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Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives
The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8399259/ https://www.ncbi.nlm.nih.gov/pubmed/34443693 http://dx.doi.org/10.3390/molecules26165107 |
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author | Apostol, Theodora-Venera Chifiriuc, Mariana Carmen Draghici, Constantin Socea, Laura-Ileana Marutescu, Luminita Gabriela Olaru, Octavian Tudorel Nitulescu, George Mihai Pahontu, Elena Mihaela Saramet, Gabriel Barbuceanu, Stefania-Felicia |
author_facet | Apostol, Theodora-Venera Chifiriuc, Mariana Carmen Draghici, Constantin Socea, Laura-Ileana Marutescu, Luminita Gabriela Olaru, Octavian Tudorel Nitulescu, George Mihai Pahontu, Elena Mihaela Saramet, Gabriel Barbuceanu, Stefania-Felicia |
author_sort | Apostol, Theodora-Venera |
collection | PubMed |
description | The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, (1)H- and (13)C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia magna. Also, in silico studies regarding their potential mechanism of action and toxicity were performed. The antimicrobial evaluation revealed that the 2-{4-[(4-chlorophenyl)sulfonyl]benzamido}-3-methylbutanoic acid and the corresponding 1,3-oxazol-5(4H)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the C. albicans strain. |
format | Online Article Text |
id | pubmed-8399259 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-83992592021-08-29 Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives Apostol, Theodora-Venera Chifiriuc, Mariana Carmen Draghici, Constantin Socea, Laura-Ileana Marutescu, Luminita Gabriela Olaru, Octavian Tudorel Nitulescu, George Mihai Pahontu, Elena Mihaela Saramet, Gabriel Barbuceanu, Stefania-Felicia Molecules Article The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, (1)H- and (13)C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia magna. Also, in silico studies regarding their potential mechanism of action and toxicity were performed. The antimicrobial evaluation revealed that the 2-{4-[(4-chlorophenyl)sulfonyl]benzamido}-3-methylbutanoic acid and the corresponding 1,3-oxazol-5(4H)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the C. albicans strain. MDPI 2021-08-23 /pmc/articles/PMC8399259/ /pubmed/34443693 http://dx.doi.org/10.3390/molecules26165107 Text en © 2021 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 Apostol, Theodora-Venera Chifiriuc, Mariana Carmen Draghici, Constantin Socea, Laura-Ileana Marutescu, Luminita Gabriela Olaru, Octavian Tudorel Nitulescu, George Mihai Pahontu, Elena Mihaela Saramet, Gabriel Barbuceanu, Stefania-Felicia Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives |
title | Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives |
title_full | Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives |
title_fullStr | Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives |
title_full_unstemmed | Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives |
title_short | Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives |
title_sort | synthesis, in silico and in vitro evaluation of antimicrobial and toxicity features of new 4-[(4-chlorophenyl)sulfonyl]benzoic acid derivatives |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8399259/ https://www.ncbi.nlm.nih.gov/pubmed/34443693 http://dx.doi.org/10.3390/molecules26165107 |
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