Affiliation:
1. Department of Chemistry Gayatri Vidya Parishad College of Engineering (Autonomous) Visakhapatnam Andhra Pradesh India
2. Department of Chemistry National Institute of Technology Calicut Calicut Kerala India
3. Department of Chemistry, School of Sciences National Institute of Technology Andhra Pradesh Tadepalligudem Andhra Pradesh India
4. Department of Chemical Engineering Gayatri Vidya Parishad College of Engineering (Autonomous) Visakhapatnam Andhra Pradesh India
Abstract
ABSTRACTAntimicrobial resistance is one of the biggest threats to public health across the globe. Bacteria, fungi, viruses, and protozoans have been exhibiting resistance against antimicrobial drugs making them ineffective. Hence, the development of new antibiotics with a different mode of action is highly desirable. In this study, 10 new chromone‐incorporated fused thiazolo[2,3‐b]quinazolinone derivatives, 8a‐j, have been prepared via Biginelli reaction involving aromatic aldehydes, 1‐tetralone, and thiourea followed by a reaction with 2‐chloro‐N‐phenylacetamide, and Knoevenagel condensation with 3‐formylchromone. All the structures of the compounds were characterized by NMR, FTIR, and mass spectrometry. The in vitro antibacterial activities of all the synthesized compounds against the four different microbial strains were evaluated. Among them, few compounds demonstrated prominent activity against Staphylococcus aureus, Streptococcus pyogenes, and Pseudomonas aeruginosa. No appreciable activity of any compound against Klebsiella pneumoniae was observed. Molecular docking studies were employed to reveal the interactions responsible for the potent compounds' activities against S. aureus, S. pyogenes, and P. aeruginosa. Both in vitro and in silico studies have been carried out by using standard agar well diffusion protocol and Auto Dock Vina in PyRx. The results indicated that compound 8c was the potential compound as it showed good affinity toward the receptors of all three organisms. Molecular dynamics simulation of the 8c‐1JIJ complex for 100 ns further confirmed the potentiality of 8c. The pharmacokinetic properties of the compounds indicate that the studied molecules have exhibited a favorable profile.
Reference58 articles.
1. One Pot Synthesis of Thiazolodihydropyrimidinones and Evaluation of Their Anticancer Activity;Holla B. S.;European Journal of Medicinal Chemistry,2004
2. Design, Synthesis and Antibacterial Activity of Novel 7H‐Thiazolo[3,2‐b]‐1,2,4‐Triazin‐7‐One Derivatives;Hou S.;Heliyon,2024
3. Design and Synthesis of Some Substituted Thiazolo[3,2‐a]Pyrimidine Derivatives of Potential Biological Activities;Moty S. G. A.;Saudi Pharmaceutical Journal,2016
4. One Pot Synthesis of Thiazolo[2,3‐B]Dihydropyrimidinone Possessing Pyrazole Moiety and Evaluation of Their Anti‐Inflammatory and Antimicrobial Activities;Viveka S.;Medicinal Chemistry Research,2018
5. Thiazolidione Derivatives as Novel Antibiofilm Agents: Design, Synthesis, Biological Evaluation, and Structure–Activity Relationships;Pan B.;European Journal of Medicinal Chemistry,2011