New multi-functionalized pyridines: Facile synthesis, anti-cancer evaluation and in silico molecular docking [2025-10-04]
Developing new compounds with bioactivity, especially against tumors, targeting G-quadruplexes is of great importance. In this direction,
some new phthalimide-incorporating pyridine derivatives were synthesized using the phthalimido-acetophenone derivative 1 as a key precursor.
Three-component cyclocondensation of compound 1 with various aryl aldehydes and ethyl cyanoacetate or malononitrile utilizing ammonium
acetate as the nitrogen source afforded the 4-substituted-6-(4-phthalimidophenyl)pyridin-2-one-3-carbonitriles 2a-e or the 2-amino-4-
substituted-6-(4-phthalimidophenyl)pyridine-3-carbonitriles 3a,b, respectively. Moreover, the characterization of these derivatives was
identified on the basis of elemental analysis and spectroscopic tools. Additionally, the potency of the targeted molecules as anticancer agents
was assessed against two carcinogenic human cell lines, namely, colon cancer (HCT-116) and human prostate cancer (PC3) cells. They exhibited
promising cytotoxicity in which compounds 2a and 2b have the strongest potency comparable with doxorubicin (Dox). The conducted molecular
docking studies revealed a good correlation between the anti-cancer activities of compounds and their binding effectiveness with both c-MYC
and KRAS G-quadruplexes.
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Green and facile synthesis of pyrimidine derivatives using chloride chloride-urea mixture as a deep eutectic solvent or cerium (IV) ammonium nitrate [2019-06-24]
An efficient and facile synthesis of substituted pyrimidine derivatives through Biginelli type reaction was achieved in high yields via one-pot reaction of aromatic aldehydes, active methylene compounds and urea or thiourea in the presence of choline chloride-urea mixture as a deep eutectic solvent or cerium (IV) ammonium nitrate (CAN) as a catalyst at different conditions. The reaction was carried out using different ratio of CAN in different solvents to determine the optimum conditions. In addition, 2-mercapto-6-oxo-4-(thiophen-2-yl)-1,6-dihydropyrimidine-5-carbonitrile was employed in the synthesis of pyrimidinylhydrazide and its corresponding hydrazone. The Structural formula of all derivatives were confirmed and characterized by their elemental analyses and spectral data (IR, MS, 1H NMR, 13C NMR). download attachment |
