Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
Lidia Lungu,
Caleria Cucicova,
Svetlana Blaja,
Alexandru Ciocarlan,
Ion Dragalin,
Alic Barba,
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., MD-2028 Chisinau, Moldova
Caleria Cucicova
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., MD-2028 Chisinau, Moldova
Svetlana Blaja
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., MD-2028 Chisinau, Moldova
Alexandru Ciocarlan
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., MD-2028 Chisinau, Moldova
Ion Dragalin
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., MD-2028 Chisinau, Moldova
Alic Barba
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., MD-2028 Chisinau, Moldova
Nicoleta Vornicu
Metropolitan Center of Research T.A.B.O.R., 9 Closca Str., RO-700066 Iasi, Romania
Elisabeta-Irina Geana
National Research and Development Institute for Cryogenics and Isotopic Technologies—ICSI Rm. Valcea, 4th Uzinei Str., P.O. Box 7, 240050 Ramnicu Valcea, Romania
Ionel I. Mangalagiu
Faculty of Chemistry, ‘‘Alexandru Ioan Cuza’’ University of Iasi, 11 Carol Bd., RO-700506 Iasi, Romania
Aculina Aricu
Chemistry of Natural and Biologically Active Compounds Laboratory, Institute of Chemistry, 3 Academiei Str., MD-2028 Chisinau, Moldova
Based on some homodrimane carboxylic acids and their acyl chlorides, a series of fourteen 2-homodrimenyl-1,3-benzothiazoles, N-homodrimenoyl-2-amino-1,3-benzothiazoles, 4′-methyl-homodrimenoyl anilides and 4′-methyl-homodrimenthioyl anilides were synthesized and 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). The synthesis involved the decarboxylative cyclization, condensation and thionation of the said acids, anhydrides or their derivatives with 2-aminothiophenol, 2-aminobenzothiazole, p-toluidine and Lawesson’s reagent. As a result, together with the desired compounds, some unexpected products 8, 25, and 27 were obtained, and the structures and mechanisms for their formation have been proposed. Compounds 4, 9, and 25 showed higher antifungal and antibacterial activity compared to the standards caspofungin (MIC = 1.5 μg/mL) and kanamycin (MIC = 3.0 μg/mL), while compound 8 had comparable activities. In addition, compounds 6, 17, and 27 showed selective antifungal activity at MIC = 2.0, 0.25, and 1.0 μg/mL, respectively.
