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Volumn 5, Issue 1, 2011, Pages

Solvent effects on the structure-property relationship of anticonvulsant hydantoin derivatives: A solvatochromic analysis

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EID: 80053940110     PISSN: None     EISSN: 1752153X     Source Type: Journal    
DOI: 10.1186/1752-153X-5-62     Document Type: Article
Times cited : (20)

References (44)
  • 1
    • 0022497683 scopus 로고
    • Phenytoin: mechanisms of its anticonvulsant action
    • Yaari Y, Selzer ME, Pincus JH: Phenytoin: mechanisms of its anticonvulsant action. Ann Neurol. 1986, 20: 171-184. 10.1002/ana.410200202.
    • (1986) Ann Neurol , vol.20 , pp. 171-184
    • Yaari, Y.1    Selzer, M.E.2    Pincus, J.H.3
  • 2
    • 0018834572 scopus 로고
    • A major pathway of mephenytoin metabolism in man. Aromatic hydroxylation to p-hydroxymephenytoin
    • Küpfer A, Brilis GM, Watson JT, Harris TM: A major pathway of mephenytoin metabolism in man. Aromatic hydroxylation to p-hydroxymephenytoin. Drug Metab Dispos. 1980, 8: 1-4.
    • (1980) Drug Metab Dispos , vol.8 , pp. 1-4
    • Küpfer, A.1    Brilis, G.M.2    Watson, J.T.3    Harris, T.M.4
  • 3
    • 0009741239 scopus 로고
    • Reactions to nirvanol, phenytoin sodium and phenobarbital: report of a case of ectodermosis erosiva pluriorificialis following the ingestion of phenytoin sodium
    • Ellis FA: Reactions to nirvanol, phenytoin sodium and phenobarbital: report of a case of ectodermosis erosiva pluriorificialis following the ingestion of phenytoin sodium. South Med J. 1943, 36: 575-579. 10.1097/00007611-194308000-00007.
    • (1943) South Med J , vol.36 , pp. 575-579
    • Ellis, F.A.1
  • 4
    • 0021250891 scopus 로고
    • Ethotoin in seizures of childhood and adolescence
    • Carter CA, Helms RA, Boehm R: Ethotoin in seizures of childhood and adolescence. Neurol. 1984, 34: 791-795.
    • (1984) Neurol , vol.34 , pp. 791-795
    • Carter, C.A.1    Helms, R.A.2    Boehm, R.3
  • 5
    • 0025084679 scopus 로고
    • Sodium channel binding and anticonvulsant activities of hydantoins containing conformationally constrained 5-phenyl substituents
    • Brouillette WJ, Brown GB, DeLorey TM, Liang G: Sodium channel binding and anticonvulsant activities of hydantoins containing conformationally constrained 5-phenyl substituents. J Pharm Sci. 1990, 79: 871-874. 10.1002/jps.2600791005.
    • (1990) J Pharm Sci , vol.79 , pp. 871-874
    • Brouillette, W.J.1    Brown, G.B.2    DeLorey, T.M.3    Liang, G.4
  • 6
    • 0031052522 scopus 로고    scopus 로고
    • Effects of log P and phenyl ring conformation on the binding of 5-phenylhydantoins to the voltage-dependent sodium channel
    • Brown ML, Brown GB, Brouillette WJ: Effects of log P and phenyl ring conformation on the binding of 5-phenylhydantoins to the voltage-dependent sodium channel. J Med Chem. 1997, 40: 602-607. 10.1021/jm960692v.
    • (1997) J Med Chem , vol.40 , pp. 602-607
    • Brown, M.L.1    Brown, G.B.2    Brouillette, W.J.3
  • 7
    • 0018846765 scopus 로고
    • Receptor modeling for anticonvulsant and convulsant drugs. Antiepileptic Drugs: Mechanism of Action
    • Edited by: Glasser GH, Penry JK, Woodbury DM., New York: Raven Press
    • Smythies JR: Receptor modeling for anticonvulsant and convulsant drugs. Antiepileptic Drugs: Mechanism of Action. Edited by: Glasser GH, Penry JK, Woodbury DM. 1980, New York: Raven Press, 207-222.
    • (1980) , pp. 207-222
    • Smythies, J.R.1
  • 8
    • 0021332122 scopus 로고
    • Structure-activity relationships of phenytoin-like anticonvulsant drugs
    • Poupaert JH, Vandervorst D, Guiot P, Moustafa MMM, Dumont P: Structure-activity relationships of phenytoin-like anticonvulsant drugs. J Med Chem. 1984, 27: 76-78. 10.1021/jm00367a015.
    • (1984) J Med Chem , vol.27 , pp. 76-78
    • Poupaert, J.H.1    Vandervorst, D.2    Guiot, P.3    Moustafa, M.M.M.4    Dumont, P.5
  • 9
    • 0021999826 scopus 로고
    • Effect of structural modification of the hydantoin ring on anticonvulsant activity
    • Cortes S, Liao ZK, Watson D, Kohn H: Effect of structural modification of the hydantoin ring on anticonvulsant activity. J Med Chem. 1985, 28: 601-606. 10.1021/jm50001a012.
    • (1985) J Med Chem , vol.28 , pp. 601-606
    • Cortes, S.1    Liao, Z.K.2    Watson, D.3    Kohn, H.4
  • 10
    • 3342980671 scopus 로고    scopus 로고
    • 5,5-Diphenyl-2-thiohydantoin
    • Roszak AW, Weaver DF: 5,5-Diphenyl-2-thiohydantoin. Acta Cryst C. 1998, 54: 1168-1170. 10.1107/S0108270197019963.
    • (1998) Acta Cryst C , vol.54 , pp. 1168-1170
    • Roszak, A.W.1    Weaver, D.F.2
  • 11
    • 0000918660 scopus 로고    scopus 로고
    • The influence of structure and lipophilicity of hydantoin derivatives on anticonvulsant activity
    • Scholl S, Koch A, Henning D, Kempter G, Kleinpeter E: The influence of structure and lipophilicity of hydantoin derivatives on anticonvulsant activity. Struct Chem. 1999, 10: 355-366. 10.1023/A:1022091411018.
    • (1999) Struct Chem , vol.10 , pp. 355-366
    • Scholl, S.1    Koch, A.2    Henning, D.3    Kempter, G.4    Kleinpeter, E.5
  • 12
    • 0026037184 scopus 로고
    • Role of hydrogen bonding in general anesthesia
    • Abraham MH, Lieb WR, Franks NP: Role of hydrogen bonding in general anesthesia. J Pharm Sci. 1991, 80: 719-724. 10.1002/jps.2600800802.
    • (1991) J Pharm Sci , vol.80 , pp. 719-724
    • Abraham, M.H.1    Lieb, W.R.2    Franks, N.P.3
  • 13
    • 19444386240 scopus 로고
    • Application of solvation equations to chemical and biochemical processes
    • Abraham MH: Application of solvation equations to chemical and biochemical processes. Pure Appl Chem. 1993, 65: 2503-2512. 10.1351/pac199365122503.
    • (1993) Pure Appl Chem , vol.65 , pp. 2503-2512
    • Abraham, M.H.1
  • 15
    • 79953807997 scopus 로고    scopus 로고
    • Reversed-phase TLC and HPLC retention data in correlation studies with in silico molecular descriptors and druglikeness droperties of newly synthesized anticonvulsant succinimide derivatives
    • Perišić-Janjić N, Kaliszan R, Wiczling P, Milošević N, Ušćumlić G, Banjac N: Reversed-phase TLC and HPLC retention data in correlation studies with in silico molecular descriptors and druglikeness droperties of newly synthesized anticonvulsant succinimide derivatives. Mol Pharmaceut. 2011, 8: 555-563. 10.1021/mp100373d.
    • (2011) Mol Pharmaceut , vol.8 , pp. 555-563
    • Perišić-Janjić, N.1    Kaliszan, R.2    Wiczling, P.3    Milošević, N.4    Ušćumlić, G.5    Banjac, N.6
  • 16
    • 0041573625 scopus 로고
    • Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, Π, α, and β, and some methods for simplifying the generalized solvatochromic equation
    • Kamlet MJ, Abboud JLM, Abraham MH, Taft RW: Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, Π, α, and β, and some methods for simplifying the generalized solvatochromic equation. J Org Chem. 1983, 48: 2877-2887. 10.1021/jo00165a018.
    • (1983) J Org Chem , vol.48 , pp. 2877-2887
    • Kamlet, M.J.1    Abboud, J.L.M.2    Abraham, M.H.3    Taft, R.W.4
  • 17
    • 34249681314 scopus 로고    scopus 로고
    • Solvent effects on the structure-activity relationship of pharmacological active 3-substituted-5,5-diphenylhydantoins
    • Banjac N, Ušćumlić G, Valentić N, Mijin D: Solvent effects on the structure-activity relationship of pharmacological active 3-substituted-5,5-diphenylhydantoins. J Solution Chem. 2007, 36: 869-878. 10.1007/s10953-007-9153-2.
    • (2007) J Solution Chem , vol.36 , pp. 869-878
    • Banjac, N.1    Ušćumlić, G.2    Valentić, N.3    Mijin, D.4
  • 18
    • 62549135656 scopus 로고    scopus 로고
    • Solvent effects on the structure-activity relationship of phenytoin-like anticonvulsant drugs
    • Trišović N, Banjac N, Valentić N, Ušćumlić G: Solvent effects on the structure-activity relationship of phenytoin-like anticonvulsant drugs. J Solution Chem. 2009, 38: 199-208. 10.1007/s10953-008-9367-y.
    • (2009) J Solution Chem , vol.38 , pp. 199-208
    • Trišović, N.1    Banjac, N.2    Valentić, N.3    Ušćumlić, G.4
  • 19
    • 0002889538 scopus 로고
    • Syntheses of hydantoins. II. Formation of substituted hydantoins from aldehydes and ketones
    • Bucherer HT, Lieb VA: Syntheses of hydantoins. II. Formation of substituted hydantoins from aldehydes and ketones. J Prakt Chem. 1934, 141: 5-43. 10.1002/prac.19341410102.
    • (1934) J Prakt Chem , vol.141 , pp. 5-43
    • Bucherer, H.T.1    Lieb, V.A.2
  • 20
    • 3543038251 scopus 로고    scopus 로고
    • Active-site characteristics of CYP2C19 and CYP2C9 probed with hydantoin and barbiturate inhibitors
    • Suzuki H, Kneller MB, Rock DA, Jones JP, Trager WF, Rettie AE: Active-site characteristics of CYP2C19 and CYP2C9 probed with hydantoin and barbiturate inhibitors. Arch Biochem Biophys. 2004, 429: 1-15. 10.1016/j.abb.2004.05.015.
    • (2004) Arch Biochem Biophys , vol.429 , pp. 1-15
    • Suzuki, H.1    Kneller, M.B.2    Rock, D.A.3    Jones, J.P.4    Trager, W.F.5    Rettie, A.E.6
  • 22
    • 84855666555 scopus 로고    scopus 로고
    • Synthesis, structure and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins
    • Trišović N, Valentić N, Erović M, Daković-Sekulić T, Ušćumlić G, Juranić I: Synthesis, structure and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins. Monats Chem. 10.1007/s00706-011-0639-7. doi:10.1007/s00706-011-0639-7.
    • Monats Chem.
    • Trišović, N.1    Valentić, N.2    Erović, M.3    Daković-Sekulić, T.4    Ušćumlić, G.5    Juranić, I.6
  • 23
    • 0006469110 scopus 로고
    • The properties of organic liquids that are relevant to their use as solvating solvents
    • Marcus Y: The properties of organic liquids that are relevant to their use as solvating solvents. Chem Soc Rev. 1993, 22: 409-416. 10.1039/cs9932200409.
    • (1993) Chem Soc Rev , vol.22 , pp. 409-416
    • Marcus, Y.1
  • 24
    • 0347862482 scopus 로고
    • The influence of the solvent on organic reactivity. Part 5. Kinetics of the reaction of diazodiphenylmethane with benzoic acid in branched-chain alkanols and in electronegatively substituted alcohols
    • Mather D, Shorter J: The influence of the solvent on organic reactivity. Part 5. Kinetics of the reaction of diazodiphenylmethane with benzoic acid in branched-chain alkanols and in electronegatively substituted alcohols. J Chem Soc Perkin Trans II. 1983, 1179-1183.
    • (1983) J Chem Soc Perkin Trans II. , pp. 1179-1183
    • Mather, D.1    Shorter, J.2
  • 25
    • 53849098405 scopus 로고    scopus 로고
    • Differentiating between dipolarity and polarizability effects of solvents using the solvatochromism of barbiturate dyes
    • Bauer M, Rollberg A, Barth A, Spange S: Differentiating between dipolarity and polarizability effects of solvents using the solvatochromism of barbiturate dyes. Eur J Org Chem. 2008, 4475-4481.
    • (2008) Eur J Org Chem. , pp. 4475-4481
    • Bauer, M.1    Rollberg, A.2    Barth, A.3    Spange, S.4
  • 26
    • 37049154962 scopus 로고
    • The absorption spectra of organic compounds containing nitrogen. I. Derivatives of hydantoin
    • Stuckey RE: The absorption spectra of organic compounds containing nitrogen. I. Derivatives of hydantoin. J Chem Soc. 1947, 169: 331-334.
    • (1947) J Chem Soc , vol.169 , pp. 331-334
    • Stuckey, R.E.1
  • 27
    • 37049075581 scopus 로고
    • Ionization constants of 5-arylmethylenehydantoins in 80% (w/w) dimethyl sulfoxide-water at 25°
    • Tan SF, Ang KP, Fong YF, Jayachandran H: Ionization constants of 5-arylmethylenehydantoins in 80% (w/w) dimethyl sulfoxide-water at 25°. J Chem Soc Perkin Trans II. 1988, 473-476.
    • (1988) J Chem Soc Perkin Trans II. , pp. 473-476
    • Tan, S.F.1    Ang, K.P.2    Fong, Y.F.3    Jayachandran, H.4
  • 28
    • 84970948081 scopus 로고    scopus 로고
    • Solvents and Solvent Effects in Organic Chemistry
    • Weinheim: Wiley - VCH
    • Reinchard C: Solvents and Solvent Effects in Organic Chemistry. 2003, Weinheim: Wiley - VCH, 457.
    • (2003) , pp. 457
    • Reinchard, C.1
  • 29
    • 84986550210 scopus 로고
    • Quantitative models of steric effects
    • Unger SH, Hansch C: Quantitative models of steric effects. Prog Phys Org Chem. 1976, 12: 91-118.
    • (1976) Prog Phys Org Chem , vol.12 , pp. 91-118
    • Unger, S.H.1    Hansch, C.2
  • 30
    • 0018850819 scopus 로고
    • Quantitative mechanistic studies in simultaneous fluid flow and intestinal absorption using steroids as model solutes
    • Komiya I, Park JY, Kamani A, Ho NFH, Higuchi WI: Quantitative mechanistic studies in simultaneous fluid flow and intestinal absorption using steroids as model solutes. Int J Pharm. 1980, 4: 249-262. 10.1016/0378-5173(80)90140-4.
    • (1980) Int J Pharm , vol.4 , pp. 249-262
    • Komiya, I.1    Park, J.Y.2    Kamani, A.3    Ho, N.F.H.4    Higuchi, W.I.5
  • 31
    • 0022000211 scopus 로고
    • The absorption of β-adrenoceptor antagonists in rat in-situ small intestine the effect of lipophilicity
    • Taylor DC, Pownwall R, Burke W: The absorption of β-adrenoceptor antagonists in rat in-situ small intestine the effect of lipophilicity. J Pharm Pharmacol. 1985, 37: 280-283.
    • (1985) J Pharm Pharmacol , vol.37 , pp. 280-283
    • Taylor, D.C.1    Pownwall, R.2    Burke, W.3
  • 32
    • 0019124032 scopus 로고
    • Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability
    • Levin VA: Relationship of octanol/water partition coefficient and molecular weight to rat brain capillary permeability. J Med Chem. 1980, 23: 682-684. 10.1021/jm00180a022.
    • (1980) J Med Chem , vol.23 , pp. 682-684
    • Levin, V.A.1
  • 33
    • 0025311288 scopus 로고
    • Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorptive (Caco-2) cells
    • Artursson P: Epithelial transport of drugs in cell culture. I: A model for studying the passive diffusion of drugs over intestinal absorptive (Caco-2) cells. J Pharm Sci. 1990, 79: 476-482. 10.1002/jps.2600790604.
    • (1990) J Pharm Sci , vol.79 , pp. 476-482
    • Artursson, P.1
  • 34
    • 0029872476 scopus 로고    scopus 로고
    • Permeability of 5-fluorouracil and prodrugs in Caco-2 cell monolayers
    • Buur A, Trier L, Magnusson C, Artursson P: Permeability of 5-fluorouracil and prodrugs in Caco-2 cell monolayers. Int J Pharm. 1996, 129: 223-231. 10.1016/0378-5173(95)04331-4.
    • (1996) Int J Pharm , vol.129 , pp. 223-231
    • Buur, A.1    Trier, L.2    Magnusson, C.3    Artursson, P.4
  • 35
    • 0034992583 scopus 로고    scopus 로고
    • Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors
    • Zhao YH, Le J, Abraham MH, Hersey A, Eddershaw PJ, Luscombe CN, Boutina D, Beck G, Sherborne B, Cooper I, Platts JA: Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure-activity relationship (QSAR) with the Abraham descriptors. J Pharm Sci. 2001, 90: 749-784. 10.1002/jps.1031.
    • (2001) J Pharm Sci , vol.90 , pp. 749-784
    • Zhao, Y.H.1    Le, J.2    Abraham, M.H.3    Hersey, A.4    Eddershaw, P.J.5    Luscombe, C.N.6    Boutina, D.7    Beck, G.8    Sherborne, B.9    Cooper, I.10    Platts, J.A.11
  • 36
    • 0345306239 scopus 로고    scopus 로고
    • Quantitative relationship between rat intestinal absorption and Abraham descriptors
    • Zhao YH, Abraham MH, Hersey A, Luscombe CN: Quantitative relationship between rat intestinal absorption and Abraham descriptors. Eur J Med Chem. 2003, 38: 939-947. 10.1016/j.ejmech.2003.07.005.
    • (2003) Eur J Med Chem , vol.38 , pp. 939-947
    • Zhao, Y.H.1    Abraham, M.H.2    Hersey, A.3    Luscombe, C.N.4
  • 37
    • 0023546523 scopus 로고
    • Hydrophobicity and central nervous system agents: on the principle of minimal hydrophobicity in drug design
    • Hansch C, Björkroth JP, Leo A: Hydrophobicity and central nervous system agents: on the principle of minimal hydrophobicity in drug design. J Pharm Sci. 1987, 76: 663-687. 10.1002/jps.2600760902.
    • (1987) J Pharm Sci , vol.76 , pp. 663-687
    • Hansch, C.1    Björkroth, J.P.2    Leo, A.3
  • 39
    • 0030462889 scopus 로고    scopus 로고
    • Computation of brain-blood partitioning of organic solutes via free energy calculations
    • Lombardo F, Blake JF, Curatolo WJ: Computation of brain-blood partitioning of organic solutes via free energy calculations. J Med Chem. 1996, 39: 4750-4755. 10.1021/jm960163r.
    • (1996) J Med Chem , vol.39 , pp. 4750-4755
    • Lombardo, F.1    Blake, J.F.2    Curatolo, W.J.3
  • 40
    • 0037480602 scopus 로고    scopus 로고
    • ADME evaluation in drug discovery. 1. Applications of genetic algorithms to the prediction of blood-brain partitioning of a large set of drugs
    • Hou T, Xu X: ADME evaluation in drug discovery. 1. Applications of genetic algorithms to the prediction of blood-brain partitioning of a large set of drugs. J Mol Model. 2002, 8: 337-349.
    • (2002) J Mol Model , vol.8 , pp. 337-349
    • Hou, T.1    Xu, X.2
  • 41
    • 0037204545 scopus 로고    scopus 로고
    • Computational approaches to the prediction of the blood-brain distribution
    • Norinder U, Haeberlein M: Computational approaches to the prediction of the blood-brain distribution. Adv Drug Deliv Rev. 2002, 54: 291-313. 10.1016/S0169-409X(02)00005-4.
    • (2002) Adv Drug Deliv Rev , vol.54 , pp. 291-313
    • Norinder, U.1    Haeberlein, M.2
  • 43
    • 33746868917 scopus 로고    scopus 로고
    • Reversible binding of some isoxazolyl penicillins with serum albumin using fluorescence spectroscopic technique
    • Seedher N, Agarwal P: Reversible binding of some isoxazolyl penicillins with serum albumin using fluorescence spectroscopic technique. Ind J Pharm Sci. 2006, 68: 327-331. 10.4103/0250-474X.26667.
    • (2006) Ind J Pharm Sci , vol.68 , pp. 327-331
    • Seedher, N.1    Agarwal, P.2


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