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Volume 29, Issue 10
  • ISSN: 1385-2728
  • E-ISSN: 1875-5348

Abstract

A series of sixteen new 4-(substituted phenyl)-6-(substituted phenylamino)-3,4-dihydropyrimidine-2(1)-one/thione derivatives have been synthesized in two-step reaction. In the first step, chalcones () were obtained, and in the second step, these chalcones were reacted with urea and thiourea in the presence of potassium hydroxide to obtain the corresponding pyrimidinones and thiopyrimidinones. The progress of reaction was monitored by means of TLC (visualized it in Iodine chamber), The structures of the synthesized compounds 4-(substituted phenyl)-6-(substituted phenylamino)-3,4-dihydropyri-midine-2(1)-ones/thione derivatives were investigated by IR, mass, 1H-NMR spectral and elemental analysis. The title compounds were evaluated for anti-inflammatory and antioxidant activity. Anti-inflammatory activity was carried out using the carrageenan-induced rat-paw edema method and compared with standard drug diclofenac sodium. Antioxidant activity was measured using the DPPH, FRAP, and hydrogen peroxide (HO) method and compared with standard ascorbic acid. Electron-donating groups showed better antioxidant activity than electron-withdrawing ones in both series. All the compounds exhibited good to moderate activity. Compound showed better antioxidant activity, and compound exhibited better anti-inflammatory activity, while compound showed minimum antioxidant as well as anti-inflammatory activities than other compounds. To better understand, molecular docking studies were performed. The molecular docking studies revealed that all synthesized compounds showed good receptor binding interaction in which compound had the highest docking score of 9.8 due to interaction with CYS36, PRO153, TYR130, GLY45, LEU152, ARG469, LYS468, and GLU465.

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2024-09-16
2025-06-18

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/content/journals/coc/10.2174/0113852728301326240827115106
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3,4-Dihydropyrimidine-2(1H)-one/thione Derivatives as Anti-inflammatory and Antioxidant Agents: Synthesis, Biological activity, and Docking Studies
Current Organic Chemistry 29, 814 (2025); https://doi.org/10.2174/0113852728301326240827115106
/content/journals/coc/10.2174/0113852728301326240827115106
/content/journals/coc/10.2174/0113852728301326240827115106
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  • Article Type:     Research Article
Keyword(s): 3,4-Dihydropyrimidine-2(1H)-ones/thione; anti-inflammatory activity; antioxidant activity; DPPH assay; FRAP activity; hydrogen peroxide

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