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Novel 2-Acetamido-2-ylidene-4-imidazole Derivatives (El-Saghier Reaction): Green Synthesis, Biological Assessment, and Molecular Docking
[Image: see text] El-Saghier reaction is the novel, general, and green reaction of various amines with ethyl cyanoacetate and ethyl glycinate hydrochloride. A new series of imidazolidin-4-ones and bis-N-(alkyl/aryl) imidazolidin-4-ones was synthesized in a sequential, one-pot procedure under neat co...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10448697/ https://www.ncbi.nlm.nih.gov/pubmed/37636903 http://dx.doi.org/10.1021/acsomega.3c03767 |
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author | El-Saghier, Ahmed M. Abdou, Aly Mohamed, Mounir A. A. Abd El-Lateef, Hany M. Kadry, Asmaa M. |
author_facet | El-Saghier, Ahmed M. Abdou, Aly Mohamed, Mounir A. A. Abd El-Lateef, Hany M. Kadry, Asmaa M. |
author_sort | El-Saghier, Ahmed M. |
collection | PubMed |
description | [Image: see text] El-Saghier reaction is the novel, general, and green reaction of various amines with ethyl cyanoacetate and ethyl glycinate hydrochloride. A new series of imidazolidin-4-ones and bis-N-(alkyl/aryl) imidazolidin-4-ones was synthesized in a sequential, one-pot procedure under neat conditions for 2 h at 70 °C. Excellent high yields (90–98%) were achieved in a short period of time while avoiding issues related to the hazardous solvents utilized (cost, safety, and pollution). The spectrum analyses and elemental data of the newly synthesized compounds helped us to clarify their structures. The obtained compounds were tested for antibacterial activity in vitro and compared to the standard antibiotic chloramphenicol as the standard, measuring the inhibition zone (nm) and activity index (%). With an antibacterial percentage value of 80.0 against Escherichia coli, N,N′-(propane-1,3-diyl) bis(2-(4-oxo-4,5-dihydro-1H-imidazole-2-yl) acetamide) proved to be the most effective. Antimicrobial activity was confirmed by a molecular docking investigation to investigate how chemicals bind to the bacterial FabH–CoA complex in E. coli (PDB ID: 1HNJ). |
format | Online Article Text |
id | pubmed-10448697 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-104486972023-08-25 Novel 2-Acetamido-2-ylidene-4-imidazole Derivatives (El-Saghier Reaction): Green Synthesis, Biological Assessment, and Molecular Docking El-Saghier, Ahmed M. Abdou, Aly Mohamed, Mounir A. A. Abd El-Lateef, Hany M. Kadry, Asmaa M. ACS Omega [Image: see text] El-Saghier reaction is the novel, general, and green reaction of various amines with ethyl cyanoacetate and ethyl glycinate hydrochloride. A new series of imidazolidin-4-ones and bis-N-(alkyl/aryl) imidazolidin-4-ones was synthesized in a sequential, one-pot procedure under neat conditions for 2 h at 70 °C. Excellent high yields (90–98%) were achieved in a short period of time while avoiding issues related to the hazardous solvents utilized (cost, safety, and pollution). The spectrum analyses and elemental data of the newly synthesized compounds helped us to clarify their structures. The obtained compounds were tested for antibacterial activity in vitro and compared to the standard antibiotic chloramphenicol as the standard, measuring the inhibition zone (nm) and activity index (%). With an antibacterial percentage value of 80.0 against Escherichia coli, N,N′-(propane-1,3-diyl) bis(2-(4-oxo-4,5-dihydro-1H-imidazole-2-yl) acetamide) proved to be the most effective. Antimicrobial activity was confirmed by a molecular docking investigation to investigate how chemicals bind to the bacterial FabH–CoA complex in E. coli (PDB ID: 1HNJ). American Chemical Society 2023-08-09 /pmc/articles/PMC10448697/ /pubmed/37636903 http://dx.doi.org/10.1021/acsomega.3c03767 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 | El-Saghier, Ahmed M. Abdou, Aly Mohamed, Mounir A. A. Abd El-Lateef, Hany M. Kadry, Asmaa M. Novel 2-Acetamido-2-ylidene-4-imidazole Derivatives (El-Saghier Reaction): Green Synthesis, Biological Assessment, and Molecular Docking |
title | Novel 2-Acetamido-2-ylidene-4-imidazole
Derivatives
(El-Saghier Reaction): Green Synthesis, Biological Assessment, and
Molecular Docking |
title_full | Novel 2-Acetamido-2-ylidene-4-imidazole
Derivatives
(El-Saghier Reaction): Green Synthesis, Biological Assessment, and
Molecular Docking |
title_fullStr | Novel 2-Acetamido-2-ylidene-4-imidazole
Derivatives
(El-Saghier Reaction): Green Synthesis, Biological Assessment, and
Molecular Docking |
title_full_unstemmed | Novel 2-Acetamido-2-ylidene-4-imidazole
Derivatives
(El-Saghier Reaction): Green Synthesis, Biological Assessment, and
Molecular Docking |
title_short | Novel 2-Acetamido-2-ylidene-4-imidazole
Derivatives
(El-Saghier Reaction): Green Synthesis, Biological Assessment, and
Molecular Docking |
title_sort | novel 2-acetamido-2-ylidene-4-imidazole
derivatives
(el-saghier reaction): green synthesis, biological assessment, and
molecular docking |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10448697/ https://www.ncbi.nlm.nih.gov/pubmed/37636903 http://dx.doi.org/10.1021/acsomega.3c03767 |
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