Chromeno[2,3-d]pyrimidine-triones Synthesis by a Three-Component Coupling Reaction

Ghahremanzadeh, Ramin; Fereshtehnejad, Fatemeh; Bazgir, Ayoob

doi:10.1248/cpb.58.516

Cited by 26 publications

(16 citation statements)

References 47 publications

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“…and C5, the latter being the most studied position. Within these structural modifications, various cyclization reactions at C5 and C6 of BA, thiobarbituric acid (TBA) and their derivatives (BADs and TBADs, respectively) [10][11][12][13][14][15][16][17][18][19] as well as at C5 with spiro formation [20][21][22][23][24] have been described. Interestingly, some of these transformations involve a multicomponent reaction (MCR) [11,14,16].…”

Section: Introductionmentioning

confidence: 99%

“…Within these structural modifications, various cyclization reactions at C5 and C6 of BA, thiobarbituric acid (TBA) and their derivatives (BADs and TBADs, respectively) [10][11][12][13][14][15][16][17][18][19] as well as at C5 with spiro formation [20][21][22][23][24] have been described. Interestingly, some of these transformations involve a multicomponent reaction (MCR) [11,14,16]. However, in most cases, the cyclization path is preceded by the formation of substituted methyl [10,18], arylidene [12,15,[19][20][21][22][23][24], or methylene [13,17,19] derivatives at C5 as key isolated or potential precursors of these modified pyrimidines.…”

Section: Introductionmentioning

confidence: 99%

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Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Figueiredo

Serrano

Cavalheiro

et al. 2018

European Journal of Medicinal Chemistry

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Barbituric and thiobarbituric acid derivatives have become progressively attractive to medicinal chemists due to their wide range of biological activities. Herein, different series of 1,3,5-trisubstituted barbiturates and thiobarbiturates were prepared in moderate to excellent yields and their activity as xanthine oxidase inhibitors, antioxidants, antibacterial agents and as anti-proliferative compounds was evaluated in vitro. Interesting bioactive barbiturates were found namely, 1,3-dimethyl-5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6c) and 1,3-dimethyl-5-[1-[2-(4-nitrophenyl)hydrazinyl]ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6e), which showed concomitant xanthine oxidase inhibitory effect (IC values of 24.3 and 27.9 μM, respectively), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity (IC values of 18.8 and 23.8 μM, respectively). In addition, 5-[1-(2-phenylhydrazinyl)ethylidene]pyrimidine-2,4,6(1H,3H,5H)-trione (6d) also revealed DPPH radical scavenger effect, with an IC value of 20.4 μM. Moreover, relevant cytotoxicity against MCF-7 cells (IC = 13.3 μM) was observed with 5-[[(2-chloro-4-nitrophenyl)amino]methylene]-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (7d). Finally, different 5-hydrazinylethylidenepyrimidines revealed antibacterial activity against Acinetobacter baumannii (MIC values between 12.5 and 25.0 μM) which paves the way for developing new treatments for infections caused by this Gram-negative coccobacillus bacterium, known to be an opportunistic pathogen in humans with high relevance in multidrug-resistant nosocomial infections. The most promising bioactive barbiturates were studied in silico with emphasis on compliance with the Lipinski's rule of five as well as several pharmacokinetics and toxicity parameters.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Figueiredo

Serrano

Cavalheiro

et al. 2018

European Journal of Medicinal Chemistry

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“…Pyrazole and pyrazole-based derivatives have been reported as potential CB2 receptor ligands with antagonist/inverse agonist properties [16], dual inhibition of CCR5/CXCR4 HIV entry [17], and reverse transcriptase HIV-1 non-nucleoside reverse transcriptase inhibitors [18]. Pyrimidine-2,4,6-trione derivatives are an important class of nitrogen heterocycles that have attracted more attention in the last decade: due to their use as a precursor for the construction of condensed heterocyclic systems, they represent an interesting pharmacophore for pharmaceutical products [19,20,21,22,23,24,25,26,27,28,29,30,31,32]. They have utility as anticancer agents, enzyme inhibitors, neuromodulators, antibiotics, herbicides, and plant growth regulators, antibacterial, and anti-oxidant agents (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrazole-Thiobarbituric Acid Derivatives: Antimicrobial Activity and Docking Studies

et al. 2016

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A one-pot reaction was described that results in various pyrazole-thiobarbituric acid derivatives as new pharmacophore agents. These new heterocycles were synthesized in high yields with a broad substrate scope under mild reaction conditions in water mediated by NHEt 2 . The molecular structures of the synthesized compounds were assigned based on different spectroscopic techniques. The new compounds were evaluated for their antibacterial and antifungal activity. Compounds 4h and 4l were the most active compounds against C. albicans with MIC = 4 µg/L. Compound 4c exhibited the best activity against S. aureus and E. faecalis with MIC = 16 µg/L. However, compounds 4l and 4o were the most active against B. subtilis with MIC = 16 µg/L. Molecular docking studies for the final compounds and standard drugs were performed using the OpenEye program.

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“…Yield: 95%; white solid; 161 °C; FTIR (KBr)

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(cm −1 ): 3478, 2936, 2864, 1683; 1 H NMR (DMSO‐d6, 400 MHz) δ (ppm): 0.96 (3H, s, CH3), 1.13 (3H, s, CH3), 2.11–2.57 (4H, m, 2CH 2 ), 4.56 (1H, s, CH), 7.16–7.23 (5H, m, H‐Ar), 11.03 (1H, s, NH), 12.12 (1H, brs, NH).…”

Section: Methodsmentioning

confidence: 99%

Green and rapid synthesis of dihydropyrimido [4,5‐b]quinolinetrione derivatives using CoFe₂O₄@PPA as high efficient solid acidic catalyst under ultrasonic irradiation

Moradi

Mahdipour

2019

Applied Organom Chemis

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A new high efficient and green protocol for the preparation of dihydropyrimido [4,5-b]quinolinetrione derivatives using magnetically solid acid catalyst was presented. High performance solid acid catalyst was prepared through a three-step reaction. Firstly, CoFe 2 O 4 nano particles were synthesized using co-precipitation method. In second step, CoFe 2 O 4 nano particles were coated with SiO 2 shell through treatment with tetraethyl orthosilicate (CoFe 2 O 4 @SiO 2 ). Finaly, CoFe 2 O 4 @SiO 2 was modified with polyphosphoric acid (CoFe 2 O 4 @SiO 2 /PPA) in a simple manner. Green reusable catalyst was characterized in details using FTIR, VSM, TEM, FESEM, EDX and used as catalyst for the synthesis of dihydropyrimido[4,5-b]quinolinetrione derivatives.Reaction was performed under ultrasonic irradiation as green, effective and mild conditions and products were achieved in high to excellent yields.Green and eco-friendly conditions, short reaction times with high yield of products in addition to easy workup are some merits of presented method. KEYWORDSCoFe 2 O 4 @SiO 2 /PPA, dihydropyrimido[4,5-b]quinolinetrione, green chemistry, solid acidic catalyst, ultrasonic irradiation

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Chromeno[2,3-d]pyrimidine-triones Synthesis by a Three-Component Coupling Reaction

Cited by 26 publications

References 47 publications

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Synthesis of Pyrazole-Thiobarbituric Acid Derivatives: Antimicrobial Activity and Docking Studies

Green and rapid synthesis of dihydropyrimido [4,5‐b]quinolinetrione derivatives using CoFe₂O₄@PPA as high efficient solid acidic catalyst under ultrasonic irradiation

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Chromeno[2,3-d]pyrimidine-triones Synthesis by a Three-Component Coupling Reaction

Cited by 26 publications

References 47 publications

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Trisubstituted barbiturates and thiobarbiturates: Synthesis and biological evaluation as xanthine oxidase inhibitors, antioxidants, antibacterial and anti-proliferative agents

Synthesis of Pyrazole-Thiobarbituric Acid Derivatives: Antimicrobial Activity and Docking Studies

Green and rapid synthesis of dihydropyrimido [4,5‐b]quinolinetrione derivatives using CoFe2O4@PPA as high efficient solid acidic catalyst under ultrasonic irradiation

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Green and rapid synthesis of dihydropyrimido [4,5‐b]quinolinetrione derivatives using CoFe₂O₄@PPA as high efficient solid acidic catalyst under ultrasonic irradiation