C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications

Abstract A Novel (E)-2-(1-(3-aminophenyl)ethylidene)hydrazinecarboxamide 1 was synthesized by traditional method and converted to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide 2 by single step in DMSO at room temperature. Synthesized compound 1 was analysed by spectroscopy (NMR and LC–MS) technique...

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Autores principales:	M. Sennappan, Sinosh Skariyachan, Praveen B. Managutti, Shubha Shridhar Gunaga
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2020
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/0ca784cfcbd44f6db0ad51182aab511d
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spelling	oai:doaj.org-article:0ca784cfcbd44f6db0ad51182aab511d2021-12-02T13:58:10ZC-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications10.1038/s41598-020-79027-12045-2322https://doaj.org/article/0ca784cfcbd44f6db0ad51182aab511d2020-12-01T00:00:00Zhttps://doi.org/10.1038/s41598-020-79027-1https://doaj.org/toc/2045-2322Abstract A Novel (E)-2-(1-(3-aminophenyl)ethylidene)hydrazinecarboxamide 1 was synthesized by traditional method and converted to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide 2 by single step in DMSO at room temperature. Synthesized compound 1 was analysed by spectroscopy (NMR and LC–MS) techniques and molecule 2 was characterized using single crystal X-ray diffraction and spectroscopy (NMR and GC–MS) techniques. These analytical technique results revealed that, C-demethylation and 1, 2 amino shift in phenyl ring of compound 1 gives molecule 2. DNA binding studies of compounds 1 and 2 was carried out by electronic absorption spectroscopy. This result revealed that, compounds 1 and 2 showed hyperchromism with bathochromic shift. Anticancer activity of compounds 1 and 2 is carried out by molecular docking with five receptors.Computer aided virtual screening demonstrated that the synthesized molecules possess ideal drug likeliness, pharmacokinetics features, toxicity profile for structure based drug discovery. The molecular docking studies revealed that the synthesized molecules are significant binding with the five selected cancer receptors with minimum binding energy (kcal/mol), number of hydrogen bonds, weak interaction, docking score and cluster RMS. The docking studies also suggested that the molecules showed interactions with DNA and the theoretical values of the binding are comparable with that of the experimental values. Hirshfeld surface analysis was used to analyze and quantify the intermolecular interactions in the crystal structure of compound 2.M. SennappanSinosh SkariyachanPraveen B. ManaguttiShubha Shridhar GunagaNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 10, Iss 1, Pp 1-17 (2020)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q M. Sennappan Sinosh Skariyachan Praveen B. Managutti Shubha Shridhar Gunaga C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications
description	Abstract A Novel (E)-2-(1-(3-aminophenyl)ethylidene)hydrazinecarboxamide 1 was synthesized by traditional method and converted to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide 2 by single step in DMSO at room temperature. Synthesized compound 1 was analysed by spectroscopy (NMR and LC–MS) techniques and molecule 2 was characterized using single crystal X-ray diffraction and spectroscopy (NMR and GC–MS) techniques. These analytical technique results revealed that, C-demethylation and 1, 2 amino shift in phenyl ring of compound 1 gives molecule 2. DNA binding studies of compounds 1 and 2 was carried out by electronic absorption spectroscopy. This result revealed that, compounds 1 and 2 showed hyperchromism with bathochromic shift. Anticancer activity of compounds 1 and 2 is carried out by molecular docking with five receptors.Computer aided virtual screening demonstrated that the synthesized molecules possess ideal drug likeliness, pharmacokinetics features, toxicity profile for structure based drug discovery. The molecular docking studies revealed that the synthesized molecules are significant binding with the five selected cancer receptors with minimum binding energy (kcal/mol), number of hydrogen bonds, weak interaction, docking score and cluster RMS. The docking studies also suggested that the molecules showed interactions with DNA and the theoretical values of the binding are comparable with that of the experimental values. Hirshfeld surface analysis was used to analyze and quantify the intermolecular interactions in the crystal structure of compound 2.
format	article
author	M. Sennappan Sinosh Skariyachan Praveen B. Managutti Shubha Shridhar Gunaga
author_facet	M. Sennappan Sinosh Skariyachan Praveen B. Managutti Shubha Shridhar Gunaga
author_sort	M. Sennappan
title	C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications
title_short	C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications
title_full	C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications
title_fullStr	C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications
title_full_unstemmed	C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications
title_sort	c-demethylation and 1, 2-amino shift in (e)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (e)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications
publisher	Nature Portfolio
publishDate	2020
url	https://doaj.org/article/0ca784cfcbd44f6db0ad51182aab511d
work_keys_str_mv	AT msennappan cdemethylationand12aminoshiftine213aminophenylethylidenehydrazinecarboxamidetoe22aminobenzylidenehydrazinecarboxamideandtheirapplications AT sinoshskariyachan cdemethylationand12aminoshiftine213aminophenylethylidenehydrazinecarboxamidetoe22aminobenzylidenehydrazinecarboxamideandtheirapplications AT praveenbmanagutti cdemethylationand12aminoshiftine213aminophenylethylidenehydrazinecarboxamidetoe22aminobenzylidenehydrazinecarboxamideandtheirapplications AT shubhashridhargunaga cdemethylationand12aminoshiftine213aminophenylethylidenehydrazinecarboxamidetoe22aminobenzylidenehydrazinecarboxamideandtheirapplications
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C-demethylation and 1, 2-amino shift in (E)-2-(1-(3-aminophenyl) ethylidene)hydrazinecarboxamide to (E)-2-(2-aminobenzylidene)hydrazinecarboxamide and their applications

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