Synthesis and Antimicrobial Activity Evaluation of Homodrimane Sesquiterpenoids with a Benzimidazole Unit
Lidia Lungu,
Svetlana Blaja,
Caleria Cucicova,
Alexandru Ciocarlan,
Alic Barba,
Veaceslav Kulcițki,
Sergiu Shova,
Nicoleta Vornicu,
Elisabeta-Irina Geana,
Ionel I. Mangalagiu,
Aculina Aricu
Affiliations
Lidia Lungu
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., 2028 Chisinau, Moldova
Svetlana Blaja
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., 2028 Chisinau, Moldova
Caleria Cucicova
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., 2028 Chisinau, Moldova
Alexandru Ciocarlan
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., 2028 Chisinau, Moldova
Alic Barba
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., 2028 Chisinau, Moldova
Veaceslav Kulcițki
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., 2028 Chisinau, Moldova
Sergiu Shova
“Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41-A, 700487 Iasi, Romania
Nicoleta Vornicu
Metropolitan Center of Research T.A.B.O.R., 9 Closca Str., 700066 Iasi, Romania
Elisabeta-Irina Geana
Department of Research and Development, National Research and Development Institute for Cryogenics and Isotopic Technologies—ICSI Rm., Valcea, 4th Uzinei Str., 240050 Râmnicu Vâlcea, Romania
Ionel I. Mangalagiu
Faculty of Chemistry, “Alexandru Ioan Cuza” University of Iasi, 11 Carol Bd., 700506 Iasi, Romania
Aculina Aricu
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., 2028 Chisinau, Moldova
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.
