Crystal structure and theoretical charge density studies of dilantin molecule

Kalaiarasi, Chinnasamy; Sangeetha, P.; Pavan, Mysore S.; Kumaradhas, Poomani

doi:10.1016/j.molstruc.2018.05.030

Cited by 10 publications

(8 citation statements)

References 55 publications

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“…The phenytoin anions behave as expected and bond lengths and angles are unexceptional and similar to those observed for the free acid (CSD refcode PHYDAN to PHYDAN03; Camerman & Camerman, 1971;Kalaiarasi et al, 2018;Moriyama et al, 2015;Chattopadhyay et al, 1993). Each anion is essentially planar.…”

Section: Resultssupporting

confidence: 62%

“…The structure of phenytoin as the free acid has been reported and described previously by several groups of authors [Cambridge Structural Database (CSD;Groom et al, 2016) refcodes PHYDAN to PHYDAN03 (Camerman & Camerman, 1971;Moriyama et al, 2015;Kalaiarasi et al, 2018;Chattopadhyay et al, 1993)]. The single-crystal structure of phenytoin sodium, however, has not yet been solved due to apparent challenges involving obtaining single crystals of suitable quality for XRD analysis.…”

Section: Introductionmentioning

confidence: 99%

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A threefold superstructure of the anti-epileptic drug phenytoin sodium as a mixed methanol solvate hydrate

et al. 2019

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Phenytoin sodium, a salt of 5,5‐diphenylimidazolidine‐2,4‐dione, or phenytoin, is commercially available in various dosage forms for its anti‐epileptic properties to treat and prevent seizures. The title compound, poly[aquatris(μ3‐4,4‐diphenyl‐2,5‐dioxoimidazolidin‐1‐ido)trimethanoltrisodium(I)], [Na3(C15H11N2O2)3(CH4O)3(H2O)1.08]n, a methanol solvate and hydrate of phenytoin sodium, forms a modulated crystal structure that consists of a supercell made up of three close‐to‐identical repeat units. Each of the basic fragments consists of one phenytoin anion, a sodium cation, and either a methanol, or a methanol and a water molecule coordinated to the sodium ion, yielding a formula unit of Na(C15H11N2O2)(CH3OH)x(H2O)y for each of the three segments (x, y = 0 or 1; x + y = 1 or 2). Modulation along the b axis is introduced due to the presence or absence of water or methanol molecules at sodium and by the alternating torsion angles of one of the two phenytoin phenyl rings. Individual segments within the asymmetric unit are linked by covalent Na—O and Na—N bonds, with each sodium ion coordinated to one anionic amide N atom and three keto O atoms. The Na—N and one of the Na—O bonds connect (C15H11N2O2)·Na units along the modulation direction, creating an infinite [(C15H11N2O2)·Na] chain that is further stabilized by intramolecular N—H…O hydrogen bonding parallel to [010]. The second Na—O bond connects this chain with a symmetry‐equivalent copy of itself created by a screw‐axis operation, yielding double strands of [(C15H11N2O2)·Na] chains. Two of these double strands, propagating in opposite directions, constitute the content of the unit cell. Neighboring double strands are connected with each other to form layers perpendicular to the a axis, tethered together via O—H…O hydrogen bonds involving the water and methanol molecules. In addition to modulation, each of the repeat units also exhibits disorder of the modulated segments. Phenyl rings of each repeat unit are rotationally disordered, and sodium‐coordinated methanol and water molecules are also positionally disordered and/or partially occupied. The solvated structure reported here, while not matching the patterns reported for any of the known forms of phenytoin sodium, does provide a first insight into the complications and complexities involved in resolving the structure of anhydrous phenytoin sodium.

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Section: Resultssupporting

confidence: 62%

Section: Introductionmentioning

confidence: 99%

A threefold superstructure of the anti-epileptic drug phenytoin sodium as a mixed methanol solvate hydrate

et al. 2019

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“…The calculated structural parameters (gas phase) are compared with reported (solid phase) crystallographic data (CCDC No: 1811138). 29 The comparison of theoretical and experimental geometrical parameters using linear regression coefficient (R 2 ) calculations is graphically represented in Figure 2. The R 2 shows the reliability of theoretical calculation, howbeit, a little bit deviation is observed.…”

Section: Structural Descriptionmentioning

confidence: 99%

Spectroscopic, density functional theoretical study, molecular docking, and in vitro studies based on anticancer activity studies against A₅₄₉ lung cancer cell line of diphenylhydantoin adsorbed on AuNPs surface

Shyni¹,

Leenaraj²,

Ittyachan

et al. 2021

J of Molecular Recognition

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The optimized geometry, FT-Raman, FT-IR, surface-enhanced Raman scattering, UV-Vis spectra, frontier molecular orbital analysis, molecular electrostatic potential analysis, and local and global reactivity descriptors of diphenylhydantoin (DPH) and diphenylhydantoin@AuNPs (DPHA) molecule have been investigated with the help of density functional theory method (B3LYP/6-31++G [d,p] together with LANL2DZ) and was compared and analyzed with the corresponding experimental data in order to identify their structural and bonding features responsible for their bioactivity. Insilico (molecular docking) biological activity screening of the molecules together with the in-vitro (SERS and MTT assay) analysis confirms the anticancer activity of DPH and DPHA molecules. The results of the structure-activity studies and bioactivity studies signify that the DPHA molecule is more active than the DPH molecule against lung cancer.

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“…The Hirshfeld surface of the crystal is being used to analyze the intermolecular interactions of the molecules in the crystal, which is de ned by using the weight function [the division of the sum of the promolecule density (spherical atom electron densities) to the sum of the same procrystal electron density [30,31]. The intermolecular contact information was obtained from the two d i parameters (distance from the surface to the nearest atom interior to the surface) and d e (distance from the surface to the nearest atom exterior to the surface), which is derived from the triangulation of surface points.…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Insights into the interactions between salt molecules: A combined experimental and computational study

Suresh

Kandasamy

Karthikeyan³

et al. 2021

Preprint

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The proton transfer (PT) complex of 2-amino 4-methoxy 6-methyl pyrimidinium (2A4M6MP) 4-aminosalicylate (4AMSA), C6H10ON3+ C7H6NO3−, (I), and 5-chlorosalicylate (5ClSA), C6H10ON3+ C7H4O3Cl− (II) were synthesized and crystallized. The crystal structures of both salt molecules were investigated by SC-XRD. Further, the calculated ∆pKa values clearly demonstrate that 2A4M6MP is a good salt former when combined with carboxylic acids. Hirshfeld surface analysis provides the quantifying interactions in the solid state and energy framework shows the stability of hydrogen bonding. QTAIM analysis reveals the nature of chemical bonding and electron density distribution of intermolecular interactions of pyrimidine based salt molecules.

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Crystal structure and theoretical charge density studies of dilantin molecule

Cited by 10 publications

References 55 publications

A threefold superstructure of the anti-epileptic drug phenytoin sodium as a mixed methanol solvate hydrate

A threefold superstructure of the anti-epileptic drug phenytoin sodium as a mixed methanol solvate hydrate

Spectroscopic, density functional theoretical study, molecular docking, and in vitro studies based on anticancer activity studies against A₅₄₉ lung cancer cell line of diphenylhydantoin adsorbed on AuNPs surface

Insights into the interactions between salt molecules: A combined experimental and computational study

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Crystal structure and theoretical charge density studies of dilantin molecule

Cited by 10 publications

References 55 publications

A threefold superstructure of the anti-epileptic drug phenytoin sodium as a mixed methanol solvate hydrate

A threefold superstructure of the anti-epileptic drug phenytoin sodium as a mixed methanol solvate hydrate

Spectroscopic, density functional theoretical study, molecular docking, and in vitro studies based on anticancer activity studies against A549 lung cancer cell line of diphenylhydantoin adsorbed on AuNPs surface

Insights into the interactions between salt molecules: A combined experimental and computational study

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Product

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Spectroscopic, density functional theoretical study, molecular docking, and in vitro studies based on anticancer activity studies against A₅₄₉ lung cancer cell line of diphenylhydantoin adsorbed on AuNPs surface