Crystal structure of 1,3-dimethyl-5-(2,4,6-trimethylbenzylidene)pyrimidine- 2,4,6-1H,3H,5H)-trione, C16H18N2O3

Barakat, Assem; Al‐Majid, Abdullah Mohammed; Al-Najjar, Hany J.; Choudhary, M. Iqbal; Yousuf, Sammer

doi:10.1515/ncrs-2014-0128

Cited by 8 publications

(9 citation statements)

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“…In the meanwhile, barbituric acid has been found to be associated with important biological activities including anti-hypertensive, anti-in ammatory, antitumor, anticonvulsant and hypnotic drugs [1][2][3][4][5][6][7][8][9][10][11][12]. We have succeeded to separate the active species which can act as nucleophile generated by aqueous diethylamine medium.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C₁₀H₁₉N₃O₃

Barakat

Ghabbour

Al‐Majid

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C₁₀H₁₉N₃O₃

Barakat

Ghabbour

Al‐Majid

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Additionally, barbituric acid derivatives exhibit antifungal, antimicrobial, antiviral, potential mushroom tyrosinase inhibition, antituberculosos, radio-sensitization, anticancer with anti-in ammatory activities, inhibition for diaminopimelate aminotransferase, and anti-proliferative activity [1][2][3][4][5][6][7][8][9][10][11][12][13].…”

Section: Discussionmentioning

confidence: 99%

“…"The molecules packing in the crystal structure is stabilized by two non-classical hydrogen bonds, of which O1 and O2 work as hydrogen bond acceptors and C9 and C11 work as hydrogen bond donors. The distance between C9-H9A· · · O1 i is 2.37 Å, C11-H11A· · · O2 ii is 2.41 Å and the angles are 167°and 171°, respectively" [7]. (Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+2, y−1, z.…”

Section: Discussionmentioning

confidence: 99%

“…The H atoms of the methyl groups were allowed to rotate with a xed angle around the C-C bond to best t the experimental electron density" [7].…”

Section: Methodsmentioning

confidence: 99%

“…Experimental details "C-bound H atoms were placed in calculated positions and were included in the re nement in the riding model approximation. The H atoms of the methyl groups were allowed to rotate with a xed angle around the C-C bond to best t the experimental electron density" [7].…”

Section: Source Of Materialsmentioning

confidence: 99%

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Crystal structure of 5-(3-fluorobenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; C₁₃H₁₁FN₂O₃

Barakat

Ghabbour

Al-Qahtani

et al. 2016

Zeitschrift Für Kristallographie - New Crystal Structures

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CCDC no.: 1452350The crystal structure is shown in the gure. Tables 1 and 2 contain details of the measurement method and a list of the atoms including atomic coordinates and displacement parameters. Source of materialA mixture of (1.0 mmol) 1,3-dimethylbarbituric acid and (1.0 mmol) 3-uorobenzaldehyde in 2.0 mL of H 2 O were charged into a 10 mL round bottom ask. The reaction mixture was stirred at room temperature for up to 30 min, until TLC showed complete consumption of both the reactants. After the completion of reaction, the solid product were collected by ltration and washed with 5 mL of water, and dried. 163.5, 162.2, 160.9, 160.2, 157.4, 151.2, 134.6, 129.8, 129.5, 119.8, 119.6, 119.4, 119.2, 29.2, 28.6. Experimental details"C-bound H atoms were placed in calculated positions and were included in the re nement in the riding model approximation. The H atoms of the methyl groups were allowed to rotate with a xed angle around the C-C bond to best t the experimental electron density" [7]. DiscussionBarbiturates show a wide range of pharmacological applications, such as general sedation, anesthesia,

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Synthesis and dynamics studies of barbituric acid derivatives as urease inhibitors

Barakat

Al‐Majid

Lotfy

et al. 2015

Chemistry Central Journal

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BackgroundDiscovery of potent inhibitors of urease (jack bean) enzyme is the first step in the development of drugs against diseases caused by ureolytic enzyme.ResultsThirty-two derivatives of barbituric acid as zwitterionic adducts of diethyl ammonium salts were synthesized. All synthesized compounds (4a–z and 5a–s) were screened for their in vitro inhibition potential against urease enzyme (jack bean urease). The compounds 4i (IC50 = 17.6 ± 0.23 µM) and 5l (IC50 = 17.2 ± 0.44 µM) were found to be the most active members of the series, and showed several fold more urease inhibition activity than the standard compound thiourea (IC50 = 21.2 ± 1.3 µM). Whereas, compounds 4a–b, 4d–e, 4g–h, 4j–4r, 4x, 4z, 5b, 5e, 5k, 5n–5q having IC50 values in the range of 22.7 ± 0.20 µM–43.8 ± 0.33 µM, were also found as potent urease inhibitors. Furthermore, Molecular Dynamics simulation and molecular docking studies were carried out to analyze the binding mode of barbituric acid derivatives using MOE. During MD simulation enol form is found to be more stable over its keto form due to their coordination with catalytic Nickel ion of Urease. Additionally, structural–activity relationship using automated docking method was applied where the compounds with high biological activity are deeply buried within the binding pocket of urease. As multiple hydrophilic crucial interactions with Ala169, KCX219, Asp362 and Ala366 stabilize the compound within the binding site, thus contributing greater activity.ConclusionsThis research study is useful for the discovery of economically, efficient viable new drug against infectious diseases.Graphical abstract:STD. Thiourea (IC50 = 21.2 ± 1.3 µM)Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-015-0140-1) contains supplementary material, which is available to authorized users.

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Crystal structure of 1,3-dimethyl-5-(2,4,6-trimethylbenzylidene)pyrimidine- 2,4,6-1H,3H,5H)-trione, C16H18N2O3

Cited by 8 publications

References 4 publications

Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C₁₀H₁₉N₃O₃

Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C₁₀H₁₉N₃O₃

Crystal structure of 5-(3-fluorobenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; C₁₃H₁₁FN₂O₃

Synthesis and dynamics studies of barbituric acid derivatives as urease inhibitors

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Crystal structure of 1,3-dimethyl-5-(2,4,6-trimethylbenzylidene)pyrimidine- 2,4,6-1H,3H,5H)-trione, C16H18N2O3

Cited by 8 publications

References 4 publications

Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C10H19N3O3

Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C10H19N3O3

Crystal structure of 5-(3-fluorobenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; C13H11FN2O3

Synthesis and dynamics studies of barbituric acid derivatives as urease inhibitors

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Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C₁₀H₁₉N₃O₃

Crystal structure of diethylammonium 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-ide, C₁₀H₁₉N₃O₃

Crystal structure of 5-(3-fluorobenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione; C₁₃H₁₁FN₂O₃