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

Autori
Maračić, Silvija ; Gazivoda Kraljević, Tatjana ; Čipčić Paljetak, Hana ; Perić, Mihaela ; Matijašić, Mario ; Verbanac, Donatella ; Cetina, Mario ; Raić-Malić, Silvana

Izvornik
Bioorganic & medicinal chemistry (0968-0896) 23 (2015), 23; 7448-7463

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
1, 2, 3-Triazole ; coumarin ; hybridization approach ; fluorescence ; antibacterial activity ; Moraxella catarrhalis

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA