Biological activity of dihydropyrimidinone (DHPM) derivatives: A systematic review

Matos, Larizza Hellen Santana; Masson, Flávia Teixeira; Simeoni, Luiz Alberto; Homem-de-Mello, Maurício

doi:10.1016/j.ejmech.2017.10.073

Cited by 174 publications

(95 citation statements)

References 135 publications

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“…Pyrimidine analogs are an integral part of several biologically active molecules such as natural products and nucleic acids. Moreover, this kind of heterocyclic compound finds several therapeutic applications in medicinal chemistry as an essential building block of a large variety of drug candidates and nucleic acids, with a structural resemblance to purines [99,100]. Recently, the US-FDA approved some pyrimidine and pyrimidinone derivatives (ibrutinib, capecitabine, folinic acid and monastrol) as anticancer agents (Figure 48) [18].…”

Section: Pyrimidinesmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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The analogs of nitrogen-based heterocycles occupy an exclusive position as a valuable source of therapeutic agents in medicinal chemistry. More than 75% of drugs approved by the FDA and currently available in the market are nitrogen-containing heterocyclic moieties. In the forthcoming decade, a much greater share of new nitrogen-based pharmaceuticals is anticipated. Many new nitrogen-based heterocycles have been designed. The number of novel N-heterocyclic moieties with significant physiological properties and promising applications in medicinal chemistry is ever-growing. In this review, we consolidate the recent advances on novel nitrogen-containing heterocycles and their distinct biological activities, reported over the past one year (2019 to early 2020). This review highlights the trends in the use of nitrogen-based moieties in drug design and the development of different potent and competent candidates against various diseases.

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Section: Pyrimidinesmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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“…The present study is part of an ongoing endeavour in the polymorphic screening of substituted dihydropyrimidinone carboxylate derivatives. This class of compounds falls into a well-studied category of dihydropyrimidine derivatives, which are reported to have a wide range of properties, including antitumoural, antitubercular, anti-inflammatory and antiviral, to name but a few (Kappe et al, 1997;Mayer et al, 1999;Matos et al, 2018;Venugopala et al, 2016). A greener protocol in solvent-free and catalyst-free environments under easily controllable conditions was used for the synthesis.…”

Section: Introductionmentioning

confidence: 99%

Crystal structures of the anhydrous and two solvated forms of methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

et al. 2020

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Methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate, (I), was found to exhibit solvatomorphism. The compound was prepared using a classic Biginelli reaction under mild conditions, without using catalysts and in a solvent-free environment. Single crystals of two solvatomorphs and one anhydrous form of (I) were obtained through various crystallization methods. The anhydrous form, C13H13FN2O3, was found to crystallize in the monoclinic space group C2/c. It showed one molecule in the asymmetric unit. The solvatomorph with included carbon tetrachloride, C13H13FN2O3·0.25CCl4, was found to crystallize in the monoclinic space group P2/n. The asymmetric unit revealed two molecules of (I) and one disordered carbon tetrachloride solvent molecule that lies on a twofold axis. A solvatomorph including ethyl acetate, C13H13FN2O3·0.5C4H8O2, was found to crystallize in the triclinic space group P\overline{1} with one molecule of (I) and one solvent molecule on an inversion centre in the asymmetric unit. The solvent molecules in the solvatomorphs were found to be disordered, with a unique case of crystallographically induced disorder in (I) crystallized with ethyl acetate. Hydrogen-bonding interactions, for example, N—H...O=C, C—H...O=C, C—H...F and C—H...π, contribute to the crystal packing with the formation of a characteristic dimer through N—H...O=C interactions in all three forms. The solvatomorphs display additional interactions, such as C—F...N and C—Cl...π, which are responsible for their molecular arrangement. The thermal properties of the forms were analysed through differential scanning calorimetry (DSC), hot stage microscopy (HSM) and thermogravimetric analysis (TGA) experiments.

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“…Furthermore, the pharmacological effect of DHPMs has been widely investigated, mainly focusing on anticancer drug development [3]. Monastrol is a DHPM identified as a kinesin-5 inhibitor, involved in the separation of genetic material during mitosis.…”

Section: Introductionmentioning

confidence: 99%

Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Gonçalves

Azambuja

Davi

et al. 2019

Molbank

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The Biginelli reaction is an acid-catalyzed, three-component reaction between an aldehyde, a hydrogen methylene active compound, and urea (or its analogue) and constitutes a rapid and easy synthesis of highly functionalized heterocycles. Synthesis of ethyl 6-methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate, identified by our laboratory code LaSOM® 293, was achieved using the Biginelli reaction as the key step, followed by the Huisgen 1,3-dipolar cycloaddition in a convergent four-step route. The product LaSOM® 293 was obtained with a yield of 84%.

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Biological activity of dihydropyrimidinone (DHPM) derivatives: A systematic review

Cited by 174 publications

References 135 publications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

Crystal structures of the anhydrous and two solvated forms of methyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Ethyl 6-Methyl-2-oxo-4-{4-[(1-phenyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1,2,3,4-tetrahydropyrimidine-5-carboxylate

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