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Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines
[Image: see text] In the present study, a series of benzotriazole-based β-amino alcohols were efficiently synthesized in excellent yields via aminolysis of benzotriazolated epoxides under catalyst- and solvent-free conditions. Further these β-amino alcohols were successfully utilized to synthesize t...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10634288/ https://www.ncbi.nlm.nih.gov/pubmed/37969976 http://dx.doi.org/10.1021/acsomega.3c07315 |
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author | Singh, Nasseb Abrol, Vidushi Parihar, Sarita Kumar, Satish Khanum, Ghazala Mir, Jan Mohammad Dar, Alamgir Ahmad Jaglan, Sundeep Sillanpää, Mika Al-Farraj, Saleh |
author_facet | Singh, Nasseb Abrol, Vidushi Parihar, Sarita Kumar, Satish Khanum, Ghazala Mir, Jan Mohammad Dar, Alamgir Ahmad Jaglan, Sundeep Sillanpää, Mika Al-Farraj, Saleh |
author_sort | Singh, Nasseb |
collection | PubMed |
description | [Image: see text] In the present study, a series of benzotriazole-based β-amino alcohols were efficiently synthesized in excellent yields via aminolysis of benzotriazolated epoxides under catalyst- and solvent-free conditions. Further these β-amino alcohols were successfully utilized to synthesize the corresponding benzotriazole-based oxazolidine heterocyclic derivatives. All the synthesized compounds were characterized by various spectroscopic techniques such as (1)H NMR, (13)C NMR, and mass spectroscopy for structure elucidation. The compounds were subjected to a microtiter plate-based antimicrobial assay. The antimicrobial activity results reveal that the compounds 4a, 4e, and 5f were found to be active against Staphylococcus aureus (ATCC-25923) with minimum inhibitory concentrations (MICs) of 32, 8, and 64 μM, respectively. Also, the compounds 4a, 4e, 4k, 4i, 4m, 4n, 4o, 5d, 5e, 5f, 5g, and 5h showed effective activity against Bacillus subtilis (ATCC 6633) with MICs of 64, 16, 16, 16, 64, 16, 64, 64, 32, 64, 8, and 16 μM, respectively. A biological investigation was conducted, including molecular docking of two compounds with several receptors to identify and confirm the best ligand–protein interactions. Hence, this study found a significant strategy to diversify the chemical molecules. The synthesized compounds play a potential role as an antibacterial intensifier against some pathogenic bacteria for the development of antibacterial substances. |
format | Online Article Text |
id | pubmed-10634288 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-106342882023-11-15 Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines Singh, Nasseb Abrol, Vidushi Parihar, Sarita Kumar, Satish Khanum, Ghazala Mir, Jan Mohammad Dar, Alamgir Ahmad Jaglan, Sundeep Sillanpää, Mika Al-Farraj, Saleh ACS Omega [Image: see text] In the present study, a series of benzotriazole-based β-amino alcohols were efficiently synthesized in excellent yields via aminolysis of benzotriazolated epoxides under catalyst- and solvent-free conditions. Further these β-amino alcohols were successfully utilized to synthesize the corresponding benzotriazole-based oxazolidine heterocyclic derivatives. All the synthesized compounds were characterized by various spectroscopic techniques such as (1)H NMR, (13)C NMR, and mass spectroscopy for structure elucidation. The compounds were subjected to a microtiter plate-based antimicrobial assay. The antimicrobial activity results reveal that the compounds 4a, 4e, and 5f were found to be active against Staphylococcus aureus (ATCC-25923) with minimum inhibitory concentrations (MICs) of 32, 8, and 64 μM, respectively. Also, the compounds 4a, 4e, 4k, 4i, 4m, 4n, 4o, 5d, 5e, 5f, 5g, and 5h showed effective activity against Bacillus subtilis (ATCC 6633) with MICs of 64, 16, 16, 16, 64, 16, 64, 64, 32, 64, 8, and 16 μM, respectively. A biological investigation was conducted, including molecular docking of two compounds with several receptors to identify and confirm the best ligand–protein interactions. Hence, this study found a significant strategy to diversify the chemical molecules. The synthesized compounds play a potential role as an antibacterial intensifier against some pathogenic bacteria for the development of antibacterial substances. American Chemical Society 2023-10-27 /pmc/articles/PMC10634288/ /pubmed/37969976 http://dx.doi.org/10.1021/acsomega.3c07315 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Singh, Nasseb Abrol, Vidushi Parihar, Sarita Kumar, Satish Khanum, Ghazala Mir, Jan Mohammad Dar, Alamgir Ahmad Jaglan, Sundeep Sillanpää, Mika Al-Farraj, Saleh Design, Synthesis, Molecular Docking, and In Vitro Antibacterial Evaluation of Benzotriazole-Based β-Amino Alcohols and Their Corresponding 1,3-Oxazolidines |
title | Design, Synthesis, Molecular Docking, and In Vitro
Antibacterial Evaluation of Benzotriazole-Based β-Amino
Alcohols and Their Corresponding 1,3-Oxazolidines |
title_full | Design, Synthesis, Molecular Docking, and In Vitro
Antibacterial Evaluation of Benzotriazole-Based β-Amino
Alcohols and Their Corresponding 1,3-Oxazolidines |
title_fullStr | Design, Synthesis, Molecular Docking, and In Vitro
Antibacterial Evaluation of Benzotriazole-Based β-Amino
Alcohols and Their Corresponding 1,3-Oxazolidines |
title_full_unstemmed | Design, Synthesis, Molecular Docking, and In Vitro
Antibacterial Evaluation of Benzotriazole-Based β-Amino
Alcohols and Their Corresponding 1,3-Oxazolidines |
title_short | Design, Synthesis, Molecular Docking, and In Vitro
Antibacterial Evaluation of Benzotriazole-Based β-Amino
Alcohols and Their Corresponding 1,3-Oxazolidines |
title_sort | design, synthesis, molecular docking, and in vitro
antibacterial evaluation of benzotriazole-based β-amino
alcohols and their corresponding 1,3-oxazolidines |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10634288/ https://www.ncbi.nlm.nih.gov/pubmed/37969976 http://dx.doi.org/10.1021/acsomega.3c07315 |
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