37904-23-7Relevant academic research and scientific papers
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
Zayed, Mohamed A.,El-Desawy, Mohamed,Eladly, Azza A.
, p. 1519 - 1536 (2019/09/18)
TWO amino)-4- NOVEL oxobut-2-enoic N-maleanilinic acid acid (p-MMA) derivatives and (I-II) (E) namely -4- ((4- (E) methoxy – oxo -4- ((4- phenyl) methyl amino)-4- phenyl) oxobut -2- enoic acid (p-MOMA) were prepared by solvent free reaction between maleic anhydride, 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. These 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.
Derivatives of aryl amines containing the cytotoxic 1,4-dioxo-2-butenyl pharmacophore
Jha, Amitabh,Mukherjee, Chandrani,Prasad, Ashok K.,Parmar, Virinder S.,Vadaparti, Manjula,Das, Umashankar,De Clercq, Erik,Balzarini, Jan,Stables, James P.,Shrivastav, Anuraag,Sharma, Rajendra K.,Dimmock, Jonathan R.
scheme or table, p. 1510 - 1515 (2010/06/16)
Several series of compounds containing the 1,4-dioxo-2-butenyl moiety have been prepared as candidate cytotoxins, including the methyl N-arylmaleamates, methyl N-arylfumaramates, and N-arylmaleimides. In addition, the N-arylisomaleimides were synthesized which are the structural isomers of N-arylmaleimides. These compounds were evaluated against human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 cells. Methyl N-arylfumaramates showed the highest cytotoxic potencies and, in particular, methyl N-(3,4-dichlorophenyl)fumaramate is six times more potent than melphalan towards L1210 cells and is equipotent with this drug in the Molt 4/C8 assay. Electrophilicity of compounds under investigation was demonstrated by carrying out thiolation using model benzyl mercaptan on representative compounds. Methyl N-(3,4-dichlorophenyl)fumaramate and methyl N-(4-chlorophenyl)maleamate inhibited human N-myristoyltransferase, a possible molecular target, in high micromolar range. QSAR and molecular modeling revealed some correlations between different structural features of a number of the molecules and cytotoxic potencies. Methyl N-arylfumaramates were well tolerated in mice in comparison to the analogs in other series of compounds tested. The data obtained in this investigation affords guidelines for preparing new series of molecules with greater potencies.
