An efficient synthesis of 4,5-diaryl-3,4-dihydropyrimidin-2(1<i>H</i>)-one<i>via</i>a cesium carbonate-promoted direct condensation of 1-aryl-2-propanone with 1,1′-(arylmethylene)diurea

In this study, we report on antiproliferative benzyloxy dihydropyrimidinones (DHPMs) produced by the Biginelli reaction of benzyloxy benzaldehyde, urea, and diverse 1,3-diones. The reaction was catalyzed by lanthanum triflate and completed within 1-1.5 h, with 74-97% yield. The antiproliferative assay was carried out for all synthesized dihydropyrimidinones against six human solid tumor cell lines. Six compounds showed good antiproliferative activity with GI 50 values below 5 μM. Among all the synthesized compounds, the most potent derivative showed good antiproliferative activity against all cell lines with GI 50 values in the range of 1.1-3.1 μM. These DHPMs comply with druglikeness. Furthermore, ADMET prediction and the effect of P-glycoprotein on the antiproliferative activity were also studied. Overall, our method allows eco-friendly access to benzyloxy DHPMs as potential anticancer drugs.

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Synthesis and in vitro study of antiproliferative benzyloxy dihydropyrimidinones

Vala

Sharma

Patel

et al. 2021

Archiv der Pharmazie

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Transition-metal-free hydroamination/defluorination/cyclization of perfluoroalkyl alkynes with amidines

Sun

Luo

et al. 2022

Org. Chem. Front.

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Catalyst-free Approach to Dihydropyrimidones Using Glycerol/Ethyl Lactate as a Recyclable and Biodegradable Promoting Medium

Kushwaha,

Singh,

Baranwal

et al. 2024

LOC

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Abstract:: A variety of dihydropyrimidone compounds were synthesised using an effective one-pot, multicomponent, environmentally friendly reaction of aromatic aldehydes, urea/thiourea, ethyl acetoacetate, and glycerol/ethyl lactate. To the best of our knowledge, this is the first catalyst-free strategy for the synthesis of this key scaffold with medicinal chemistry applications. Other significant aspects of the current approach consist of the employment of glycerol/ethyl lactate as a biodegradable and environmentally friendly reaction medium-cum-promoter, the use of easily available substrates, moderate reaction conditions, ease of use, a wide substrate scope, a short reaction time, easy workup, and excellent yields, and atom efficiency, which make the disclosed procedure an excellent alternative to existing methods.

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An efficient synthesis of 4,5-diaryl-3,4-dihydropyrimidin-2(1H)-oneviaa cesium carbonate-promoted direct condensation of 1-aryl-2-propanone with 1,1′-(arylmethylene)diurea

Abstract: A Cs2CO3-promoted efficient method for the synthesis of 4,5-diaryl-3,4-dihydropyrimidin-2(1H)-one by using 1,1′-(arylmethylene)diurea and 1-aryl-2-propanone as substrates was developed.

Cited by 3 publications

References 53 publications

Synthesis and in vitro study of antiproliferative benzyloxy dihydropyrimidinones

Synthesis and in vitro study of antiproliferative benzyloxy dihydropyrimidinones

Transition-metal-free hydroamination/defluorination/cyclization of perfluoroalkyl alkynes with amidines

Catalyst-free Approach to Dihydropyrimidones Using Glycerol/Ethyl Lactate as a Recyclable and Biodegradable Promoting Medium

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