LAPSE:2023.1817
Published Article
LAPSE:2023.1817
Synthesis, Characterization, and Biological Evaluation of Novel N-{4-[(4-Bromophenyl)sulfonyl]benzoyl}-L-valine Derivatives
February 21, 2023
Abstract
In this article, we present the design and synthesis of novel compounds, containing in their molecules an L-valine residue and a 4-[(4-bromophenyl)sulfonyl]phenyl moiety, which belong to N-acyl-α-amino acids, 4H-1,3-oxazol-5-ones, 2-acylamino ketones, and 1,3-oxazoles chemotypes. The synthesized compounds were characterized through elemental analysis, MS, NMR, UV/VIS, and FTIR spectroscopic techniques, the data obtained being in accordance with the assigned structures. Their purities were verified by reversed-phase HPLC. The new compounds were tested for antimicrobial action against bacterial and fungal strains, for antioxidant activity by DPPH, ABTS, and ferric reducing power assays, and for toxicity on freshwater cladoceran Daphnia magna Straus. Furthermore, in silico studies were performed concerning the potential antimicrobial effect and toxicity. The results of antimicrobial activity, antioxidant effect, and toxicity assays, as well as of in silico analysis revealed a promising potential of N-{4-[(4-bromophenyl)sulfonyl]benzoyl}-L-valine and 2-{4-[(4-bromophenyl)sulfonyl]phenyl}-4-isopropyl-4H-1,3-oxazol-5-one for developing novel antimicrobial agents to fight Gram-positive pathogens, and particularly Enterococcus faecium biofilm-associated infections.
In this article, we present the design and synthesis of novel compounds, containing in their molecules an L-valine residue and a 4-[(4-bromophenyl)sulfonyl]phenyl moiety, which belong to N-acyl-α-amino acids, 4H-1,3-oxazol-5-ones, 2-acylamino ketones, and 1,3-oxazoles chemotypes. The synthesized compounds were characterized through elemental analysis, MS, NMR, UV/VIS, and FTIR spectroscopic techniques, the data obtained being in accordance with the assigned structures. Their purities were verified by reversed-phase HPLC. The new compounds were tested for antimicrobial action against bacterial and fungal strains, for antioxidant activity by DPPH, ABTS, and ferric reducing power assays, and for toxicity on freshwater cladoceran Daphnia magna Straus. Furthermore, in silico studies were performed concerning the potential antimicrobial effect and toxicity. The results of antimicrobial activity, antioxidant effect, and toxicity assays, as well as of in silico analysis revealed a promising potential of N-{4-[(4-bromophenyl)sulfonyl]benzoyl}-L-valine and 2-{4-[(4-bromophenyl)sulfonyl]phenyl}-4-isopropyl-4H-1,3-oxazol-5-one for developing novel antimicrobial agents to fight Gram-positive pathogens, and particularly Enterococcus faecium biofilm-associated infections.
Record ID
Keywords
1,3-oxazole, 2-acylamino ketone, 4H-1,3-oxazol-5-one, alternative toxicity testing, antimicrobial and antibiofilm actions, antioxidant effect, diphenyl sulfone scaffold, drug design, in silico studies, N-acyl-L-valine
Suggested Citation
Apostol TV, Chifiriuc MC, Socea LI, Draghici C, Olaru OT, Nitulescu GM, Visan DC, Marutescu LG, Pahontu EM, Saramet G, Barbuceanu SF. Synthesis, Characterization, and Biological Evaluation of Novel N-{4-[(4-Bromophenyl)sulfonyl]benzoyl}-L-valine Derivatives. (2023). LAPSE:2023.1817
Author Affiliations
Apostol TV: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania [ORCID]
Chifiriuc MC: Department of Botany and Microbiology, Faculty of Biology, University of Bucharest, 1-3 Intrarea Portocalelor, District 6, 60101 Bucharest, Romania [ORCID]
Socea LI: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania [ORCID]
Draghici C: “Costin D. Nenițescu” Centre of Organic Chemistry, Romanian Academy, 202 B Splaiul Independenței, District 6, 060023 Bucharest, Romania
Olaru OT: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Nitulescu GM: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania [ORCID]
Visan DC: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania [ORCID]
Marutescu LG: Department of Botany and Microbiology, Faculty of Biology, University of Bucharest, 1-3 Intrarea Portocalelor, District 6, 60101 Bucharest, Romania
Pahontu EM: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Saramet G: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Barbuceanu SF: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Chifiriuc MC: Department of Botany and Microbiology, Faculty of Biology, University of Bucharest, 1-3 Intrarea Portocalelor, District 6, 60101 Bucharest, Romania [ORCID]
Socea LI: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania [ORCID]
Draghici C: “Costin D. Nenițescu” Centre of Organic Chemistry, Romanian Academy, 202 B Splaiul Independenței, District 6, 060023 Bucharest, Romania
Olaru OT: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Nitulescu GM: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania [ORCID]
Visan DC: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania [ORCID]
Marutescu LG: Department of Botany and Microbiology, Faculty of Biology, University of Bucharest, 1-3 Intrarea Portocalelor, District 6, 60101 Bucharest, Romania
Pahontu EM: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Saramet G: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Barbuceanu SF: Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia Street, District 2, 020956 Bucharest, Romania
Journal Name
Processes
Volume
10
Issue
9
First Page
1800
Year
2022
Publication Date
2022-09-07
ISSN
2227-9717
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Original Submission
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PII: pr10091800, Publication Type: Journal Article
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LAPSE:2023.1817
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https://doi.org/10.3390/pr10091800
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