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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 (January 12, 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-carbamoylase gene was cloned closest to the promoter in order to obtain the highest level of synthesis of the enzyme, thus avoiding intermediate accumulation, which decreases the reaction rate. Both systems were able to produce 100% conversion and 100% optically pure d-methionine, d-leucine, d-norleucine, d-norvaline, d-aminobutyric acid, d-valine, d-phenylalanine, d-tyrosine, and d-tryptophan from the corresponding hydantoin racemic mixture. For the production of almost all d-amino acids studied in this work, system 1 hydrolyzed the 5-monosubstituted hydantoins faster than system 2.

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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 (December 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 (February 1, 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 (February 27, 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 starting ester. In all the cases the cyclization is subject to specific base catalysis; exceptions are esters of 5-phenylthiohydantoic and 5-phenyl-2-methylthiohydantoic acids whose cyclizations are subject to general base catalysis. Substituents always accelerate the cyclization. The 3-substituents have the greatest effects, the cyclization rate being considerably increased with bulk of the substituents; similarly large effect of 5-phenyl group consists mainly in its polar effects on the pre-equilibrium. The cyclization are slower in methanol at the same concentration of the lyate ion: the greatest difference (up to 3 orders of magnitude) is observed with the 5-phenyl derivatives.

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7

Bolla, Ratna Sekhar, Narasimha Murthy Gandikota, and Ivaturi Venkata Kasi Viswanath. "Synthesis of Deuterium Labeled 5, 5-Dimethyl-3-(α, α, α-trifluoro-4-nitro-m-tolyl) Hydantoin." Current Radiopharmaceuticals 12, no. 1 (March 4, 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- d6 which can be useful to study the adverse effects of Nilutamide, and based on these can modify or widen the new drug derivatives. Nilutamide is a nonsteroidal antiandrogen which is used in the treatment of prostate cancer. The aim of this study was to develop a synthetic approach to prepare deuterium labeled [2H6]-5, 5-dimethylimidazolidine-2, 4-dione and [2H6]-nilutamide. Methods: Since nilutamide is a derivative of hydantoin, it involves the synthesis of Dimethylhydantoin via Bucherer-Bergs hydantoin synthesis, followed by oxidative N-arylation with 4-iodo-1-nitro-2- (trifluoromethyl) benzene. Conclusion: We successfully synthesized [2H6]-nilutamide and [2H6]-dimethylhydantoin with good isotopic purity, measured to be of adequate quality for use as internal standards in bio-analytical studies. A brief mechanistic study of Bucherer-Bergs hydantoin reaction was carried and the reason for possible H/D exchange was explained.

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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 in water is higher than that in methanol (at the same concentration of the lyate ions) by the factor of 10-100. Substitution of hydrogen at 3 and 5 positions by methyl or phenyl groups causes an acceleration of the cyclization reaction, whereas a substitution in the amide group causes a considerable retardation. The greatest acceleration of the cyclization (by as much as 4 orders) is caused by introduction of phenyl group to the N(5) position, which is due to a substantial increase of concentration of the reactive anion.

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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 (August 23, 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 (November 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 (March 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 (August 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 (December 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 (January 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 (January 20, 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. In this work a thiohydantoin derivative, 1-acetyl-5-(2-methylpropyl)-2-thioxo-imidazolidin-4-one (I), has been obtained by the reaction of 2-amino-4-methylpentanoic acid with KSCN in acetic anhydride-acetic acid mixture. The heterocyclic compound was characterized by FTIR, NMR, powder and single-crystal X-ray diffraction analysis. This compound crystallizes in the triclinic system, space group P-1 (Nº2), Z=4, with two independent molecules in the unit asymmetric. The thiohydantoin (I) forms one-dimensional hydrogen bonded chains, via a single hydrogen bond between the carbonyl oxygens and the amine ring N3 position, that run along [100] direction, with graphset motif C(6). The nature of intermolecular interactions has been analyzed through Hirshfeld surfaces and 2D fingerprint plots.

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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 (October 1, 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 conformer for the Z-isomer. The temperature coefficients of the NH pyrrole protons reveal the existence of an intramolecular hydrogen bond for the E-isomers.Key words: hydantoin, TZD, NMR spectroscopy, conformational analysis, temperature coefficient.

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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 (March 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 calculated by density functional theory methods.

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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 (January 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, Gorazd Soršak, Jurij Svete, Branko Stanovnik, and Simona Golič Grdadolnik. "Stereoselective Synthesis of 5-[(Z)-Heteroarylmethylidene] Substituted Hydantoins and Thiohydantoins as Aplysinopsin Analogs." Zeitschrift für Naturforschung B 57, no. 4 (April 1, 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 (January 1993): 148–52. http://dx.doi.org/10.1021/jf00025a031.

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22

Obradović, Ana, Miloš Matić, Branka Ognjanović, Nenad Vuković, Milena Vukić, Predrag Đurđević, Gordana Ušćumlić, Bojan Božić, and Biljana B. Nedeljković. "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 (December 2, 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 cells during 24h, 48h, and 72h after which the evaluation of proliferation, apoptosis, oxidative/anti-oxidative status, nitrite production, and migration/invasion potential of treated cells was performed. Results: All tested compounds expressed the dose- and time-dependent anti-proliferative and pro-apoptotic activities against HCT-116 cells. The investigated derivatives induced a decrease in levels of oxidative stress parameters and an increase in levels of nitrite production by treated cells suggesting their significant antioxidative effects. The cell migration index and expression level of tumor invasion-promoting metalloproteinase- 9 (MMP-9) gene were significantly decreased after treatment with the tested hydantoin derivatives implicating their inhibitory role in colon cancer cell motility and invasion processes. The mRNA level of cyclooxygenase-2 (COX-2) gene as a pro-inflammatory gene related to colorectal carcinogenesis was reduced compared to values in the non-treated control cells indicating the significant anti-inflammatory/anti-tumor effects of these compounds. Conclusion: The obtained results show the significant anti-tumor potential of tested derivatives, especially 3- benzyl-5-isopropyl-5-phenylhydantoin and 3-(4-chlorobenzyl)-5-isopropyl-5-phenylhydantoin, suggesting their potential usage in the development of more effective chemotherapies.

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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 (July 1, 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 (August 17, 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 (January 18, 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, C5H4N2O4·C2H6OS, (IIa), dimethylammonium orotate–orotic acid (1/1), C2H8N+·C5H3N2O4−·C5H4N2O4, (IIb), and dimethylammonium orotate–orotic acid (3/1), 3C2H8N+·3C5H3N2O4−·C5H4N2O4, (IIc). The crystal structure of (I) shows a three-dimensional network, with the acid function located perpendicular to the ring. Interestingly, the hydroxy O atom acts as an acceptor, even though the carbonyl O atom is not involved in any hydrogen bonds. However, in (IIa), (IIb) and (IIc), the acid functions are only slightly twisted out of the ring planes. All H atoms of the acidic functions are directed away from the rings and, with respect to the carbonyl O atoms, they show an antiperiplanar conformation in (I) and synperiplanar conformations in (IIa), (IIb) and (IIc). Furthermore, in (IIa), (IIb) and (IIc), different conformations of the acid O=C—C—N torsion angle are observed, leading to different hydrogen-bonding arrangements depending on their conformation and composition.

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26

Kurczab, Rafał, Wesam Ali, Dorota Łażewska, Magdalena Kotańska, Magdalena Jastrzębska-Więsek, Grzegorz Satała, Małgorzata Więcek, 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 (October 3, 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 data. For the most active compounds found in each modification line, anti-obesity and anti-depressive-like activity in vivo, as well as “druglikeness” in vitro, were examined. Two 2-naphthyl compounds (18 and 26) were identified as the most active 5-HT6R agents within each lead modification line, respectively. The 5-(2-naphthyl)hydantoin derivative 26, the most active one in the series (5-HT6R: Ki = 87 nM), displayed also significant selectivity towards competitive G-protein coupled receptors (6–197-fold). Docking studies indicated that the hydantoin ring is stabilized by hydrogen bonding, but due to its different orientation, the hydrogen bonds form with S5.44 and N6.55 or Q6.58 for 18 and 26, respectively. Compound 26 exerted anxiolytic-like and antidepressant-like activities. Importantly, it demonstrated anti-obesity properties in animals fed palatable feed, and did not show toxic effects in vitro.

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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 (September 12, 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–Binversion dimers. The dimers are linkedviaN—H...O and C—H...O hydrogen bonds, forming sheets lying parallel to thebcplane,viz.(011). Within the sheets, theAandBmolecules are linked by C—H...π interactions.

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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 (April 1, 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 for their antimigratory and antiproliferative activities against the highly metastatic human prostate cancer cell line (PC-3M). Compound 5 was the most active compound displaying good activity in the proliferation assay comparable to that of the positive control 4-hydroxyphenylmethylene hydantoin, while it displayed only weak antimigratory activity compared to the positive control 4-ethylmercaptophenylmethylene hydantoin.

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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 (October 24, 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 and the re-evaluation of the empirically derived “structure- activity” relationships allowed for the synthesis of platinum complexes with great diversity in structural characteristics, biochemical stability and antitumor properties. Methods: The new compounds have been studied by elemental analyses, IR, NMR and mass spectral analyses. The structures of the organic compound and one of the new mixed/ammine Pt(II) complexes were studied by X-ray diffraction analysis. The cytotoxic effects of the compounds were studied vs. the referent antineoplastic agent cisplatin against four human tumour cell lines using the standard MTT-dye reduction assay for cell viability. The most promising complex 3 was investigated for acute toxicity in male and female H-albino-mice models. Results: A new organic compound (5-methyl-5-(2-thiomethyl)ethyl hydantoin) L bearing both S- and Ncoordinating sites and three novel platinum complexes, 1, 2 and 3 were synthesized and studied. Spectral and structural characterization concluded monodentate S-driven coordination of the ligand L to the metal center in complexes 1 and 2, whereas the same was acted as a bidentate N,S-chelator in complex 3. Ligand L crystallizes in the tetragonal space group I41/a (No 88) with one molecule per asymmetric unit. While complex 3 crystallizes in the monoclinic space group P21/c (No 14) with one molecule per asymmetric unit. In the same complex 3, the platinum ion coordinates an L ligand, a chloride ion and an ammonia molecule. In the in vitro experiments, the tested L and complexes 1 and 2 exhibited negligible cytotoxic activity in all tumor models. Accordingly, complex 3 is twice as potent as cisplatin in the HT-29 cells and is at least as active as cisplatin on the MDA-MB-231 breast cancer cell line. In the in vivo toxicity estimation of complex 3 no signs of common toxicity were observed. Conclusion: The Pt(II)-bidentate complex 3 exhibited significant cytotoxic potential equaling or surpassing that of the reference drug cisplatin in all the tested tumor models. Negligible anticancer activity on the screened tumor types has been shown by the ligand L and its Pt(II) and Pt(IV) complexes 1 and 2, respectively. Our study on the acute toxicity of the most active complex 3 proved it to be non-toxic in mice models.

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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 (June 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 (January 1, 2005): 1–18. http://dx.doi.org/10.1080/10426500490494769.

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33

Drev, Miha, Uroš Grošelj, and Jurij Svete. "Transformations of β-aryl-N-Cbz-α,β-didehydro-α-amino esters with hydrazine hydrate." Zeitschrift für Naturforschung B 71, no. 6 (June 1, 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 time and on the β-substituent in the starting dehydroalanine ester 1.

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34

Kushev, Daniel, Galina Gorneva, Venelin Enchev, Emilya Naydenova, Julita Popova, Svetoslav Taxirov, Liliana Maneva, Konstantin Grancharov, and Nadejda Spassovska. "Synthesis, cytotoxicity, antibacterial and antitumor activity of platinum(II) complexes of 3-aminocyclohexanespiro-5-hydantoin." Journal of Inorganic Biochemistry 89, no. 3-4 (April 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 (July 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 (November 1, 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 the 1,3-oxazin-4-ones 9a and b. The stannylated ynehydrazine 1c adds the cumulenic system of an aryl isocyanate (2d) across the Csp-Sn single bond, and trimethylstannyl .N-(p-chlorophenyl)-3-(trimethylhydrazino)propiolimidate 10 is isolated. With two molecules of 2d the hydantoin derivative 11 is formed.

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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 (May 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 observed in the NMR spectra of these compounds and were attributed to restricted rotation around the carbon-nitrogen single bonds. Rotational energy barrier (Δ G#) for their interconversion process of rotational isomers equals to (53.6 and 17.2) ± 2 kcal mol−1.

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38

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 (January 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 (March 1, 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 obtained. All compounds were unambiguously elucidated based on extensive 1D and 2D NMR spectroscopy, LCMS, as well as by comparison with the literature and tested for their cytotoxic activity toward the mouse lymphoma cell line L5178Y.

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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 reduced to the 2,6,8-trioxopurine anion derivative which is also formed by the 2e, 2H+ reduction of the carbinolamine. A tentative mechanism for the formation of the products has also been suggested.

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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 (December 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 (January 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 analysis of the intermediate spirohydantoin (±)-bicyclo[2.2.1]heptane-2-endo-carboxylic acid-6-spiro-5′-hydantoin.

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46

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 (May 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, Magdalena Kotańska, Rafał Kurczab, Anna Partyka, Małgorzata Anna Marć, 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 (December 6, 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 on wider pharmacological and “druglikeness” characteristics for KMP-10. A computer-aided insight into molecular interactions with 5-HT6R has been performed. “Druglikeness” was examined using an eight-test panel in vitro, i.e., a parallel artificial membrane permeability assay (PAMPA), and Caco-2 permeability-, P-glycoprotein (Pgp) affinity-, plasma protein binding-, metabolic stability- and drug–drug interaction-assays, as well as mutagenicity- and HepG2-hepatotoxicity risk tests. Behavioral studies in vivo, i.e., elevated plus-maze (EPM) and novel object recognition (NOR) tests, were performed. Extended studies on the influence of KMP-10 on rats’ metabolism, including biochemical tests, were conducted in vivo. Results indicated significant anxiolytic and precognitive properties, as well as some anti-obesity properties in vivo, and it was found to satisfy the “druglikeness” profile in vitro for KMP-10. The compound seems to be a good lead-structure and candidate for wider pharmacological studies in search for new CNS-drugs acting via 5-HT6R.

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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 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199617031.

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49

Popiół, Justyna, Agnieszka Gunia-Krzyżak, Kamil Piska, Dorota Żelaszczyk, Paulina Koczurkiewicz, Karolina Słoczyńska, Katarzyna Wójcik-Pszczoła, et al. "Discovery of Novel UV-Filters with Favorable Safety Profiles in the 5-Arylideneimidazolidine-2,4-dione Derivatives Group." Molecules 24, no. 12 (June 24, 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 of the tested compounds was confirmed in methanol solutions and macrogol formulations. The most promising compounds possessed similar UV protection parameter values as selected commercially available UV filters. The compound diethyl 2,2′-((Z)-4-((E)-3-(4-methoxyphenyl)allylidene)-2,5-dioxoimidazolidine-1,3-diyl)diacetate (4g) was characterized as an especially efficient UVA photoprotective agent with a UVA PF of 6.83 ± 0.05 and favorable photostability. Diethyl 2,2′-((Z)-4-(4-methoxybenzylidene)-2,5-dioxo- imidazolidine-1,3-diyl)diacetate (3b) was the most promising UVB-filter, with a SPFin vitro of 3.07 ± 0.04 and very good solubility and photostability. The main photodegradation products were geometric isomers of the parent compounds. These compounds were also shown to be non-cytotoxic at concentrations up to 50 µM when tested on three types of human skin cells and possess no estrogenic activity, according to the results of a MCF-7 breast cancer model.

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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 (July 2008): 6997–7007. http://dx.doi.org/10.1016/j.tet.2008.02.033.

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