Spectroscopic Investigation of Para-Methyl and Para-Methoxy Maleanilinic Acids in Comparison with Thermal Analyses and Theoretical Calculations and Evaluation of Cytotoxicity Against Carcinoma Cells | ||||
| Egyptian Journal of Chemistry | ||||
| Article 13, Volume 62, Issue 8, August 2019, Page 1519-1536 PDF (1.74 MB) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2019.7353.1597 | ||||
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| Authors | ||||
mohamed A. Zayed   1; Mohamed El-Desawy2; AZZA Eladly3
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| 1Department of chemistry, Faculty of Science, Cairo University (D.Sc. Anal.Chem.) | ||||
| 2Nuclear Physics Department, Nuclear Research center, AEA, 13759-Cairo, Egypt | ||||
| 3Science and Technology Center of Excellence, Military production , M P P, P.O.Box 3066, Elsalam II, Cairo, Egypt | ||||
| Abstract | ||||
| Two novel N-maleanilinic acid derivatives (I-II) namely (E) – oxo -4- ((4- methyl phenyl) amino)-4- oxobut-2-enoic acid (p-MMA) and (E) -4- ((4- methoxy phenyl) amino)-4- oxobut -2- enoic acid (p-MOMA) were prepared by solvent free reaction between maleic anhydride and a p- methyl and p-methoxy aniline derivatives in a good yield. These compounds were synthesized and investigated using elemental analyses, FT-IR and thermal analyses under argon atmosphere. The crystallographic structures of studied compounds were investigated by X-ray diffraction (XRD). The molecular structures of the titled compounds in the ground state were optimized by DFT/B3LYP and HF methods with 6-311G++ (d,p) basis set. Calculations were carried out by GAUSSIAN 09 suite of programs. Natural bond orbitals (NBO) analysis and frontier molecular orbitals were performed using NBO 3.1 program implemented in the Gaussian 09 package are presented at the same level of theory. Thesis results were tabulated. This research aims chiefly to correlate between the structures of these investigated derivatives using experimental techniques in comparison with the theoretical molecular orbital (MO) calculated parameters. This correlation between experimental and theoretical calculations provided a good confirmation of the proposed structures of the newly prepared compounds. The derivatives were found to be highly effective against Hepatocellular carcinoma cells > Breast carcinoma cells > colon carcinoma cells. It was recognized, that cancer cells over expression promotes tumorigenic functions; were suppressed by p-MMA > p-MOMA inhibitors. | ||||
| Keywords | ||||
| N-maleanilinic acids; spectroscopy (FT-IR); thermal analyses; XRD; DFT calculations; biological activity against Carcinoma cells | ||||
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