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Journal articles on the topic '5-alkoxy- and aryloxymethyl-5-(2-thienyl) hydantoins'

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Published: 4 June 2021

Last updated: 15 February 2022

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1

Martínez-Gómez, Ana Isabel, Sergio Martínez-Rodríguez, Josefa María Clemente-Jiménez, Joaquín Pozo-Dengra, Felipe Rodríguez-Vico, and Francisco Javier Las Heras-Vázquez. "Recombinant Polycistronic Structure of Hydantoinase Process Genes in Escherichia coli for the Production of Optically Pure d-Amino Acids." Applied and Environmental Microbiology 73, no. 5 (2007): 1525–31. http://dx.doi.org/10.1128/aem.02365-06.

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ABSTRACT Two recombinant reaction systems for the production of optically pure d-amino acids from different d,l-5-monosubstituted hydantoins were constructed. Each system contained three enzymes, two of which were d-hydantoinase and d-carbamoylase from Agrobacterium tumefaciens BQL9. The third enzyme was hydantoin racemase 1 for the first system and hydantoin racemase 2 for the second system, both from A. tumefaciens C58. Each system was formed by using a recombinant Escherichia coli strain with one plasmid harboring three genes coexpressed with one promoter in a polycistronic structure. The d

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2

Keiko, N. A., T. A. Kuznetsova, N. V. Vchislo, Yu A. Chuvashev, L. I. Larina, and M. G. Voronkov. "Synthesis of new 5-substituted hydantoins from 2-alkoxy-1-cyano-1-trimethylsiloxypropenes." Russian Journal of General Chemistry 77, no. 12 (2007): 2145–49. http://dx.doi.org/10.1134/s1070363207120122.

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3

Ahmad, Roshan, Rukhsana Jabeen, Mohammad Zia-ul-Haq, Humaira Nadeem, Helmut Duddeck, and Eugen J. Verspohl. "Chiral Aryl Sulfonyl Hydantoins as Hypoglycemic Agents." Zeitschrift für Naturforschung B 55, no. 2 (2000): 203–7. http://dx.doi.org/10.1515/znb-2000-0212.

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Some novel chiral sulfonyl hydantoin derivatives 2a-e and 3 a-e have been prepared. p-Toluenesulfonyl chloride on treatment with L-amino acids in presence of K2CO3/H2O yielded N-(p-toluensulfonyl-)amino acids 1a - e which were cyclized in presence of NH4-SCN Ac2O to afford 1-(p-toluenesulfonyl)-5-substituted-2-thiohydantoins 2a-e. These compounds were oxidized with HNO3 to yield 1-(p-toluenesulfonyl)-5-substituted hydantoins 3a-e. The enantiomeric ratios of 3a-e were determined by 1H NMR spectroscopy using Eu(hfc)3. The antidiabetic activity of 3a-d has been determined.

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4

Chowdhry, Mubarik M., D. Michael P. Mingos, Andrew J. P. White, and David J. Williams. "Syntheses and characterization of 5-substituted hydantoins and thiazolines—implications for crystal engineering of hydrogen bonded assemblies. Crystal structures † of 5-(2-pyridylmethylene)hydantoin, 5-(2-pyridylmethylene)-2-thiohydantoin, 5-(2-pyridylmethylene)thiazolidine-2,4-dione, 5-(2-pyridylmethylene)rhodanine and 5-(2-pyridylmethylene)pseudothiohydantoin †." Journal of the Chemical Society, Perkin Transactions 1, no. 20 (2000): 3495–504. http://dx.doi.org/10.1039/b004312p.

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5

Chowdhry, Mubarik, D. Michael P. Mingos, Andrew J. P. White, and David J. Williams. "ChemInform Abstract: Syntheses and Characterization of 5-Substituted Hydantoins and Thiazolines - Implications for Crystal Engineering of Hydrogen Bonded Assemblies. Crystal Structures of 5-(2-Pyridylmethylene)-hydantoin, 5-(2-Pyridylmethylene)-2-thiohyda." ChemInform 32, no. 9 (2001): no. http://dx.doi.org/10.1002/chin.200109017.

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6

Kaválek, Jaromír, Vladimír Macháček, Gabriela Svobodová, and Vojeslav Štěrba. "Base catalyzed cyclization of substituted esters of hydantoic and thiohydantoic acids." Collection of Czechoslovak Chemical Communications 51, no. 2 (1986): 375–90. http://dx.doi.org/10.1135/cccc19860375.

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Base catalyzed cyclization rates have been measured of 22 derivatives of hydantoic and thiohydantoic acid esters in water and methanol. The cyclization of methyl and ethyl esters of hydantoic and 5-methylhydantoic acids is accompanied by hydrolysis of the ester group, whereas with the other derivatives the hydrolysis does not take place. Hydrolysis of the cyclization products (hydantoin and thiohydantoin derivatives) is not significant under the kinetic conditions. The cyclization of methyl ester of 5-phenylhydantoic acid in methanol is reversible; the equilibrium mixture contains 30% of the s

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7

Bolla, Ratna Sekhar, Narasimha Murthy Gandikota та Ivaturi Venkata Kasi Viswanath. "Synthesis of Deuterium Labeled 5, 5-Dimethyl-3-(α, α, α-trifluoro-4-nitro-m-tolyl) Hydantoin". Current Radiopharmaceuticals 12, № 1 (2019): 82–87. http://dx.doi.org/10.2174/1874471012666181130162731.

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Objective: Stable and non-radioactive isotope labeled compounds gained significance in recent drug discovery and other various applications such as bio-analytical studies. The modern bioanalytical techniques can study the adverse therapeutic effects of drugs by comparing isotopically labeled internal standards. A well-designed labeled compound can provide high-quality information about the identity and quantification of drug-related compounds in biological samples. This information can be very useful at key decision points in drug development. In this study, we tried to synthesize Nilutamide-

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8

Macháček, Vladimír, Gabriela Svobodová, and Vojeslav Štěrba. "Kinetics and mechanism of base-catalyzed cyclization of substituted amides and nitriles of hydantoic acid." Collection of Czechoslovak Chemical Communications 52, no. 1 (1987): 140–55. http://dx.doi.org/10.1135/cccc19870140.

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Rates of base-catalyzed cyclizations of 8 substituted derivatives of hydantoic acid amide type R3-NH(5)-CO(4)-NR2(3)-CH2(2)-CO(1)-NHR1 and 9 nitriles type R3-NH(5)-CO(4)-NR2(3)-CHR1(2)-CN have been measured in aqueous and methanolic media. The cyclization of the amides in aqueous medium is also accompanied by hydrolysis of the hydantoins formed. In some cases the hydrolysis rate constant is greater than the corresponding cyclization reaction rate constant. With the least reactive amides, the cyclization is also accompanied by hydrolysis of the amide group. The rate of the cyclization reactions

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9

Theodore, Cynthia E., S. Naveen, S. B. Benaka Prasad, M. Madaiah, C. S. Ananda Kumar, and N. K. Lokanath. "Crystal structure of 1′-(2-methylpropyl)-2,3-dihydrospiro[1-benzothiopyran-4,4′-imidazolidine]-2′,5′-dione." Acta Crystallographica Section E Structure Reports Online 70, no. 9 (2014): o1043—o1044. http://dx.doi.org/10.1107/s1600536814018030.

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In the title compound, C15H18N2O2S, the 2,3-dihydro-1-benzothiopyran ring adopts a sofa conformation and the hydantoin ring is twisted with respect to the benzene ring at 78.73 (17)°. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into inversion dimers.

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10

Kieć-Kononowicz, K., and E. Szymańska. "Antimycobacterial activity of 5-arylidene derivatives of hydantoin." Il Farmaco 57, no. 11 (2002): 909–16. http://dx.doi.org/10.1016/s0014-827x(02)01292-2.

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11

El-Barbary, Ahmed A., Ahmed I. Khodair, Erik B. Pedersen, and Claus Nielsen. "Synthesis of 3′-Amino and 5′-Amino Hydantoin 2′-Deoxynucleosides." Nucleosides and Nucleotides 13, no. 1-3 (1994): 707–17. http://dx.doi.org/10.1080/15257779408013274.

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12

Lotfy Aly, Youssef. "5-Pyrenylidene-hydantoin, 2-thiohydantoin derivatives: synthesis,S- andN-alkylation." Journal of Sulfur Chemistry 28, no. 4 (2007): 371–82. http://dx.doi.org/10.1080/17415990701385945.

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13

LU, J., M. AN, and H. ZHENG. "Effect of 2-butyne-1, 4-diol on silver electrodeposition from 5, 5-dimethyl hydantoin solutions." Rare Metals 25, no. 6 (2006): 255–59. http://dx.doi.org/10.1016/s1001-0521(08)60093-5.

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14

Szymańska, Ewa, Katarzyna Kieć-Kononowicz, Anna Białecka, and Andrzej Kasprowicz. "Antimicrobial activity of 5-arylidene aromatic derivatives of hydantoin. Part 2." Il Farmaco 57, no. 1 (2002): 39–44. http://dx.doi.org/10.1016/s0014-827x(01)01172-7.

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15

CHACÓN, C., J. A. HENAO, J. JAMALIS, P. RIVAS, W. VELÁSQUEZ, and G. E. DELGADO. "SYNTHESIS, CRYSTAL STRUCTURE AND HIRSHFELD SURFACE ANALYSIS OF 1-ACETYL-5-(2-METHYLPROPYL)-2-THIOXO-IMIDAZOLIDIN- 4-ONE." Periódico Tchê Química 15, no. 29 (2018): 292–99. http://dx.doi.org/10.52571/ptq.v15.n29.2018.292_periodico29_pgs_292_299.pdf.

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The hydantoin and thiohydantoin heterocycles are present in a wide range of biologically active compounds including therapeutic drugs for the treatment of seizures and anti-tumor compounds. Thiohydantoins, have also been used as anti-convulsant agents and are present in fungicides, herbicides and natural products. However, the principal current interest comes from the application of thiohydantoins for the treatment of prostate cancers. Structural characterization of hydantoin and thiohydantoin are important to comprehend their effect mechanisms because of their considerable biological effects.

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16

Niopas, Ioannis, and Gordon A. Smail. "N-substituted tricyclic isoquinoline hydantoins." Collection of Czechoslovak Chemical Communications 55, no. 2 (1990): 540–45. http://dx.doi.org/10.1135/cccc19900540.

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Mannich condensation of the 1,3-dioxo-5H-10,10a-dihydroimidazo[1,5-b]isoquinoline (Ia) and 5-ethoxy-10-bromo-1,3-dioxo-5H-imidazo[1,5-b]isoquinoline (IVa) with secondary amines gave a series of N-2-aminomethyl isoquinoline hydantoins IIa-IIg and IVb, respectively. Alkylation of Ia with N,N-dialkylaminoethyl chlorides and ethyl chloroacetate afforded the N-dialkylaminoethyl and N-ethoxycarbonylmethyl derivatives Va, Vb and IIh. The N-2-hydroxymethyl and N-2-amino isoquinoline hydantoins IIj and If were also prepared.

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17

Dios, Alfonso de, Maria Luz de la Puente, Alfonso Rivera-Sagredo, and Juan Felix Espinosa. "Structural and conformational studies of 5-(1H-pyrrol-2-ylmethylene)-substituted imidazolidine-2,4-diones and thiazolidine-2,4-diones." Canadian Journal of Chemistry 80, no. 10 (2002): 1302–7. http://dx.doi.org/10.1139/v02-175.

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Some imidazolidine-2,4-dione (hydantoin) and thiazolidine-2,4-dione (TZD) derivatives with a 1H-pyrrol-2-ylmethylene substituent at the 5-position (18) have been synthesized via an aldol condensation reaction. A mixture of Z- and E- stereoisomers was obtained, as confirmed by HPLC and NMR studies. Assignment of the stereochemistry was achieved through chemical shift knowledge, NOE, and 3JH,C data. The conformation of the molecules depends on the configuration at the double bond. While the (NH,C cis) form is the most stable conformer for the E-isomer, the (NH,C trans) form is the preferred con

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18

Todorov, Petar, Rosica Petrova, Emilia Naydenova, and Boris Shivachev. "Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins." Open Chemistry 7, no. 1 (2009): 14–19. http://dx.doi.org/10.2478/s11532-008-0087-3.

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AbstractThe crystal structures of 3-amino-cycloheptanespiro-4′-imidazolidine-2′,5′-dione (I) {systematic name: 3-amino-1,3-diazaspiro[4.6] undecane-2,4-dione} and 3-amino-cyclooctanespiro-4′-imidazolidine-2′,5′-dione (II) {systematic name: 3-amino-1,3-diazaspiro[4.7] dodecane-2,4-dione}, have been determined. In both compounds the polar hydantoin groups cause molecules to aggregate via N-H...O and N-H...N interactions, forming a layer structure, in which the cycloalkane rings project outwards from the central, more polar, region. The observed molecular structure is compared with that calculate

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19

Lee, Dong-Cheol, Seung-Goo Lee, and Hak-Sung Kim. "Production of d-p-hydroxyphenylglycine from d,l-5-(4-hydroxyphenyl)hydantoin using immobilized thermostable d-hydantoinase from Bacillus stearothermophilus SD-1." Enzyme and Microbial Technology 18, no. 1 (1996): 35–40. http://dx.doi.org/10.1016/0141-0229(96)00062-2.

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20

Jakšea, Renata, Vesna Krošelj, Simon Rečnik, et al. "Stereoselective Synthesis of 5-[(Z)-Heteroarylmethylidene] Substituted Hydantoins and Thiohydantoins as Aplysinopsin Analogs." Zeitschrift für Naturforschung B 57, no. 4 (2002): 453–59. http://dx.doi.org/10.1515/znb-2002-0411.

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3-Substituted 5-[(Z)-heteroarylmethylidene]imidazolidine-2,4-dione and 5-[(Z)-heteroarylmethylidene]- 2-thiooxoimidazolidin-4-one derivatives were prepared stereoselectively by coupling of 5-(dimethylamino)methylidene substituted hydantoin and thiohydantoin derivatives with carbocyclic and heterocyclic C-nucleophiles.Configuration around the exocyclic C=C double bond was determined by NMR, using NOESY and 2D HMBC techniques.

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21

Marton, Janos, Janos Enisz, Sandor Hosztafi, and Tibor Timar. "Preparation and fungicidal activity of 5-substituted hydantoins and their 2-thio analogs." Journal of Agricultural and Food Chemistry 41, no. 1 (1993): 148–52. http://dx.doi.org/10.1021/jf00025a031.

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22

Obradović, Ana, Miloš Matić, Branka Ognjanović, et al. "Anti-Tumor Mechanisms of Novel 3-(4-Substituted Benzyl)-5-Isopropil-5- Phenylhydantoin Derivatives in Human Colon Cancer Cell Line." Anti-Cancer Agents in Medicinal Chemistry 19, no. 12 (2019): 1491–502. http://dx.doi.org/10.2174/1871520619666190425180610.

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Background: Hydantoin and its newly synthesized derivatives have recently become a focus of interest due to their numerous biological activities and newly emerging beneficial effects in different pathological conditions, including cancer. Objective: The aim of this study was to evaluate the possible anti-tumor mechanisms of a series of newly synthesized 3-(4-substituted benzyl)-5-isopropyl-5-phenylhydantoin derivatives in different aspects of cell physiology of human colon cancer cell line, HCT-116. Methods: The increasing concentrations of derivatives (0.01µM up to 100µM) were applied to cell

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23

Aly, Youssef L., Ashraf A. El-Shehawy, Adel M. Attia, and Mohmed E. Sobh. "5-Anthracenylidene and 5-(4-Benzyloxy-3-methoxy)benzylidene-hydantoin and 2-Thiohydantoin Derivatives, Synthesis, and S-Alkylation." Phosphorus, Sulfur, and Silicon and the Related Elements 186, no. 7 (2011): 1572–84. http://dx.doi.org/10.1080/10426507.2010.525977.

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24

DZIEDZIC, B., M. J. KOROHODA, and E. RYDZIK. "ChemInform Abstract: Synthesis of 3-Aryl(alkyl)-5-(1′,2′,3′,4′-butanetetraol)-hydantoins." ChemInform 26, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199523203.

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25

Gerhardt, Valeska, Maya Tutughamiarso, and Michael Bolte. "Conformational studies of hydantoin-5-acetic acid and orotic acid." Acta Crystallographica Section C Crystal Structure Communications 68, no. 2 (2012): o92—o98. http://dx.doi.org/10.1107/s0108270112001151.

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Hydantoin-5-acetic acid [2-(2,5-dioxoimidazolidin-4-yl)acetic acid] and orotic acid (2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid) each contain one rigid acceptor–donor–acceptor hydrogen-bonding site and a flexible side chain, which can adopt different conformations. Since both compounds may be used as coformers for supramolecular complexes, they have been crystallized in order to examine their conformational preferences, giving solvent-free hydantoin-5-acetic acid, C5H6N2O4, (I), and three crystals containing orotic acid, namely, orotic acid dimethyl sulfoxide monosolvate, C5H4N2O

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26

Kurczab, Rafał, Wesam Ali, Dorota Łażewska, et al. "Computer-Aided Studies for Novel Arylhydantoin 1,3,5-Triazine Derivatives as 5-HT6 Serotonin Receptor Ligands with Antidepressive-Like, Anxiolytic and Antiobesity Action In Vivo." Molecules 23, no. 10 (2018): 2529. http://dx.doi.org/10.3390/molecules23102529.

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This study focuses on the design, synthesis, biological evaluation, and computer-aided structure-activity relationship (SAR) analysis for a novel group of aromatic triazine-methylpiperazines, with an hydantoin spacer between 1,3,5-traizine and the aromatic fragment. New compounds were synthesized and their affinities for serotonin 5-HT6, 5-HT1A, 5-HT2A, 5-HT7, and dopamine D2 receptors were evaluated. The induced-fit docking (IFD) procedure was performed to explore the 5-HT6 receptor conformation space employing two lead structures. It resulted in a consistent binding mode with the activity da

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27

Benaka Prasad, S. B., S. Naveen, M. Madaiah, N. K. Lokanath, Ismail Warad, and Muneer Abdoh. "Crystal structure of 1′-ethylspiro[chroman-4,4′-imidazolidine]-2′,5′-dione: a hydantoine derivative." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (2015): o705—o706. http://dx.doi.org/10.1107/s2056989015016175.

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The title compound, C13H13N2O3, a hydantoin derivative, crystallized with two molecules (AandB) in an asymmetric unit. In moleculeA, the imidazolidine ring is twisted about the C—N bond involving the spiro C atom, while in moleculeBthis ring is flat (r.m.s. deviation = 0.010 Å). The pyran rings in both molecules have distorted half-chair conformations. The mean plane of the imidazolidine ring is inclined to the aromatic ring of the chroman unit by 79.71 (11)° in moleculeAand 82.83 (12)° in moleculeB. In the crystal, pairs of N—H...O hydrogen bonds link the individual molecules to formA–AandB–B

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28

Ibrahim, Sabrin R. M., Gamal A. Mohamed, Lamiaa A. Shaala, and Diaa T. A. Youssef. "Non-Alkaloidal Compounds from the Bulbs of the Egyptian Plant Pancratium maritimum." Zeitschrift für Naturforschung C 69, no. 3-4 (2014): 92–98. http://dx.doi.org/10.5560/znc.2013-0111.

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Phytochemical investigation of the cytotoxic fractions of fresh bulbs of Pancratium maritimum L. led to the isolation and structure identification of two new compounds, pancricin (1) and pancrichromone (4), together with four known compounds, including 2,4-dihydroxy-6- methoxy-3-methyl acetophenone (2), 5-formylfurfuryl acetate (3), 7-β-D-glucosyloxy-5-hydroxy-2- methylchromone (5), and ethyl-b-D-glucopyranoside (6). Their structures were established on the basis of 1D and 2D NMR spectroscopy (1H, 13C, COSY, HSQC, and HMBC), as well as HR mass spectral analyses. The compounds were evaluated fo

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29

Bakalova, Adriana G., Rossen T. Buyukliev, Rositsa P. Nikolova, Boris L. Shivachev, Rositsa A. Mihaylova, and Spiro M. Konstantinov. "Synthesis, Spectroscopic Properties, Crystal Structure And Biological Evaluation of New Platinum Complexes with 5-methyl-5-(2-thiomethyl)ethyl Hydantoin." Anti-Cancer Agents in Medicinal Chemistry 19, no. 10 (2019): 1243–52. http://dx.doi.org/10.2174/1871520619666190214103345.

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Background: The accidental discovery of Cisplatin’s growth-inhibiting properties a few decades ago led to the resurgence of interest in metal-based chemotherapeutics. A number of well-discussed factors such as severe systemic toxicity and unfavourable physicochemical properties further limit the clinical application of the platinating agents. Great efforts have been undertaken in the development of alternative platinum derivatives with an extended antitumor spectrum and amended toxicity profile as compared to the reference drug cisplatin. The rational design of conventional platinum analogues

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Rivière, Johann, François Bergeron, Sébastien Tremblay, Didier Gasparutto, Jean Cadet, and J. Richard Wagner. "Oxidation of 5-Hydroxy-2‘-deoxyuridine into Isodialuric Acid, Dialuric Acid, and Hydantoin Products." Journal of the American Chemical Society 126, no. 21 (2004): 6548–49. http://dx.doi.org/10.1021/ja049438f.

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31

Łażewska, Dorota, Piotr Maludziński, Ewa Szymańska, and Katarzyna Kieć-Kononowicz. "The lipophilicity estimation of 5-arylidene derivatives of (2-thio)hydantoin with antimycobacterial activity." Biomedical Chromatography 21, no. 3 (2007): 291–98. http://dx.doi.org/10.1002/bmc.755.

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32

Aly, Youssef Lotfy. "5-Chromonylidene-hydantoins, 2-Thiohydantoins, Synthesis and Reaction with Some Alkylhalides, Some Amines and Some Diazoalkanes." Phosphorus, Sulfur, and Silicon and the Related Elements 180, no. 1 (2005): 1–18. http://dx.doi.org/10.1080/10426500490494769.

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Drev, Miha, Uroš Grošelj та Jurij Svete. "Transformations of β-aryl-N-Cbz-α,β-didehydro-α-amino esters with hydrazine hydrate". Zeitschrift für Naturforschung B 71, № 6 (2016): 623–31. http://dx.doi.org/10.1515/znb-2015-0221.

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AbstractCyclizations of Cbz-protected α,β-didehydro-β-arylalanine esters 1 with excess hydrazine hydrate afforded mixtures of the expected 3-pyrazolidinones 2 and the unexpected 1-amino-5-benzylidenehydantoins 6 and N-Cbz-β-arylalanine hydrazides 7. Presumably, the pyrazolidinones 2 and hydantoins 6 are formed as primary products via competitive 1,2- and 1,4-addition of hydrazine hydrate followed by cyclization, whereas β-arylalanine hydrazides 7 are formed as secondary products via reductive cleavage of the C(5)–N(1) bond in pyrazolidinones 2. The overall selectivity depends on the reaction t

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34

Kushev, Daniel, Galina Gorneva, Venelin Enchev, et al. "Synthesis, cytotoxicity, antibacterial and antitumor activity of platinum(II) complexes of 3-aminocyclohexanespiro-5-hydantoin." Journal of Inorganic Biochemistry 89, no. 3-4 (2002): 203–11. http://dx.doi.org/10.1016/s0162-0134(01)00420-2.

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35

Filliatre, Claude, and Et Christian Servens. "Réaction de l'acide chromone-2 carboxylique avec les carbodiimides: Synthèse de spiro [(chromanone-4)-2: 5′-hydantoïnes]." Journal of Heterocyclic Chemistry 22, no. 4 (1985): 1009–10. http://dx.doi.org/10.1002/jhet.5570220415.

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36

Himbert, Gerhard, and Oliver Gerulat. "Einige Umsetzungen von Inhydrazinen mit Isocyanaten: [2+2]- und [4+2]Cycloadditionen, (Hydrazinoethinyl)metallierung / Some Reactions of Ynehydrazines with Isocyanates: [2+2]- and [4+2]Cycloadditions, (Hydrazinoethynyl)metallation." Zeitschrift für Naturforschung B 56, no. 11 (2001): 1196–204. http://dx.doi.org/10.1515/znb-2001-1115.

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The (silylethynyl)- and the (tolylethinyl)-hydrazines 1a and 1b react with aryl isocyanates 2a-e and arylsulfonyl isocyanates 2f,g to form the corresponding substituted 3-arylimino-(or arylsulfonylimino-) 1,1,2-trimethyl-5-oxopyrazolidinium-4-ides 3a-h. The silyl group in the 4-position can be replaced by a hydrogen atom (formation of 6a-e). Heating of 6d in toluene induced the unequivocal transformation of the betaine to an isomer, the spectrocopic data of which are in concordance with those of the 4-quinolone derivative 7. Aroyl isocyanates 8 react in a [4+2]cycloaddition with la to furnish

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37

Ghanbari, Mohammad M., Marzieh Jamali, Gyula Batta, and Attila C. Bényei. "Synthesis and dynamic NMR studies of novel hydantoin and thiohydantoin derivatives. Crystal structure of diethyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl) fumarate and diethyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1H-imidazol-1-yl)fumarate." Journal of Chemical Research 41, no. 5 (2017): 309–13. http://dx.doi.org/10.3184/174751917x14932244903881.

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The reaction of stoichiometric amounts of dialkyl acetylenedicarboxylates with triphenylphosphine in the presence of hydantoins or thiohydantoins afforded stable crystalline phosphorus ylides. These compounds undergo smooth elimination of PPh3 to produce dialkyl 2-(4,4-diaryl-2,5-dioxoimidazolidin-1-yl)fumarate, 4 or dialkyl 2-(4,4-diaryl-2-mercapto-5-oxo-4,5-dihydro-1 H-imidazol-1-yl)fumarate, 7. Single crystal X-ray diffraction study on 4b and 7b proved the structures unambiguously with C=O and SH functionality at the 2-position of the imidazole ring, respectively. Dynamic effects were obser

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Koch, Daniela, Karlheinz Sünkel, and Wolfgang Beck. "Metallkomplexe mit biologisch wichtigen Liganden, CXI. Phosphan-Gold(I), -Nickel(II) und -Platin(II) Komplexe mit dem Anion von Hydantoin und 3,4-Pyridindicarbonsäureimid/Metal Complexes of Biologically Important Ligands, CXI. Phosphine Gold(I), Nickel(II) and Platinum(II) Complexes with the Anion of Hydantoin and of 3,4 Pyridine Dicarboxylic Imide." Zeitschrift für Naturforschung B 54, no. 1 (1999): 96–102. http://dx.doi.org/10.1515/znb-1999-0118.

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The anions of hydantoin (L1) and of the imide of 3,4-pyridine dicarboxylic acid (L2) form the complexes Ph3PAu(L1-H+) (1), Ph3PAu(L2-H+) (2), (nBu3P)2Ni(L1-H+)2 (3) and the ligand bridged compounds Ph3PAu(L2-H+)M(PEt3)Cl2 (M = Pd, Pt, 4, 5). With the neutral ligand L2 the complexes Cp*Ir(Cl)2(L2) (6), (ρ-cymene)Ru(Cl)2 (L2) (7) and (Et3P)(Cl)2Pd(L2) (8) were obtained. Complexes 1, 2 and 6 were characterized by X-ray diffraction.

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39

AlTarabeen, Mousa, Amal Hassan Aly, Catalina Francis Perez Hemphill, Mohammed Rasheed, Victor Wray, and Peter Proksch. "New nitrogenous compounds from a Red Sea sponge from the Gulf of Aqaba." Zeitschrift für Naturforschung C 70, no. 3-4 (2015): 75–78. http://dx.doi.org/10.1515/znc-2014-4197.

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Abstract Chemical investigation of an unknown marine sponge, which was collected in the Gulf of Aqaba (Jordan), afforded a new brominated alkaloid 3-amino-1-(2-amino-4-bromophenyl)propan-1-one (1), as well as 7-bromoquinolin-4(1H)-one (2) which had previously only been reported as a synthetic compound. In addition, caulerpin (6), previously only known to be produced by algae, was likewise isolated. Furthermore, three known alkaloids including (Z)-5-(4-hydroxybenzylidene)-hydantoin, (Z)-6-bromo-3′-deimino-2′,4′-bis(demethyl)-3′-oxoaplysinopsin, and 6-bromoindole-3-carbaldehyde (3–5), were also

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40

Mathur, Pradeep, Raj Kumar Joshi, Dhirendra Kumar Rai, Badrinath Jha, and Shaikh M. Mobin. "One pot synthesis of maleimide and hydantoin by Fe(CO)5 catalyzed [2 + 2 + 1] co-cyclization of acetylene, isocyanate and CO." Dalton Transactions 41, no. 16 (2012): 5045. http://dx.doi.org/10.1039/c2dt11942k.

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41

Goyal, Rajendra N., and Neeraj Kumar. "Cyclic Voltammetry and Chronoamperometry of 1-Methylxanthine: Evidence for an Unstable para-Quinonoid Diimine Intermediate." Australian Journal of Chemistry 52, no. 1 (1999): 43. http://dx.doi.org/10.1071/c98095.

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The electrooxidation of the adenosine antagonist 1-methylxanthine has been studied in the pH range 2·5–10·7 at the pyrolytic graphite electrode. The initial 4e, 4H+ oxidation step leads to the formation of an unstable diimine, for which the half-life was found to be 1·8 s by chronoamperometry. The diimine is readily attacked by water to give a carbinolamine which decomposes in a pseudo first-order reaction to give, as the major products, 1-methylalloxan at pH 3·0 and 5-hydroxy-5-(methylcarbamoyl)hydantoin at pH 7·0. The oxidation products were identified. The diimine can also be reversibly red

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42

Yokomatsu, Tsutomu, Nobuko Nakabayashi, Keita Matsumoto, and Shiroshi Shibuya. "Lipase-catalyzed kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane. Application to enantioselective synthesis of 1-diethylphosphonomethyl-2-(5′-hydantoinyl)cyclohexane." Tetrahedron: Asymmetry 6, no. 12 (1995): 3055–62. http://dx.doi.org/10.1016/0957-4166(95)00403-3.

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43

Chowdhry, Mubarik M., Andrew D. Burrows, D. Michael P. Mingos, Andrew J. P. White, and David J. Williams. "Synthesis and crystal structure of 5-(2-pyridylmethylene)hydantoin (Hpyhy) and complexes of pyhy with nickel(II) and copper(II)." Journal of the Chemical Society, Chemical Communications, no. 15 (1995): 1521. http://dx.doi.org/10.1039/c39950001521.

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44

Kussler, M. "Über die reaktion von enaminoketonen mit phenylisocyanat: 1,2-dihydropyridin-2-spiro-hydantoine, farbstoffe mit starker festkörperfluoreszenz." Dyes and Pigments 8, no. 3 (1987): 179–87. http://dx.doi.org/10.1016/0143-7208(87)80002-5.

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45

Wermuth, Urs D., Ian D. Jenkins, Raymond C. Bott, Karl A. Byriel, and Graham Smith. "Some Stereochemical Aspects of the Strecker Synthesis and the Bucherer - Bergs Reaction." Australian Journal of Chemistry 57, no. 5 (2004): 461. http://dx.doi.org/10.1071/ch03202.

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Both the Strecker and Bucherer–Bergs reactions convert the norbornane keto ester methyl bicyclo[2.2.1]hept-6-one-2-endo-carboxylate into the lactam 6-endo-aminobicyclo[2.2.1]heptane-2-endo-carboxylic acid-γ-lactam-6-exo-carboxylic acid. This lactam is unusually stable and cannot be hydrolyzed to the corresponding amino acid. The stereochemistry in the Strecker reaction, in which the amino group is endo, is contrary to that expected from literature precedent. The stereochemistry in the Bucherer–Bergs reaction, in which the amino group is also endo, has been confirmed by X-ray crystallographic a

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Wilms, B., A. Wiese, C. Syldatk, M. Siemann-Herzberg, R. Mattes, and J. Altenbuchner. "Development of anEscherichia coli Whole Cell Biocatalyst for the Production of L-Amino Acids from D,L-5-Monosubstituted Hydantoins." Chemie Ingenieur Technik 74, no. 5 (2002): 657. http://dx.doi.org/10.1002/1522-2640(200205)74:5<657::aid-cite657>3.0.co;2-k.

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47

Lubelska, Annamaria, Gniewomir Latacz, Magdalena Jastrzębska-Więsek, et al. "Are the Hydantoin-1,3,5-triazine 5-HT6R Ligands a Hope to a Find New Procognitive and Anti-Obesity Drug? Considerations Based on Primary In Vivo Assays and ADME-Tox Profile In Vitro." Molecules 24, no. 24 (2019): 4472. http://dx.doi.org/10.3390/molecules24244472.

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Though the 5-HT6 serotonin receptor is an important target giving both agonists and antagonists similar therapeutic potency in the treatment of topic CNS-diseases, no 5-HT6R ligand has reached the pharmaceutical market yet due to the too narrow chemical space of the known 5-HT6R agents and insufficient “drugability.” Recently, a new group of non-indole and non-sulfone hydantoin-triazine 5-HT6R ligands was found, where 3-((4-amino-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-yl)methyl)-5-methyl-5-(naphthalen-2-yl)imidazolidine-2,4-dione (KMP-10) was the most active member. This study is focused o

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48

YOKOMATSU, T., N. NAKABAYASHI, K. MATSUMOTO, and S. SHIBUYA. "ChemInform Abstract: Lipase-Catalyzed Kinetic Resolution of cis-1-Diethylphosphonomethyl-2- hydroxymethylcyclohexane. Application to Enantioselective Synthesis of 1-Diethylphosphonomethyl-2-(5′-hydantoinyl)cyclohexane." ChemInform 27, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199617031.

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Popiół, Justyna, Agnieszka Gunia-Krzyżak, Kamil Piska, et al. "Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group." Molecules 24, no. 12 (2019): 2321. http://dx.doi.org/10.3390/molecules24122321.

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Effective protection from the harmful effects of UV radiation may be achieved by using sunscreens containing organic or inorganic UV filters. The number of currently available UV filters is limited and some of the allowed molecules possess limitations such as systemic absorption, endocrine disruption properties, contact and photocontact allergy induction, and low photostability. In the search for new organic UV filters we designed and synthesized a series consisting of 5-benzylidene and 5-(3-phenylprop-2-en-1-ylidene)imidazolidine-2,4-dione (hydantoin) derivatives. The photoprotective activity

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50

Werner, S., D. M. Turner, P. G. Chambers, and K. M. Brummond. "Skeletal and appendage diversity as design elements in the synthesis of a discovery library of nonaromatic polycyclic 5-iminooxazolidin-2-ones, hydantoins, and acylureas." Tetrahedron 64, no. 29 (2008): 6997–7007. http://dx.doi.org/10.1016/j.tet.2008.02.033.

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