Utility of amino acid coupled 1,2,4-triazoles in organic synthesis: synthesis of some new antileishmainal agents

El‐Saghier, Ahmed M. M.; Mohamed, Mounir A. A.; Abdalla, O. A.; Kadry, Asmaa M.

doi:10.4314/bcse.v32i3.14

Cited by 9 publications

(4 citation statements)

References 32 publications

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“…In keeping with our earlier efforts on the creation of a straightforward, universal technique for heterocyclic chemical synthesis to afford new derivatives, − we report here a fresh approach to the synthesis of imidazole-4-one and/or imidazolidin-4-one derivatives 4a–m through the reaction of different amines with ethylcyanoacetate and ethylglycinate hydrochloride in a sequential, one-pot, procedure under neat condition for 2 h at 70 °C (Scheme ).…”

Section: Resultsmentioning

confidence: 91%

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

El-Saghier,

Abdou,

Mohamed

et al. 2023

ACS Omega

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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).

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Section: Resultsmentioning

confidence: 91%

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

El-Saghier,

Abdou,

Mohamed

et al. 2023

ACS Omega

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“…Our goal in this work, which is a continuation of our work in heterocyclic synthesis, ,− is to synthesize new 1,3,4-thiadiazole and 1,3,4-thiadiazine bearing sulfamoylcarboxamide moiety with a variety of substitutions at position that, given the importance of systems, may act as active pharmacophores. In this study, we generated a new series of N -(4-sulfamoylphenyl)-6 H -1,3,4-thiadiazine-2-carboxamide and N -(4-sulfamoylphenyl)-1,3,4-thiadiazole-2-carboxamide derivatives 2 – 11 , as part of our ongoing research into the synthesis of new heterocycles.…”

Section: Resultsmentioning

confidence: 99%

Thiadiazole/Thiadiazine Derivatives as Insecticidal Agent: Design, Synthesis, and Biological Assessment of 1,3,4-(Thiadiazine/Thiadiazole)-Benzenesulfonamide Derivatives as IGRs Analogues against Spodoptera littoralis

El-Saghier,

Enaili,

Abdou

et al. 2024

J. Agric. Food Chem.

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In keeping with our investigation, a simple and practical synthesis of novel heterocyclic compounds with a sulfamoyl moiety that can be employed as insecticidal agents was reported. The compound 2-hydrazinyl-N-(4-sulfamoylphenyl)-2-thioxoacetamide 1 was coupled smoothly with triethylorthoformate or a variety of halo compounds, namely phenacyl chloride, chloroacetyl chloride, chloroacetaldehyde, chloroacetone, 1,3-dichloropropane, 1,2-dichloroethane, ethyl chloroformate, 2,3-dichloro-1,4-naphthoquinone, and chloroanil respectively, which afforded the 1,3,4-thiadiazole and 1,3,4-thiadiazine derivatives. The new products structure was determined using elemental and spectral analysis. Under laboratory conditions, the biological and toxicological effects of the synthetic compounds were also evaluated as insecticides against Spodoptera littoralis (Boisd.). Compounds 3 and 5 had LC50 values of 6.42 and 6.90 mg/L, respectively. The investigated compounds (from 2 to 11) had been undergoing molecular docking investigation for prediction of the optimal arrangement and strength of binding between the ligand (herein, the investigated compounds (from 2 to 11)) and a receptor (herein, the 2CH5) molecule. The binding affinity within docking score (S, kcal/mol) ranged between −8.23 (for compound 5), −8.12 (for compound 3) and −8.03 (for compound 9) to −6.01 (for compound 8). These compounds were shown to have a variety of binding interactions within the 2CH5 active site, as evidenced by protein–ligand docking configurations. This study gives evidence that those compounds have 2CH5-inhibitory capabilities and hence may be used for 2CH5-targeting development. Furthermore, the three top-ranked compounds (5, 3, and 9) and the standard buprofezin were subjected to density functional theory (DFT) analysis. The highest occupied molecular orbital–lowest unoccupied molecular orbital (HOMO–LUMO) energy difference (ΔE) of compounds 5, 3, and 9 was found to be comparable to that of buprofezin. These findings highlighted the potential and relevance of charge transfer at the molecular level.

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“…It estimates the probability of the molecule being active Pa and inactive Pi for all compounds. The consideration of Pa [21][22] values helps in the interpretation of prediction results.…”

Section: Biological Behaviormentioning

confidence: 99%

Synthesis, Characterization, and PASSS Inet Prediction of New Polyesters

Yehia

Khodairy

El-Remailya

et al. 2023

Sohag Journal of Sciences

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The interfacial polycondensation of indazole monomers 3 and 4 with various aromatic and aliphatic acid chlorides, including isophthaloyl-, terephthaloyl-, adipoyl-, and sebacoyl chloride, gave polyesters 5a-d and 6a-d containing an indazole moiety. The generated polyesters were categorized using elemental analysis, IR, 1 H-NMR, and MS spectra; XRD and Thermal Gravimetry analysis (TGA) examinations. Prediction of inflammatory biological behavior of selected polyesters using PASS Inet at Pa < 0.70, giving a high probability of anti-Gluconate 2-dehydrogenase (acceptor) inhibitor.

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Utility of amino acid coupled 1,2,4-triazoles in organic synthesis: synthesis of some new antileishmainal agents

Cited by 9 publications

References 32 publications

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

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

Thiadiazole/Thiadiazine Derivatives as Insecticidal Agent: Design, Synthesis, and Biological Assessment of 1,3,4-(Thiadiazine/Thiadiazole)-Benzenesulfonamide Derivatives as IGRs Analogues against Spodoptera littoralis

Synthesis, Characterization, and PASSS Inet Prediction of New Polyesters

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