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Search Results (3)

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Keywords = dihydro-pyrimidinone-2-thione

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13 pages, 656 KB  
Article
Synthesis and Antioxidant Activity of Novel Biginelli Adducts with Phenolic Fragments
by Olga V. Snastina, Erik R. Sabitov, Viktoria A. Kuricheva and Vladimir N. Koshelev
Appl. Sci. 2025, 15(16), 9152; https://doi.org/10.3390/app15169152 - 20 Aug 2025
Viewed by 1552
Abstract
In this work, eco-friendly ceric ammonium nitrate (CAN) and ferric chloride hexahydrate catalysts in ethanol/acetonitrile systems were used to efficiently synthesize novel dihydropyrimidinone (-thione) derivatives via the Biginelli reaction. The obtained compounds with phenolic fragments at the C4 position demonstrated enhanced antioxidant properties. [...] Read more.
In this work, eco-friendly ceric ammonium nitrate (CAN) and ferric chloride hexahydrate catalysts in ethanol/acetonitrile systems were used to efficiently synthesize novel dihydropyrimidinone (-thione) derivatives via the Biginelli reaction. The obtained compounds with phenolic fragments at the C4 position demonstrated enhanced antioxidant properties. Significant structure–activity relationships were indicated by three complementary assays (PFRAP, ABTS, and AAPH-induced DNA oxidation): oxo-derivatives demonstrated superior ferric ion reduction (PFRAP), while thio-substituted analogs consistently outperformed their carbonyl counterparts in radical scavenging. Remarkably, all compounds surpassed the reference antioxidant BHT, demonstrating the potential of synthesized dihydropyrimidine structures as multifunctional antioxidants for therapeutic applications. The study also shows the relationship between the catalyst–solvent system and its effect on product yields, using ceric ammonium nitrate and ferric chloride hexahydrate. Full article
(This article belongs to the Section Chemical and Molecular Sciences)
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4 pages, 348 KB  
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Ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
by Itamar Luís Gonçalves, Luciano Porto Kagami, Gustavo Machado das Neves, Liliana Rockenbach, Leonardo Davi, Alceu Felipe Soares, Solange Cristina Garcia and Vera Lucia Eifler-Lima
Molbank 2018, 2018(4), M1029; https://doi.org/10.3390/M1029 - 13 Nov 2018
Cited by 1 | Viewed by 4095
Abstract
The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using [...] Read more.
The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using a functionalized thiourea. In silico studies demonstrated that the compound title showed good potential for interacting with ecto-5’-nucleotidase, which has been considered as a target in designs for anti-cancer drugs. Full article
(This article belongs to the Special Issue Molecules from Multicomponent Reactions)
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10 pages, 85 KB  
Article
Synthesis and Cyclizations of N-(2,3-, 3,4- and 3,5-Dimethylphenyl)-β-alanines
by Rita Vaickelioniene, Vytautas Mickevicius and Gema Mikulskiene
Molecules 2005, 10(2), 407-416; https://doi.org/10.3390/10020407 - 28 Feb 2005
Cited by 14 | Viewed by 8576
Abstract
A series of 1-aryl substituted dihydro-, 5-methyldihydro- and 6-methyl-dihydro-2,4(1H,3H)pyrimidinediones and their 2-thio analogues were obtained byreaction of the corresponding β-alanines or α-methyl- and β-methyl-β-alanines with ureaor potassium thiocyanate. The reaction of N-(2,3- and 3,5-dimethylphenyl)-α-methyl-β-alanines with ethyl acetoacetate gave 1-(2,3- or 3,5-dimethylphenyl)-2,5-dimethyl-1,4,5,6-tetrahydro-4(1H)pyridones. The combined [...] Read more.
A series of 1-aryl substituted dihydro-, 5-methyldihydro- and 6-methyl-dihydro-2,4(1H,3H)pyrimidinediones and their 2-thio analogues were obtained byreaction of the corresponding β-alanines or α-methyl- and β-methyl-β-alanines with ureaor potassium thiocyanate. The reaction of N-(2,3- and 3,5-dimethylphenyl)-α-methyl-β-alanines with ethyl acetoacetate gave 1-(2,3- or 3,5-dimethylphenyl)-2,5-dimethyl-1,4,5,6-tetrahydro-4(1H)pyridones. The combined spectral data obtained by 1H-, 13C-,1 H/13C (HETCOR) NMR and IR provided useful information about the structure of theproducts synthesized in this work. Full article
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