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

doi:10.3390/molecules27165082

Molecules (Aug 2022)

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

DOI: https://doi.org/10.3390/molecules27165082
Journal volume & issue: Vol. 27, no. 16
p. 5082

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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