Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2023 Aug 9;8(33):30519-30531.
doi: 10.1021/acsomega.3c03767. eCollection 2023 Aug 22.

Novel 2-Acetamido-2-ylidene-4-imidazole Derivatives (El-Saghier Reaction): Green Synthesis, Biological Assessment, and Molecular Docking

Ahmed M El-Saghier  1 , Aly Abdou  1 , Mounir A A Mohamed  1 , Hany M Abd El-Lateef  1   2 , Asmaa M Kadry  1
Affiliations

Novel 2-Acetamido-2-ylidene-4-imidazole Derivatives (El-Saghier Reaction): Green Synthesis, Biological Assessment, and Molecular Docking

Ahmed M El-Saghier et al. ACS Omega. .

Abstract

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).

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Structures of imidazolidin-4-one and imidazole-4-one literature biological activity analogues (A–E).
Scheme 1
Scheme 1. Synthesis of Imidazole-4-one and/or Imidazolidin-4-one Derivatives 4a–m in a Solvent-Free, Sequential One-Pot Method
Scheme 2
Scheme 2. Reaction Mechanism for the Synthesis of N-Cyclohexyl-2-(4-oxo-4,5-dihydro-1H-imidazole-2-yl) Acetamide (4f)
Scheme 3
Scheme 3. Synthesis of bis-N-(Alkyl/Aryl) Acetamido-2-ylidene-4-imidazole Derivatives 6a–d
Figure 2
Figure 2
3D and 2D interaction of docked compounds through the 1HNJ active site.
Figure 2
Figure 2
3D and 2D interaction of docked compounds through the 1HNJ active site.
Figure 2
Figure 2
3D and 2D interaction of docked compounds through the 1HNJ active site.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Albayati M. R.; Kansız S.; Dege N.; Kaya S.; Marzouki R.; Lgaz H.; Salghi R.; Ali I. H.; Alghamdi M. M.; Chung I.-M. Synthesis, crystal structure, Hirshfeld surface analysis and DFT calculations of 2-[(2, 3-dimethylphenyl) amino]-N’-[(E)-thiophen-2-ylmethylidene] benzohydrazide. J. Mol. Struct. 2020, 1205, 127654.10.1016/j.molstruc.2019.127654. - DOI
    1. Mlostoń G.; Celeda M.; Jasiński M.; Urbaniak K.; Boratyński P. J.; Schreiner P. R.; Heimgartner H. 2-Unsubstituted imidazole N-oxides as novel precursors of chiral 3-alkoxyimidazol-2-ylidenes derived from trans-1, 2-diaminocyclohexane and other chiral amino compounds. Molecules 2019, 24, 4398.10.3390/molecules24234398. - DOI - PMC - PubMed
    1. Ramla M. M.; Omar M. A.; El-Khamry A.-M. M.; El-Diwani H. I. Synthesis and antitumor activity of 1-substituted-2-methyl-5-nitrobenzimidazoles. Bioorg. Med. Chem. 2006, 14, 7324–7332. 10.1016/j.bmc.2006.06.033. - DOI - PubMed
    1. Handzlik J.; Szymańska E.; Nędza K.; Kubacka M.; Siwek A.; Mogilski S.; Handzlik J.; Filipek B.; Kieć-Kononowicz K. Pharmacophore models based studies on the affinity and selectivity toward 5-HT1A with reference to α1-adrenergic receptors among arylpiperazine derivatives of phenytoin. Bioorg. Med. Chem. 2011, 19, 1349–1360. 10.1016/j.bmc.2010.11.051. - DOI - PubMed
    1. Subtel’na I.; Atamanyuk D.; Szymańska E.; Kieć-Kononowicz K.; Zimenkovsky B.; Vasylenko O.; Gzella A.; Lesyk R. Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity. Bioorg. Med. Chem. 2010, 18, 5090–5102. 10.1016/j.bmc.2010.05.073. - DOI - PubMed