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Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation

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 eval...

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Autores principales: Lungu, Lidia, Cucicova, Caleria, Blaja, Svetlana, Ciocarlan, Alexandru, Dragalin, Ion, Barba, Alic, Vornicu, Nicoleta, Geana, Elisabeta-Irina, Mangalagiu, Ionel I., Aricu, Aculina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414590/
https://www.ncbi.nlm.nih.gov/pubmed/36014322
http://dx.doi.org/10.3390/molecules27165082
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author Lungu, Lidia
Cucicova, Caleria
Blaja, Svetlana
Ciocarlan, Alexandru
Dragalin, Ion
Barba, Alic
Vornicu, Nicoleta
Geana, Elisabeta-Irina
Mangalagiu, Ionel I.
Aricu, Aculina
author_facet Lungu, Lidia
Cucicova, Caleria
Blaja, Svetlana
Ciocarlan, Alexandru
Dragalin, Ion
Barba, Alic
Vornicu, Nicoleta
Geana, Elisabeta-Irina
Mangalagiu, Ionel I.
Aricu, Aculina
author_sort Lungu, Lidia
collection PubMed
description 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.
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spelling pubmed-94145902022-08-27 Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation Lungu, Lidia Cucicova, Caleria Blaja, Svetlana Ciocarlan, Alexandru Dragalin, Ion Barba, Alic Vornicu, Nicoleta Geana, Elisabeta-Irina Mangalagiu, Ionel I. Aricu, Aculina Molecules Article 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. MDPI 2022-08-10 /pmc/articles/PMC9414590/ /pubmed/36014322 http://dx.doi.org/10.3390/molecules27165082 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Lungu, Lidia
Cucicova, Caleria
Blaja, Svetlana
Ciocarlan, Alexandru
Dragalin, Ion
Barba, Alic
Vornicu, Nicoleta
Geana, Elisabeta-Irina
Mangalagiu, Ionel I.
Aricu, Aculina
Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
title Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
title_full Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
title_fullStr Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
title_full_unstemmed Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
title_short Synthesis of Homodrimane Sesquiterpenoids Bearing 1,3-Benzothiazole Unit and Their Antimicrobial Activity Evaluation
title_sort synthesis of homodrimane sesquiterpenoids bearing 1,3-benzothiazole unit and their antimicrobial activity evaluation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9414590/
https://www.ncbi.nlm.nih.gov/pubmed/36014322
http://dx.doi.org/10.3390/molecules27165082
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