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Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents

[Image: see text] The condensation of phthalic anhydride afforded structurally modified isoindoline-1,3-dione derivatives with selected amino-containing compounds. The title compounds (2–30) have been characterized by thin-layer chromatography (TLC), infrared spectroscopy, (1)H and (13)C NMR spectro...

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Autores principales: Ahmad, Iqrar, Pawara, Rahul H., Girase, Rukaiyya T., Pathan, Asama Y., Jagatap, Vilas R., Desai, Nisheeth, Ayipo, Yusuf Oloruntoyin, Surana, Sanjay J., Patel, Harun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9244950/
https://www.ncbi.nlm.nih.gov/pubmed/35785272
http://dx.doi.org/10.1021/acsomega.2c01981
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author Ahmad, Iqrar
Pawara, Rahul H.
Girase, Rukaiyya T.
Pathan, Asama Y.
Jagatap, Vilas R.
Desai, Nisheeth
Ayipo, Yusuf Oloruntoyin
Surana, Sanjay J.
Patel, Harun
author_facet Ahmad, Iqrar
Pawara, Rahul H.
Girase, Rukaiyya T.
Pathan, Asama Y.
Jagatap, Vilas R.
Desai, Nisheeth
Ayipo, Yusuf Oloruntoyin
Surana, Sanjay J.
Patel, Harun
author_sort Ahmad, Iqrar
collection PubMed
description [Image: see text] The condensation of phthalic anhydride afforded structurally modified isoindoline-1,3-dione derivatives with selected amino-containing compounds. The title compounds (2–30) have been characterized by thin-layer chromatography (TLC), infrared spectroscopy, (1)H and (13)C NMR spectroscopy, and mass spectroscopy. All of the compounds were assessed for their antimycobacterial activity toward the H37Rv strain by a dual read-out assay method. Among the synthesized compounds, compound 27 possessed a significant IC(50) of 18 μM, making it the most potent compound of the series. The InhA inhibitory (IC(50)) activity of compound 27 was 8.65 μM in comparison to Triclosan (1.32 μM). Computational studies like density functional theory (DFT) study, molecular docking, and dynamic simulation studies illustrated the reactivity and stability of the synthesized compounds as InhA inhibitors. A quantum-mechanics-based DFT study was carried out to investigate the molecular and electronic properties, reactivities, and nature of bonding present in the synthesized compounds and theoretical vibrational (IR) and isotropic value ((1)H and (13)C NMR) calculations.
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spelling pubmed-92449502022-07-01 Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents Ahmad, Iqrar Pawara, Rahul H. Girase, Rukaiyya T. Pathan, Asama Y. Jagatap, Vilas R. Desai, Nisheeth Ayipo, Yusuf Oloruntoyin Surana, Sanjay J. Patel, Harun ACS Omega [Image: see text] The condensation of phthalic anhydride afforded structurally modified isoindoline-1,3-dione derivatives with selected amino-containing compounds. The title compounds (2–30) have been characterized by thin-layer chromatography (TLC), infrared spectroscopy, (1)H and (13)C NMR spectroscopy, and mass spectroscopy. All of the compounds were assessed for their antimycobacterial activity toward the H37Rv strain by a dual read-out assay method. Among the synthesized compounds, compound 27 possessed a significant IC(50) of 18 μM, making it the most potent compound of the series. The InhA inhibitory (IC(50)) activity of compound 27 was 8.65 μM in comparison to Triclosan (1.32 μM). Computational studies like density functional theory (DFT) study, molecular docking, and dynamic simulation studies illustrated the reactivity and stability of the synthesized compounds as InhA inhibitors. A quantum-mechanics-based DFT study was carried out to investigate the molecular and electronic properties, reactivities, and nature of bonding present in the synthesized compounds and theoretical vibrational (IR) and isotropic value ((1)H and (13)C NMR) calculations. American Chemical Society 2022-06-10 /pmc/articles/PMC9244950/ /pubmed/35785272 http://dx.doi.org/10.1021/acsomega.2c01981 Text en © 2022 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 Ahmad, Iqrar
Pawara, Rahul H.
Girase, Rukaiyya T.
Pathan, Asama Y.
Jagatap, Vilas R.
Desai, Nisheeth
Ayipo, Yusuf Oloruntoyin
Surana, Sanjay J.
Patel, Harun
Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents
title Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents
title_full Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents
title_fullStr Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents
title_full_unstemmed Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents
title_short Synthesis, Molecular Modeling Study, and Quantum-Chemical-Based Investigations of Isoindoline-1,3-diones as Antimycobacterial Agents
title_sort synthesis, molecular modeling study, and quantum-chemical-based investigations of isoindoline-1,3-diones as antimycobacterial agents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9244950/
https://www.ncbi.nlm.nih.gov/pubmed/35785272
http://dx.doi.org/10.1021/acsomega.2c01981
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