Synthesis and biological evaluation of novel benzenesulfonamide incorporated thiazole-triazole hybrids as antimicrobial and antioxidant agents

A library of 20 novel benzenesulfonamide incorporating thiazole tethered 1,2,3-triazoles 1-4a-e was synthesized and screened for their antimicrobial, antioxidant, and cytotoxicity studies. Amoxicillin and fluconazole were used as reference antibacterial and antifungal drugs, respectively. Further, energies of frontier molecular orbitals were calculated for all the synthesized target compounds 1-4a-e to correlate electronic parameters with the observed biological results. Global reactivity descriptors, including highest occupied molecular orbitals-lowest unoccupied molecular orbitals energy gap, electronegativity, chemical hardness, chemical softness, and electrophilicity index, were also calculated for the synthesized molecules. All the tested compounds possessed moderate to excellent antibacterial potency; however, 3d and 4d exhibited the overall highest antibacterial effect (minimum inhibitory concentration [MIC] values 5-11 mu M) while 2c showed the highest antifungal effect (MIC value 6 mu M). Compound 3c exhibited the highest antioxidant activity with a % radical scavenging activity value of 95.12. The cytotoxicity of the compounds 1-4a-e was also checked against an animal cell line and a plant seed germination cell line, and the compounds were found to be safe against both the tested cell lines. A series of nontoxic benzenesulfonamide-containing thiazole-triazole hybrids was synthesized and analyzed for antimicrobial and antioxidant activities. The compounds possessed good to excellent antimicrobial and antioxidant profiles. The observed biological profile was further justified by the results of density functional theory studies.image