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Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents

N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides (5a–h) and N-[2-(2-{[2-(acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides (5i–l) were synthesized and characterized with different analytical tools. N-Acetylisatines 4a–d were subjected to ring ope...

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Autores principales: Almutairi, Maha S., Zakaria, Azza S., Al-Wabli, Reem I., Joe, I. Hubert, Abdelhameed, Ali S., Attia, Mohamed I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6102541/
https://www.ncbi.nlm.nih.gov/pubmed/29710842
http://dx.doi.org/10.3390/molecules23051043
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author Almutairi, Maha S.
Zakaria, Azza S.
Al-Wabli, Reem I.
Joe, I. Hubert
Abdelhameed, Ali S.
Attia, Mohamed I.
author_facet Almutairi, Maha S.
Zakaria, Azza S.
Al-Wabli, Reem I.
Joe, I. Hubert
Abdelhameed, Ali S.
Attia, Mohamed I.
author_sort Almutairi, Maha S.
collection PubMed
description N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides (5a–h) and N-[2-(2-{[2-(acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides (5i–l) were synthesized and characterized with different analytical tools. N-Acetylisatines 4a–d were subjected to ring opening at their C2 carbons with the aid of different indole-bearing hydrazides 3a,b and 7 to afford the respective glyoxylamides 5a–l. The antimicrobial activity of the target compounds 5a–l was assessed with the aid of Diameter of the Inhibition Zone (DIZ) and Minimum Inhibitory Concentration (MIC) assays against a panel of Gram-positive and Gram-negative bacteria and certain fungal strains. The antimicrobial screening revealed that Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans are the most sensitive microorganisms towards the synthesized compounds 5a–l. In addition, compounds 5c and 5h emerged as the most active congeners towards Staphylococcus aureus and Candida albicans, respectively. Molecular docking studies revealed the possible binding mode of compounds 5c and 5h to their target proteins.
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spelling pubmed-61025412018-11-13 Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents Almutairi, Maha S. Zakaria, Azza S. Al-Wabli, Reem I. Joe, I. Hubert Abdelhameed, Ali S. Attia, Mohamed I. Molecules Article N-(2-{[2-(1H-Indol-2-ylcarbonyl)hydrazinyl](oxo)acetyl}phenyl)acetamides (5a–h) and N-[2-(2-{[2-(acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides (5i–l) were synthesized and characterized with different analytical tools. N-Acetylisatines 4a–d were subjected to ring opening at their C2 carbons with the aid of different indole-bearing hydrazides 3a,b and 7 to afford the respective glyoxylamides 5a–l. The antimicrobial activity of the target compounds 5a–l was assessed with the aid of Diameter of the Inhibition Zone (DIZ) and Minimum Inhibitory Concentration (MIC) assays against a panel of Gram-positive and Gram-negative bacteria and certain fungal strains. The antimicrobial screening revealed that Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, and Candida albicans are the most sensitive microorganisms towards the synthesized compounds 5a–l. In addition, compounds 5c and 5h emerged as the most active congeners towards Staphylococcus aureus and Candida albicans, respectively. Molecular docking studies revealed the possible binding mode of compounds 5c and 5h to their target proteins. MDPI 2018-04-29 /pmc/articles/PMC6102541/ /pubmed/29710842 http://dx.doi.org/10.3390/molecules23051043 Text en © 2018 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Almutairi, Maha S.
Zakaria, Azza S.
Al-Wabli, Reem I.
Joe, I. Hubert
Abdelhameed, Ali S.
Attia, Mohamed I.
Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents
title Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents
title_full Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents
title_fullStr Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents
title_full_unstemmed Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents
title_short Synthesis, Spectroscopic Identification and Molecular Docking of Certain N-(2-{[2-(1H-Indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and N-[2-(2-{[2-(Acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1H-indole-2-carboxamides: New Antimicrobial Agents
title_sort synthesis, spectroscopic identification and molecular docking of certain n-(2-{[2-(1h-indol-2-ylcarbonyl) hydrazinyl](oxo)acetyl}phenyl)acetamides and n-[2-(2-{[2-(acetylamino)phenyl](oxo)acetyl}hydrazinyl)-2-oxoethyl]-1h-indole-2-carboxamides: new antimicrobial agents
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6102541/
https://www.ncbi.nlm.nih.gov/pubmed/29710842
http://dx.doi.org/10.3390/molecules23051043
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