Affiliation:
1. Department of Physical Sciences, Chemistry Division, College of Science, Jazan University, P.O. Box 114, Jazan 45142, Saudi Arabia
Abstract
Carbothioamides 3a,b were generated in high yield by reacting furan imidazolyl ketone 1 with N-arylthiosemicarbazide in EtOH with a catalytic amount of conc. HCl. The reaction of carbothioamides 3a,b with hydrazonyl chlorides 4a–c in EtOH with triethylamine at reflux produced 1,3-thiazole derivatives 6a–f. In a different approach, the 1,3-thiazole derivatives 6b and 6e were produced by reacting 3a and 3b with chloroacetone to afford 8a and 8b, respectively, followed by diazotization with 4-methylbenzenediazonium chloride. The thiourea derivatives 3a and 3b then reacted with ethyl chloroacetate in ethanol with AcONa at reflux to give the thiazolidinone derivatives 10a and 10b. The produced compounds were tested for antioxidant and antibacterial properties. Using phosphomolybdate, promising thiazoles 3a and 6a showed the best antioxidant activities at 1962.48 and 2007.67 µgAAE/g dry samples, respectively. Thiazoles 3a and 8a had the highest antibacterial activity against S. aureus and E. coli with 28, 25 and 27, 28 mm, respectively. Thiazoles 3a and 6d had the best activity against C. albicans with 26 mm and 37 mm, respectively. Thiazole 6c had the highest activity against A. niger, surpassing cyclohexamide. Most compounds demonstrated lower MIC values than neomycin against E. coli, S. aureus and C. albicans. A molecular docking study examined how antimicrobial compounds interact with DNA gyrase B crystal structures. The study found that all of the compounds had good binding energy to the enzymes and reacted similarly to the native inhibitor with the target DNA gyrase B enzymes’ key amino acids.
Reference55 articles.
1. Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones;Narasimhan;J. Enzym. Inhib. Med. Chem.,2011
2. Pyrazole nucleus fused trisubstituted imidazole derivatives as antioxidant and antibacterial agents. Karbala;Brahmbhatt;Int. J. Mod. Sci.,2018
3. Synthesis of azolines and imidazoles and their use in drug design;Med. Chem.,2016
4. Studies on Imidazole and its derivatives with particular emphasis on their chemical/biological applications as bioactive molecules/intermediated to bioactive molecule;Kumar;Curr. Synth. Syst. Biol.,2017
5. Synthesis of imidazo[1,2-a]pyridines as antiviral agents;Gueiffier;J. Med. Chem.,1998
Cited by
3 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献