Benzimidazole-1,2,3-triazole Hybrid Molecules: Synthesis and Evaluation for Antibacterial/Antifungal Activity

• Published in: Archiv der Pharmazie (Weinheim) Vol. 347; no. 10; pp. 748 - 755
• Main Authors: Ouahrouch, Abdelaaziz, Ighachane, Hana, Taourirte, Moha, Engels, Joachim W., Sedra, My Hassan, Lazrek, Hassan B.
• Format: Journal Article
• Language: English; German
• Published: WEINHEIM Blackwell Publishing Ltd 01.10.2014; Wiley; Wiley Subscription Services, Inc
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Antibacterial activity; Antifungal activity; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Bacteriology; Benzimidazoles - chemical synthesis; Benzimidazoles - pharmacology; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Drug Design; Fusarium - drug effects; Fusarium - growth & development; Gram-Negative Bacteria - drug effects; Gram-Negative Bacteria - growth & development; Gram-Positive Bacteria - drug effects; Gram-Positive Bacteria - growth & development; Hybrid molecules; Life Sciences & Biomedicine; Microbial Sensitivity Tests; Molecular Structure; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Structure-Activity Relationship; Triazoles - chemical synthesis; Triazoles - pharmacology; Verticillium - drug effects; Verticillium - growth & development; Antifungal activity; DESIGN; TOPOISOMERASE-II; MITOXANTRONE; INTERCALATION COMPLEXES; AMSACRINE; DRUGS; Antibacterial activity; DNA-INTERCALATION; ANTITUMOR; Hybrid molecules
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.201400142

A novel series of hybrid molecules 4a–i and 5a–i were prepared by condensation of 4‐(trimethylsilylethynyl)benzaldehyde 1 with substituted o‐phenylenediamines. These in turn were reacted with 2‐(azidomethoxy)ethyl acetate in a Cu alkyne–azide cycloaddition (CuAAC) to generate the 1,2,3‐triazole pharmacophore under microwave assistance. The newly synthesized compounds were examined for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and the phytopathogenic fungi Verticillium dahliae and Fusarium oxysporum f. sp. albedinis. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)methoxy)ethanol 5e showed a moderate inhibition of 30% in the Foa sporulation test. Hybrid molecules including benzimidazole, benzene, and triazole rings were synthesized and characterized. The compounds were assessed for their in vitro antimicrobial activities against Gram‐positive and Gram‐negative bacteria and phytopathogenic fungi. 2‐((4‐(4‐(5‐Trifluoromethyl benzimidazol‐2‐yl)phenyl)‐1,2,3‐triazol‐1‐yl)‐methoxy)ethanol 5e was found to achieve moderate inhibition of 30% in the Foa sporulation test.