1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity.

摘要: Versatile 1,2,3-triazole pharmacophore-based benzofused heterocycles containing halogen-substituted aromatic (9-17 and 25-28), 7-substituted coumarin (18-23 29-30) or penciclovir-like subunit (31a,b-38a) were designed synthesized to evaluate their antibacterial activities against selected Gram-positive Gram-negative bacteria. Hybridization approach using environmentally friendly Cu(I)-catalyzed click reaction under microwave irradiation was adopted in the synthesis of regioselective 1,4-disubstituted tethered (9-23 25-30), while post-N-alkylation NH-1,2,3-triazoles afforded both 2,4- (31a-38a) (31b-33b, 35b-37b) regioisomers. The compounds 18-23 25-30 revealed fluorescence violet region visible spectrum with a strong influence phenyl spacer on wavelength emission intensity. Fusion subunits led new hybrid architecture, benzothiazole-1,2,3-triazole-coumarin 29 that demonstrated extremely narrow activity towards fastidious bacteria Moraxella catarrhalis. Selected showed potency catarrhalis (MIC⩽0.25μg/mL) comparable reference antibiotic azithromycin, which suggested further investigations are necessary optimize this potential hit compound as anti-Moraxella agent.