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Antimicrobial Evaluation of a Set of Heterobicyclic Methylthiadiazole Hydrazones: Synthesis, Characterization, and SAR Studies

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journal contribution
posted on 11.12.2013, 00:00 by Paulrasu Kodisundaram, Shanmugasundaram Amirthaganesan, Thirunavukkarasu Balasankar
To exploit the potential antimicrobial activities of azabicyclic skeleton based compounds, a set of 2r,4c-diaryl-3-azabicyclo[3.3.1]­nonan-9-one-4-methyl-1,2,3-thiadazole-5-carbonyl hydrazones were synthesized. Unambiguous structural elucidation has been carried out by investigating IR, H1, C13 NMR, and elemental analysis. 2D NMR spectra (1H–1H COSY, HSQC, HMBC, and NOESY) were recorded for a representative compound, 12, to confirm the proposed structure for 915. Antimicrobial activity assessment of synthesized hydrazones 915 has been evaluated by screening against selective strains. Both bacteria and fungi of various forms along with standard drug have been taken for the analysis. Difference in the potency of activity against the strains has been evaluated on the basis of SAR, and it has been revealed that substitution of electron-withdrawing halogens (chloro, fluoro, and bromo) at para positions of the phenyl (10, 12, and 13) enhanced the antifungal and antibacterial activities against tested organisms compared to other hydrazone derivatives.