Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: El-Saghier, Ahmed M., Abdou, Aly, Mohamed, Mounir A. A., Abd El-Lateef, Hany M., Kadry, Asmaa M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
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
_version_ 1785094792610316288
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
work_keys_str_mv AT elsaghierahmedm novel2acetamido2ylidene4imidazolederivativeselsaghierreactiongreensynthesisbiologicalassessmentandmoleculardocking
AT abdoualy novel2acetamido2ylidene4imidazolederivativeselsaghierreactiongreensynthesisbiologicalassessmentandmoleculardocking
AT mohamedmouniraa novel2acetamido2ylidene4imidazolederivativeselsaghierreactiongreensynthesisbiologicalassessmentandmoleculardocking
AT abdellateefhanym novel2acetamido2ylidene4imidazolederivativeselsaghierreactiongreensynthesisbiologicalassessmentandmoleculardocking
AT kadryasmaam novel2acetamido2ylidene4imidazolederivativeselsaghierreactiongreensynthesisbiologicalassessmentandmoleculardocking