Synthesis and Antimicrobial Activity Evaluation of Homodrimane Sesquiterpenoids with a Benzimidazole Unit

Autor: Lidia Lungu, Svetlana Blaja, Caleria Cucicova, Alexandru Ciocarlan, Alic Barba, Veaceslav Kulcițki, Sergiu Shova, Nicoleta Vornicu, Elisabeta-Irina Geana, Ionel I. Mangalagiu, Aculina Aricu
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Molecules, Vol 28, Iss 3, p 933 (2023)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules28030933
Popis: Herein we report a feasible study concerning the synthesis and the in vitro antimicrobial activity of some new homodrimane sesquiterpenoids with a benzimidazole unit. Based on some homodrimane carboxylic acids, on their acyl chlorides and intermediate monoamides, a series of seven N-homodrimenoyl-2-amino-1,3-benzimidazoles and 2-homodrimenyl-1,3-benzimidazoles was synthesized. The syntheses involved the decarboxylative cyclization and condensation of the said acids or acyl chlorides with o-phenylendiamine and 2-aminobenzimidazole, as well as the p-TsOH-mediated cyclodehydration of the said monoacylamides. The structures of the synthesized compounds have been fully confirmed, including by the X-ray diffraction. Their biological activities were evaluated on five species of fungi (Aspergillus niger, Fusarium solani, Penicillium chrysogenum, P. frequentans, and Alternaria alternata) and two strains of bacteria (Bacillus sp. and Pseudomonas aeruginosa). Compounds 7 and 20 showed higher antifungal (MIC = 0.064 and 0.05 μg/mL) and antibacterial (MIC = 0.05 and 0.032 μg/mL) activities compared to those of the standards: caspofungin (MIC = 0.32 μg/mL) and kanamycin (MIC = 2.0 μg/mL), and compounds 4, 10, 14, and 19 had moderate activities.
Databáze: Directory of Open Access Journals
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