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Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative

The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activit...

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Detalles Bibliográficos
Autores principales: Tayade, Kundan, Yeom, Gyu-Seong, Sahoo, Suban K., Puschmann, Horst, Nimse, Satish Balasaheb, Kuwar, Anil
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9686989/
https://www.ncbi.nlm.nih.gov/pubmed/36358512
http://dx.doi.org/10.3390/antiox11112138
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author Tayade, Kundan
Yeom, Gyu-Seong
Sahoo, Suban K.
Puschmann, Horst
Nimse, Satish Balasaheb
Kuwar, Anil
author_facet Tayade, Kundan
Yeom, Gyu-Seong
Sahoo, Suban K.
Puschmann, Horst
Nimse, Satish Balasaheb
Kuwar, Anil
author_sort Tayade, Kundan
collection PubMed
description The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activity of the Schiff base 4,4′-((1E,1′E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (compound 2). We have also isolated the side product compound 1 and characterized it using single X-ray crystallography. The crystal structure of compound 1 depicts that the ensuing C–H···N hydrogen bonding interaction is presented and discussed herein. In addition, the calculations using density functional theory (DFT) approximation supported by experimental (1)H and (13)C NMR studies on the key compound 2 are reported. The results of theoretical and experimental (1)H and (13)C NMR were concordant. The antioxidant activity of compound 2 was determined by using 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS(•+)) radical cation assays and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Compound 2 demonstrated excellent antioxidant activity in ABTS assay (IC(50) = 4.30 ± 0.21 µM) and DPPH assay (IC(50) = 81.06 ± 0.72 µM) with almost no cytotoxicity below 25 µM.
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spelling pubmed-96869892022-11-25 Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative Tayade, Kundan Yeom, Gyu-Seong Sahoo, Suban K. Puschmann, Horst Nimse, Satish Balasaheb Kuwar, Anil Antioxidants (Basel) Article The hydrazine derivatives are known to possess several biological activities including anticancer, antibacterial and anti-fungal, anticonvulsant, and antioxidant. This communication presents the synthesis, X-ray crystal structure analysis, DFT calculations, cell cytotoxicity, and antioxidant activity of the Schiff base 4,4′-((1E,1′E)-hydrazine-1,2-diylidenebis(ethan-1-yl-1-ylidene))bis(benzene-1,3-diol) (compound 2). We have also isolated the side product compound 1 and characterized it using single X-ray crystallography. The crystal structure of compound 1 depicts that the ensuing C–H···N hydrogen bonding interaction is presented and discussed herein. In addition, the calculations using density functional theory (DFT) approximation supported by experimental (1)H and (13)C NMR studies on the key compound 2 are reported. The results of theoretical and experimental (1)H and (13)C NMR were concordant. The antioxidant activity of compound 2 was determined by using 2,2′-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS(•+)) radical cation assays and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical assay. Compound 2 demonstrated excellent antioxidant activity in ABTS assay (IC(50) = 4.30 ± 0.21 µM) and DPPH assay (IC(50) = 81.06 ± 0.72 µM) with almost no cytotoxicity below 25 µM. MDPI 2022-10-28 /pmc/articles/PMC9686989/ /pubmed/36358512 http://dx.doi.org/10.3390/antiox11112138 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tayade, Kundan
Yeom, Gyu-Seong
Sahoo, Suban K.
Puschmann, Horst
Nimse, Satish Balasaheb
Kuwar, Anil
Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative
title Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative
title_full Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative
title_fullStr Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative
title_full_unstemmed Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative
title_short Exploration of Molecular Structure, DFT Calculations, and Antioxidant Activity of a Hydrazone Derivative
title_sort exploration of molecular structure, dft calculations, and antioxidant activity of a hydrazone derivative
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9686989/
https://www.ncbi.nlm.nih.gov/pubmed/36358512
http://dx.doi.org/10.3390/antiox11112138
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