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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...

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Autores principales: Singh, Nasseb, Abrol, Vidushi, Parihar, Sarita, Kumar, Satish, Khanum, Ghazala, Mir, Jan Mohammad, Dar, Alamgir Ahmad, Jaglan, Sundeep, Sillanpää, Mika, Al-Farraj, Saleh
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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.
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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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