyst l-Proline (1 mol%), and the mechanisms through a Knoevenagel condensation pathway, which has the advantage of effectively producing the described thiophene derivatives (TD). Then, further TD reacts with p-toluene sulfonamide (Tosyl-Cl) at 0 °C within 10–12 h to provide the final product TPS. The present investigation provides an inexpensive and eco-friendly method of TPS derivatives. A perusal of the tables indicates that TPS derivatives exhibited promising activity against S. typhimurium as compared to E. coli and S. aureus. The compounds having good activity contained electron-withdrawing as well as electron-donating substituent groups on the benzaldehyde benzene ring of the amino part of the amide. Graphical abstract: (Figure presented.)