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      KCI등재 SCIE SCOPUS

      Phenytoin-based Bivalent Ligands: Design, Synthesis and Anticonvulsant Activity

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      https://www.riss.kr/link?id=A104666486

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      다국어 초록 (Multilingual Abstract)

      Synthesis, characterization and anticonvulsant properties of new bivalent ligands derived from phenytoin were described. Initial anticonvulsant screening was performed using maximal electroshock (MES) and pentylenetetrazole (PTZ) screens in mice. The neurotoxicity for compounds that showed significant anticonvulsant activity was determined applying the rotorod test. Most of the test compounds were found to be effective in at least one seizure model in a dose of 100 mg/kg. Compound 5e exhibited marked anticonvulsant activity in both MES and PTZ screens. The computer-aided prediction of biological activity was carried out.
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      Synthesis, characterization and anticonvulsant properties of new bivalent ligands derived from phenytoin were described. Initial anticonvulsant screening was performed using maximal electroshock (MES) and pentylenetetrazole (PTZ) screens in mice. The ...

      Synthesis, characterization and anticonvulsant properties of new bivalent ligands derived from phenytoin were described. Initial anticonvulsant screening was performed using maximal electroshock (MES) and pentylenetetrazole (PTZ) screens in mice. The neurotoxicity for compounds that showed significant anticonvulsant activity was determined applying the rotorod test. Most of the test compounds were found to be effective in at least one seizure model in a dose of 100 mg/kg. Compound 5e exhibited marked anticonvulsant activity in both MES and PTZ screens. The computer-aided prediction of biological activity was carried out.

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      참고문헌 (Reference)

      1 Schlögl, K., "Zur kenntnis der hydantoinpeptide" 83 : 493-512, 1952

      2 Löscher, W., "The role of technical, biological and pharmacological factors in the laboratory evaluation of anticonvulsant drugs, III : Pentylenetetrazole seizure models" 8 : 171-189, 1991

      3 Scheurer, M. L., "The evaluation and treatment of seizures" 323 : 1468-1474, 1990

      4 Poupaert, J. H., "Synthesis of bivalent ligands derived from phenytoin" 97 : 469-470, 1988

      5 Zha, C., "Synthesis and structure-activity relationship studies for hydantoins and analogues as voltage-gated sodium channel ligands" 47 : 6519-6528, 2004

      6 Obniska, J., "Synthesis and anticonvulsant activity of new N-[(4-arylpiperazin-1-yl)-alkyl] derivatives of 3-phenyl-pyrrolidine-2, 5-dione" 44 : 2224-2233, 2009

      7 Kaminski, K., "Synthesis and anticonvulsant activity of new 1-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]pyrrolidine-2, 5-diones" 21 : 5800-5803, 2011

      8 Pandeya, S. N., "Synthesis and anticonvulsant activity of 4-bromophenyl substituted aryl semicarbazones" 35 : 879-886, 2000

      9 Zhao, Y. H., "Rate-limited steps of human oral absorption and QSAR studies" 19 : 1446-1457, 2002

      10 Paxton, J. W., "Production and characterisation of antisera to diphenylhydantoin suitable for radioimmunoassay" 10 : 317-327, 1976

      1 Schlögl, K., "Zur kenntnis der hydantoinpeptide" 83 : 493-512, 1952

      2 Löscher, W., "The role of technical, biological and pharmacological factors in the laboratory evaluation of anticonvulsant drugs, III : Pentylenetetrazole seizure models" 8 : 171-189, 1991

      3 Scheurer, M. L., "The evaluation and treatment of seizures" 323 : 1468-1474, 1990

      4 Poupaert, J. H., "Synthesis of bivalent ligands derived from phenytoin" 97 : 469-470, 1988

      5 Zha, C., "Synthesis and structure-activity relationship studies for hydantoins and analogues as voltage-gated sodium channel ligands" 47 : 6519-6528, 2004

      6 Obniska, J., "Synthesis and anticonvulsant activity of new N-[(4-arylpiperazin-1-yl)-alkyl] derivatives of 3-phenyl-pyrrolidine-2, 5-dione" 44 : 2224-2233, 2009

      7 Kaminski, K., "Synthesis and anticonvulsant activity of new 1-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]pyrrolidine-2, 5-diones" 21 : 5800-5803, 2011

      8 Pandeya, S. N., "Synthesis and anticonvulsant activity of 4-bromophenyl substituted aryl semicarbazones" 35 : 879-886, 2000

      9 Zhao, Y. H., "Rate-limited steps of human oral absorption and QSAR studies" 19 : 1446-1457, 2002

      10 Paxton, J. W., "Production and characterisation of antisera to diphenylhydantoin suitable for radioimmunoassay" 10 : 317-327, 1976

      11 Hudkins, R. L., "Phenytoin derivatives as potent σ-ligands" 4 : 2185-2188, 1994

      12 Löscher, W., "New visions in the pharmacology of anticonvulsion" 342 : 1-13, 1998

      13 Löscher, W., "New horizons in the development of antiepileptic drugs : Innovative strategies" 69 : 183-272, 2006

      14 Wright, D., "Multivalent binding in the design of bioactive compounds" 5 : 1107-1131, 2001

      15 Rogawski, M. A., "Molecular targets versus models for new antiepileptic drug discovery" 68 : 22-28, 2006

      16 Veber, D. F., "Molecular properties that influence the oral bioavailability of drug candidates" 45 : 2615-2623, 2002

      17 Ahsan, M. J., "Molecular properties prediction and synthesis of novel 1, 3, 4-oxadiazole analogues as potential antimicrobial agents" 21 : 7246-7250, 2011

      18 Upton, N., "Mechanisms of action of new antiepileptic drugs : rational design and serendipitous findings" 15 : 456-463, 1994

      19 Kitano, Y., "Increasing-current electroshock seizure test : A new method for assessment of anti-and pro-convulsant activities of drugs in mice" 35 : 25-29, 1996

      20 Refsgaard, H. H., "In silico prediction of membrane permeability from calculated molecular parameters" 48 : 805-811, 2005

      21 George, S. R., "G-protein-coupled receptor oligomerization and its potential for drug discovery" 1 : 808-820, 2002

      22 Lipinski, C. A., "Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings" 46 : 3-26, 2001

      23 Dimmock, J. R., "Evaluation of the semicarbazones, thiosemicarbazones and bis-carbohydrazones of some aryl alicycylic ketones for anticonvulsant and other biological properties" 30 : 303-314, 1995

      24 Ouchi, M., "Convenient and efficient tosylation of oligoethylene glycosl and the related alcohols in tetrahydrofuran-water in the presence of sodium hydroxide" 63 : 1260-1262, 1990

      25 Löscher, W., "Comparative evaluation of anticonvulsant and toxic potencies of valproic acid and 2-en-valproic acid in different animal models of epilepsy" 99 : 211-218, 1984

      26 Huber, D., "Bivalent molecular probes for dopamine D2-like receptors" 20 : 455-466, 2012

      27 Cuadrado, A., "Beneficial interactions between vigabatrin and valproate against seizures induced by pentylenetetrazole in mice" 51 : 489-496, 2005

      28 Krall, R. L., "Antiepileptic drug development : II. Anticonvulsant drug screening" 19 : 409-428, 1998

      29 Fisher, R. S., "Animal models of the epilepsies" 14 : 245-278, 1989

      30 Cramer, J. A., "Adverse effects of antiepileptic drugs : a brief overview of important issues" 10 : 885-891, 2010

      31 Greenwood, R. S., "Adverse effects of antiepileptic drugs" 41 : 42-52, 2000

      32 Lenkowski, P. W., "A pharmacophore derived phenytoin analogue with increased affinity for slow inactivated sodium channels exhibits a desired anticonvulsant profile" 52 : 1044-1054, 2007

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      2023 평가예정 해외DB학술지평가 신청대상 (해외등재 학술지 평가)
      2020-01-01 평가 등재학술지 유지 (해외등재 학술지 평가) KCI등재
      2010-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2008-01-01 평가 등재학술지 유지 (등재유지) KCI등재
      2006-01-01 평가 등재학술지 유지 (등재유지) KCI등재
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      학술지 인용정보
      기준연도 WOS-KCI 통합IF(2년) KCIF(2년) KCIF(3년)
      2016 1.96 0.2 1.44
      KCIF(4년) KCIF(5년) 중심성지수(3년) 즉시성지수
      1.07 0.87 0.439 0.05
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