Author:
Anwer Kurls E.,Hamza Zeinab K.,Ramadan Ramadan M.
Abstract
AbstractEnaminonitrile pyridine derivative was used as a precursor for preparation of fourteen heterocyclic compounds using both conventional thermal and microwave techniques. Diverse organic reagents, such as chloroacetyl chloride, acetic anhydride, chloroacetic acid, carbon disulfide, p-toluene sulfonyl chloride, maleic anhydride, phthalic anhydride, were used. The chemical formulae and structures of isolated derivatives were obtained using different analytical and spectroscopic techniques such as IR, 1H-, 13C-NMR as well as mass spectrometry. The spectroscopic analyses revealed diverse structure arrangements for the products. Molecular structure optimization of certain compounds were performed by the density functional theory (DFT/B3LYP) method and the basis set 6–31 G with double zeta plus polarization (d,p). The antimicrobial inhibition and the antioxidant activity of the reported compounds were screened. Compounds 5, 6, 11 and 13 exhibited the highest antibacterial inhibition, while compound 8 gave the highest scavenging activity (IC50 43.39 µg/ml) against the DPPH radical. Structure–activity relationship of the reported compounds were correlated with the data of antibacterial and the antioxidant activity. The global reactivity descriptors were also correlated with the biological properties of compounds. The molecular docking studies of reported compounds were investigated, and the analysis showed that the docked compounds have highly negative values for the functional binding scores. The binding interaction was found to be correlated with the substituent fragments of the compounds.
Publisher
Springer Science and Business Media LLC
Reference51 articles.
1. Farag, A. A., Mohamed, E. A., Anwer, K. E., Azmy, E. A. & Sayed, G. H. Corrosion inhibition performance and computational studies of pyridine and pyran derivatives for API X-65 steel in 6 M H2SO4. J. Ind. Eng. Chem. 97, 523–538 (2021).
2. Henry, G. D. D. Novo synthesis of substituted pyridines. Tetrahedron 60, 6043–6061 (2004).
3. Jones, G. Comprehensive heterocyclic chemistry II. Pyridines and their benzo derivatives synthesis. Elsevier 5(05), 167–243 (1996).
4. Joseph, P. M. Quinoline, quinazoline and acridone alkaloids. Nat. Prod. Rep. 22, 627–646 (2005).
5. Movassaghi, M., Hill, M. D. & Ahmad, O. K. Direct synthesis of pyridine derivatives. J. Am. Chem. Soc. 129, 10096–10097 (2007).
Cited by
10 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
1. Development of benzenesulfonamide containing 1,2,3-triazole and 1,3,4-oxadiazole hybrids as cathepsin B inhibitors and DFT calculations;Journal of Molecular Structure;2025-01
2. Design, Synthesis, Antibacterial Activity, and Printing Performance of a Novel Class of Neocryptolpine Azo Disperse Dyes;Fibers and Polymers;2024-09-10
3. Guanidine hydrochloride assisted one-pot synthesis of 2-amino-4,6- disubstituted-3-cyanopyridine derivatives: a sustainable and greener strategy with catalyst recyclability;2024-09-03
4. Ultrasound promoted synthesis of 2-methylthio-3
H
-1,5-benzodiazepines using CaFe
2
O
4
NPs as heterogeneous catalyst and their
in-vitro
experimental and theoretical studies as antifungal agents;Journal of Sulfur Chemistry;2024-08-26
5. Catalyzed syntheses of novel series of spiro thiazolidinone derivatives with nano Fe2O3: spectroscopic, X-ray, Hirshfeld surface, DFT, biological and docking evaluations;Scientific Reports;2024-08-13