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., <i>N</i>-acyl-α-amino acids, 1,3-oxazol-5(4<i>H</i>)-ones, <i>N</i>-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-ch...
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| Format: | Article |
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MDPI AG
2021-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/16/5107 |
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| author | Theodora-Venera Apostol Mariana Carmen Chifiriuc Constantin Draghici Laura-Ileana Socea Luminita Gabriela Marutescu Octavian Tudorel Olaru George Mihai Nitulescu Elena Mihaela Pahontu Gabriel Saramet Stefania-Felicia Barbuceanu |
| author_facet | Theodora-Venera Apostol Mariana Carmen Chifiriuc Constantin Draghici Laura-Ileana Socea Luminita Gabriela Marutescu Octavian Tudorel Olaru George Mihai Nitulescu Elena Mihaela Pahontu Gabriel Saramet Stefania-Felicia Barbuceanu |
| author_sort | Theodora-Venera Apostol |
| collection | DOAJ |
| description | The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., <i>N</i>-acyl-α-amino acids, 1,3-oxazol-5(4<i>H</i>)-ones, <i>N</i>-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, <sup>1</sup>H- and <sup>13</sup>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 <i>Daphnia magna</i>. 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(4<i>H</i>)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the <i>C. albicans</i> strain. |
| first_indexed | 2024-03-10T08:32:00Z |
| format | Article |
| id | doaj.art-368255841169486093799b60b9c1c2bb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T08:32:00Z |
| publishDate | 2021-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-368255841169486093799b60b9c1c2bb2023-11-22T08:56:44ZengMDPI AGMolecules1420-30492021-08-012616510710.3390/molecules26165107Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid DerivativesTheodora-Venera Apostol0Mariana Carmen Chifiriuc1Constantin Draghici2Laura-Ileana Socea3Luminita Gabriela Marutescu4Octavian Tudorel Olaru5George Mihai Nitulescu6Elena Mihaela Pahontu7Gabriel Saramet8Stefania-Felicia Barbuceanu9Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, 020956 Bucharest, RomaniaDepartment of Botany and Microbiology, Faculty of Biology, University of Bucharest, 1-3 Aleea Portocalelor, 60101 Bucharest, Romania“Costin D. Nenițescu” Centre of Organic Chemistry, Romanian Academy, 202 B Splaiul Independenței, 060023 Bucharest, RomaniaFaculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, 020956 Bucharest, RomaniaDepartment of Botany and Microbiology, Faculty of Biology, University of Bucharest, 1-3 Aleea Portocalelor, 60101 Bucharest, RomaniaFaculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, 020956 Bucharest, RomaniaFaculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, 020956 Bucharest, RomaniaFaculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, 020956 Bucharest, RomaniaFaculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, 020956 Bucharest, RomaniaFaculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, 020956 Bucharest, RomaniaThe multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., <i>N</i>-acyl-α-amino acids, 1,3-oxazol-5(4<i>H</i>)-ones, <i>N</i>-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, <sup>1</sup>H- and <sup>13</sup>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 <i>Daphnia magna</i>. 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(4<i>H</i>)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the <i>C. albicans</i> strain.https://www.mdpi.com/1420-3049/26/16/5107<i>N</i>-acyl-α-amino acid4-isopropyl-1,3-oxazol-5(4<i>H</i>)-one<i>N</i>-acyl-α-amino ketone4-isopropyl-1,3-oxazoleantimicrobial activityantibiofilm agents |
| spellingShingle | Theodora-Venera Apostol Mariana Carmen Chifiriuc Constantin Draghici Laura-Ileana Socea Luminita Gabriela Marutescu Octavian Tudorel Olaru George Mihai Nitulescu Elena Mihaela Pahontu Gabriel Saramet Stefania-Felicia Barbuceanu Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives Molecules <i>N</i>-acyl-α-amino acid 4-isopropyl-1,3-oxazol-5(4<i>H</i>)-one <i>N</i>-acyl-α-amino ketone 4-isopropyl-1,3-oxazole antimicrobial activity antibiofilm agents |
| 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 | <i>N</i>-acyl-α-amino acid 4-isopropyl-1,3-oxazol-5(4<i>H</i>)-one <i>N</i>-acyl-α-amino ketone 4-isopropyl-1,3-oxazole antimicrobial activity antibiofilm agents |
| url | https://www.mdpi.com/1420-3049/26/16/5107 |
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