1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity (CROSBI ID 222463)
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Podaci o odgovornosti
Maračić, Silvija ; Gazivoda Kraljević, Tatjana ; Čipčić Paljetak, Hana ; Perić, Mihaela ; Matijašić, Mario ; Verbanac, Donatella ; Cetina, Mario ; Raić-Malić, Silvana
engleski
1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity
Versatile 1, 2, 3-triazole pharmacophore-based benzofused heterocycles containing halogen- substituted aromatic (9–17 and 25–28), 7- substituted coumarin (18–23 and 29–30) or penciclovir-like subunit(31a, b–38a) were designed and synthesized to evaluate their antibacterial activities against selected Gram- positive and 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 1, 2, 3-triazole tethered heterocycles (9–23 and 25–30), while post-N- alkylation of NH- 1, 2, 3-triazoles afforded both 2, 4- (31a–38a) and 1, 4-disubstituted (31b–33b, 35b–37b) 1, 2, 3- triazole regioisomers. The compounds 18–23 and 25– 30 revealed fluorescence in the violet region of the visible spectrum with a strong influence of phenyl spacer in 25–30 on both wavelength and emission intensity. Fusion of selected subunits led to new hybrid architecture, benzothiazole– 1, 2, 3-triazole– coumarin 29 that demonstrated extremely narrow spectrum activity towards fastidious Gram- negative bacteria Moraxella catarrhalis. Selected hybrid showed the potency against Moraxella catarrhalis (MIC < 0.25 ug/mL) comparable to that of reference antibiotic azithromycin, which suggested that further investigations are necessary to optimize this potential hit compound as a new anti-Moraxella catarrhalis agent.
1, 2, 3-Triazole ; coumarin ; hybridization approach ; fluorescence ; antibacterial activity ; Moraxella catarrhalis
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Podaci o izdanju
23 (23)
2015.
7448-7463
objavljeno
0968-0896
1464-3391
10.1016/j.bmc.2015.10.042