A facile synthesis of new coumarin-3,4-dihydropyrimidin-2(1H)-ones/thiones dyads

Benazzouz, Amina; Makhloufi‐Chebli, Malika; Khatir–Hamdi, Nejla; Boutemeur-Khedis, Baya; Silva, Artur M. S.; Hamdi, Maâmar

doi:10.1016/j.tet.2015.04.028

Cited by 21 publications

(19 citation statements)

References 20 publications

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“…The Biginelli reaction [ 27 , 28 , 29 ] is an important MCR [ 30 ] because the products exhibit a wide range of biological activities. An acid-catalyzed Biginelli reaction involving a one-pot three component condensation of furochromone carbaldehyde ( 1 ), Curcumin ( 2 ), and urea/thiourea gave compounds 8a , b ( Scheme 5 ).…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

et al. 2018

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Curcumin, a widely utilized flavor and coloring agent in food, has been shown to demonstrate powerful antioxidant, antitumor promoting and anti-inflammatory properties in vitro and in vivo. In the present work, synthesis of new heterocyclic derivatives based on Curcumin was studied. Compound 3 was synthesized via the reaction of furochromone carbaldehyde (1) with Curcumin (2) using pipredine as catalyst. Also, novel, 4,9-dimethoxy-5H-furo [3, 2-g] chromen-5-one derivatives 4a–d, 6a–d, 7, 8a–d, 9 and 10 were synthesized by the reactions of furochromone carbaldehyde (1) with different reagents (namely: appropriate amine 3a–d, appropriate hydrazine 5a–d, hydroxylamine hydrochloride, urea/thiourea, malononitrile, malononitrile with hydrazine hydrate). The structure of the synthesized products had been confirmed from their spectroscopic data (IR, 1H-NMR, 13C-NMR and mass spectra). In the present investigation, the newly synthesized products were screened using the MTT colorimetric assay for their in vitro inhibition capacity in two human cancer cell lines (hepatocellular carcinoma (HEPG2) and breast cancer (MCF-7) as well as the normal cell line (human normal melanocyte, HFB4) in comparison to the known anticancer drugs: 5-flurouracil and doxorubicin. The anticancer activity results indicated that the synthesized products 4c and 8b showed growth inhibition activity against HEPG2 cell line and synthesized products 4b and 8a showed growth inhibition activity against MCF-7, but with varying intensities in comparison to the known anticancer drugs, 5-flurouracil and doxorubicin. Cyclin dependent kinase 2 (CDK2), a major cell cycle protein, was identified as a potential molecular target of Curcumin. Furthermore, Curcumin induced G1 cell cycle arrest, which is regulated by CDK2 in cancer cells. Therefore, we used molecular modelling to study in silico the possible inhibitory effect of CDK2 by Curcumin derivatives as a possible mechanism of these compounds as anticancer agents. The molecular docking study revealed that compounds 4b, 8a and 8b were the most effective compounds in inhibiting CDk2, and, this result was in agreement with cytotoxicity assay.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

et al. 2018

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“…In the presence of melamine-modified chitosan (Cs-Pr-Me) materials as a reusable bifunctional organocatalyst, Valiey et al [94] performed a green protocol to synthesize benzylpyrazolyl coumarin derivatives by reacting arylaldehydes, ethyl acetoacetate, hydrazine derivatives, malononitrile and 4-hydroxycoumarin, Scheme 67. Hamdi et al [95] synthesized 4-aryl-6-methyl-5-(2-oxo-2Hchromene-3-carbonyl)-3,4-dihydropyrimidin-2(1H)-one / thiones from 3-acetoacetylcoumarin, benzaldehyde and urea/thiourea in CH 3 CN in the presence of sulfuric acid, Scheme 68.…”

Section: Coumarin As a Precursor In Multicomponent Reactionsmentioning

confidence: 99%

“…In the presence of melamine‐modified chitosan (Cs‐Pr‐Me) materials as a reusable bifunctional organocatalyst, Valiey et al [94] . performed a green protocol to synthesize benzylpyrazolyl coumarin derivatives by reacting arylaldehydes, ethyl acetoacetate, hydrazine derivatives, malononitrile and 4‐hydroxycoumarin, Scheme 67.…”

Section: Coumarin Synthesismentioning

confidence: 99%

Synthesis and Biological Properties of Coumarin Derivatives. A Review

et al. 2021

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Coumarin and its derivatives are widely used as scaffolds in the synthesis of new heterocyclic systems. This review focuses on current developments in the synthesis of heterocyclic coumarin compounds. Numerous approaches especially involving nanoparticle catalysts have been developed to get new bioactive coumarin derivatives endowed with pharmacological and biological activities. The present work describes the reactivity and the new strategies using various catalysts for the synthesis of coumarin and its derivatives reported in the literature and their biological properties.

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“…This property of cyclodextrin is utilized in various applications [33,34]. Benazzouz et al described a simple and efficient synthetic startegy for a new series of 4-aryl-6-methyl-5-(2-oxo-2Hchromene-3-carbonyl)-3,4-dihydropyrimidin-2(1H)ones/thiones 22 or 23 [35]. The reaction was initiated using 3-(acetoacetyl) coumarin derivatives as key synthon 21, parasubstituted benzaldehyde 1 and urea/thiourea 3 in the presence of sulfuric acid, acting as a catalyst, under refluxing acetonitrile.…”

Section: Synthetic Strategiesmentioning

confidence: 99%

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

Kaur

Chaudhary

Kumar

et al. 2017

European Journal of Medicinal Chemistry

249

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Dihydropyrimidines are the most important heterocyclic ring systems which play an important role in the synthesis of DNA and RNA. Synthetically they were synthesized using Multi-component reactions like Biginelli reaction and Hantzschdihydropyridine. In the past decades, such Biginelli type dihydropyrimidones have received a considerable amount of attention due to the interesting pharmacological properties associated with this heterocyclic scaffold. In this review, we highlight recent developments in this area, with a focus on the DHPMs, recently developed as anti-inflammatory, anti-HIV, anti-tubercular, antifungal anticancer, antibacterial, antifilarial, antihyperglycemic, antihypertensive, analgesic, anti-convulsant, antioxidant, anti-TRPA1, anti-SARS, and anti-cancer activity and α binding affinity.

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A facile synthesis of new coumarin-3,4-dihydropyrimidin-2(1H)-ones/thiones dyads

Cited by 21 publications

References 20 publications

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

Design, Synthesis, Anticancer Evaluation and Docking Studies of Novel Heterocyclic Derivatives Obtained via Reactions Involving Curcumin

Synthesis and Biological Properties of Coumarin Derivatives. A Review

Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review

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