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Volumn 48, Issue , 2012, Pages 338-346

Synthesis and anticonvulsant activity of 1-(8-(benzyloxy)quinolin-2-yl)-6- substituted-4,6-diazaspiro[2,4]heptane-5,7-diones

Author keywords

1 (8 (Benzyloxy)quinolin 2 yl 6 substituted 4,6 diazaspiro 2,4 heptane 5, 7 diones; Anticonvulsant activity; MES test; scPTZ test

Indexed keywords

1 [8 (BENZYLOXY)QUINOLIN 2 YL] 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 (1 HYDROXYBUTAN 2 YL) 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 (4 BROMOPHENYL) 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 (4 CHLOROPHENYL) 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 (4 FLUOROPHENYL) 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 (4 METHOXYPHENYL) 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 (4 NITROPHENYL) 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 4 TOLYL 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 [4 (TRIFLUOROMETHYL)PHENYL] 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 BUTYL 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 CYCLOHEXYL 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 ISOPROPYL 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 METHYL 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 6 PHENYL 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; 6 BENZYL 1 [8 (BENZYLOXY)QUINOLIN 2 YL] 4,6 DIAZASPIRO[2,4]HEPTANE 5,7 DIONE; ANTICONVULSIVE AGENT; CARBAMAZEPINE; ETHOSUXIMIDE; PHENOBARBITAL; PHENYTOIN; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; VALPROIC ACID;

EID: 84855983336     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.12.037     Document Type: Article
Times cited : (18)

References (36)
  • 1
    • 16344387731 scopus 로고    scopus 로고
    • Epileptic seizures and epilepsy: Definitions proposed by the International League Against Epilepsy (ILAE) and the International Bureau for Epilepsy (IBE)
    • DOI 10.1111/j.0013-9580.2005.66104.x
    • R.S. Fisher, W. Emde Boas, W. Blume, C. Elger, and P. Genton Epileptic seizures and epilepsy: definitions proposed by the International League against epilepsy (ILAE) and the International Bureau for epilepsy (IBE) Epilepsia 46 2005 470 472 (Pubitemid 40470667)
    • (2005) Epilepsia , vol.46 , Issue.4 , pp. 470-472
    • Fisher, R.S.1    Van Emde Boas, W.2    Blume, W.3    Elger, C.4    Genton, P.5    Lee, P.6    Engel Jr., J.7
  • 2
    • 77955437092 scopus 로고    scopus 로고
    • The structure-activity relationship of the 3-oxy site in the anticonvulsant (R)-N-benzyl 2-acetamido-3-methoxypropionamide
    • P. Morieux, C. Salom, K.D. Park, J.P. Stables, and H. Kohn The structure-activity relationship of the 3-oxy site in the anticonvulsant (R)-N-benzyl 2-acetamido-3-methoxypropionamide J. Med. Chem. 53 2010 5716 5726
    • (2010) J. Med. Chem. , vol.53 , pp. 5716-5726
    • Morieux, P.1    Salom, C.2    Park, K.D.3    Stables, J.P.4    Kohn, H.5
  • 3
    • 34547828792 scopus 로고    scopus 로고
    • Development of new antiepileptic drugs: Challenges, incentives, and recent advances
    • DOI 10.1016/S1474-4422(07)70215-6, PII S1474442207702156
    • E. Perucca, J. French, and M. Bialer Development of new antiepileptic drugs: challenges, incentives, and recent advance Lancet Neurol. 6 2007 793 804 (Pubitemid 47243712)
    • (2007) Lancet Neurology , vol.6 , Issue.9 , pp. 793-804
    • Perucca, E.1    French, J.2    Bialer, M.3
  • 4
    • 33846194013 scopus 로고    scopus 로고
    • Progress report on new antiepileptic drugs: A summary of the Eigth Eilat Conference (EILAT VIII)
    • DOI 10.1016/j.eplepsyres.2006.10.008, PII S0920121106004244
    • M. Bialer, S.I. Johannessen, H.J. Kupferberg, R.H. Levy, and E. Perucca Progress report on new antiepileptic drugs: a summary of the Eigth Eilat Conference (EILAT VIII) Epilepsy Res. 73 2007 1 52 (Pubitemid 46091734)
    • (2007) Epilepsy Research , vol.73 , Issue.1 , pp. 1-52
    • Bialer, M.1    Johannessen, S.I.2    Kupferberg, H.J.3    Levy, R.H.4    Perucca, E.5    Tomson, T.6
  • 5
    • 33846228427 scopus 로고    scopus 로고
    • Valproic Acid: Second Generation
    • DOI 10.1016/j.nurt.2006.11.007, PII S1933721306001863, New Antiepileptic Drugs: Discovery, Development, and Update
    • M. Bialer, and B. Yagen Valproic acid: second generation Neurotherapeutics 4 2007 130 137 (Pubitemid 46107326)
    • (2007) Neurotherapeutics , vol.4 , Issue.1 , pp. 130-137
    • Bialer, M.1    Yagen, B.2
  • 6
    • 77957179936 scopus 로고
    • Pharmacologic evaluation of various metabolites and analogs of valproic acid: Teratogenic potencies in mice
    • H. Nau, and W. Loscher Fundam. Pharmacologic evaluation of various metabolites and analogs of valproic acid: teratogenic potencies in mice Appl. Toxicol. 6 1986 669 676 (Pubitemid 16110138)
    • (1986) Fundamental and Applied Toxicology , vol.6 , Issue.4 , pp. 669-676
    • Nau, H.1    Loscher, W.2
  • 7
    • 0041866161 scopus 로고    scopus 로고
    • Newer anticonvulsants: Dosing strategies and cognition in treating patients with mood disorders and epilepsy
    • K.J. Meador Newer anticonvulsants: dosing strategies and cognition in treating patients with mood disorders and epilepsy J. Clin. Psychiatry 64 Suppl. 8 2003 30 34 (Pubitemid 36903905)
    • (2003) Journal of Clinical Psychiatry , vol.64 , Issue.SUPPL. 8 , pp. 30-34
    • Meador, K.J.1
  • 8
    • 0030724836 scopus 로고    scopus 로고
    • Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents
    • DOI 10.1002/(SICI)1098-1128(199711)17:6<537::AID-MED3>3.0.CO;2-2
    • Z. Lin, and P.K. Kadaba Molecular targets for the rational design of antiepileptic drugs and related neuroprotective agents Med. Res. Rev. 17 1997 537 572 (Pubitemid 27489491)
    • (1997) Medicinal Research Reviews , vol.17 , Issue.6 , pp. 537-572
    • Lin, Z.1    Kadaba, P.K.2
  • 9
    • 0035811449 scopus 로고    scopus 로고
    • Synthesis and antibacterial evaluation of certain quinolone derivatives
    • Y.L. Chen, K.C. Fang, J.Y. Shen, S.L. Hsu, and C.C. Tzeng Synthesis and antibacterial evaluation of certain quinolone derivatives J. Med. Chem. 44 2001 2374 2386
    • (2001) J. Med. Chem. , vol.44 , pp. 2374-2386
    • Chen, Y.L.1    Fang, K.C.2    Shen, J.Y.3    Hsu, S.L.4    Tzeng, C.C.5
  • 11
    • 0034736150 scopus 로고    scopus 로고
    • 4-aminoquinolines: Novel nociceptin antagonists with analgesic activity
    • H. Shinkai, T. Ito, T. Ida, Y. Kitao, H. Yamadu, and I. Uchida 4-aminoquinolines: novel nociceptin antagonists with analgesic activity J. Med. Chem. 43 2000 4667 4672
    • (2000) J. Med. Chem. , vol.43 , pp. 4667-4672
    • Shinkai, H.1    Ito, T.2    Ida, T.3    Kitao, Y.4    Yamadu, H.5    Uchida, I.6
  • 14
    • 0037030607 scopus 로고    scopus 로고
    • 3-Aryl-2-quinolone derivatives: Synthesis and characterization of in vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration
    • DOI 10.1021/jm010978m
    • B. Joseph, F. Darro, A. Behard, B. Lesur, F. Collignon, C. Decaestecker, A. Frydman, G. Guillaumet, and R. Kiss 3-Aryl-2-quinolone derivatives: synthesis and characterization of In vitro and in vivo antitumor effects with emphasis on a new therapeutical target connected with cell migration J. Med. Chem. 45 2002 2543 2555 (Pubitemid 34595224)
    • (2002) Journal of Medicinal Chemistry , vol.45 , Issue.12 , pp. 2543-2555
    • Joseph, B.1    Darro, F.2    Behard, A.3    Lesur, B.4    Collignon, F.5    Decaestecker, C.6    Frydman, A.7    Guillaumet, G.8    Kiss, R.9
  • 16
    • 0035310335 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores
    • DOI 10.1016/S0223-5234(00)01206-X, PII S022352340001206X
    • B. Ho, A. Michael Crider, and J.P. Stables Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores Eur. J. Med. Chem. 36 2001 265 286 (Pubitemid 32406202)
    • (2001) European Journal of Medicinal Chemistry , vol.36 , Issue.3 , pp. 265-286
    • Ho, B.1    Michael Crider, A.2    Stables, J.P.3
  • 17
    • 0004364857 scopus 로고
    • New series of anticonvulsant drugs. Branched-chain α- aminoacetamides
    • S.D. Upham, and O.C. Dermer New series of anticonvulsant drugs. Branched-chain α-aminoacetamides J. Org. Chem. 22 1957 799 802
    • (1957) J. Org. Chem. , vol.22 , pp. 799-802
    • Upham, S.D.1    Dermer, O.C.2
  • 19
    • 77955554691 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6- diazaspiro[2.4] heptane-5,7-diones
    • X. He, G. Qiu, J. Yang, Y. Xiao, Z. Wu, G. Qiu, and X. Hu Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4] heptane-5,7-diones Eur. J. Med. Chem. 45 2010 3818 3830
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 3818-3830
    • He, X.1    Qiu, G.2    Yang, J.3    Xiao, Y.4    Wu, Z.5    Qiu, G.6    Hu, X.7
  • 20
    • 78649334120 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant activity of N-3-arylamide substituted 5,5-cyclopropanespirohydantoin derivatives
    • X. He, M. Zhong, T. Zhang, W. Wu, Z. Wu, J. Yang, Y. Xiao, Y. Pan, G. Qiu, and X. Hu Synthesis and anticonvulsant activity of N-3-arylamide substituted 5,5-cyclopropanespirohydantoin derivatives Eur. J. Med. Chem. 45 2010 5870 5877
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 5870-5877
    • He, X.1    Zhong, M.2    Zhang, T.3    Wu, W.4    Wu, Z.5    Yang, J.6    Xiao, Y.7    Pan, Y.8    Qiu, G.9    Hu, X.10
  • 21
    • 57949097927 scopus 로고    scopus 로고
    • Synthesis and potential anticonvulsant activity of new N-3-substituted 5,5-cyclopropanespirohydantoins
    • Q. Zhu, Y. Pan, Z. Xu, R. Li, G. Qiu, W. Xu, X. Ke, L. Wu, and X. Hu Synthesis and potential anticonvulsant activity of new N-3-substituted 5,5-cyclopropanespirohydantoins Eur. J. Med. Chem. 44 2009 296 302
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 296-302
    • Zhu, Q.1    Pan, Y.2    Xu, Z.3    Li, R.4    Qiu, G.5    Xu, W.6    Ke, X.7    Wu, L.8    Hu, X.9
  • 24
    • 0000449303 scopus 로고
    • Dichloroethylaluminum-catalyzed reactions of alkenes with electrophilic cyclopropanes. A new cyclopentane annelation reaction
    • R.B. Beal, M.A. Dombroski, and B.B. Snider Dichloroethylaluminum- catalyzed reactions of alkenes with electrophilic cyclopropanes. A new cyclopentane annelation reaction J. Org. Chem. 51 1986 4391 4399
    • (1986) J. Org. Chem. , vol.51 , pp. 4391-4399
    • Beal, R.B.1    Dombroski, M.A.2    Snider, B.B.3
  • 25
    • 0028567706 scopus 로고
    • Straightforward synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via selective saponification of 2,2-dialkylcyclopropane-1,1-dicarboxylic esters and Curtius rearrangement
    • N. Kimpe, and M. Boeykens Straightforward synthesis of 1-amino-2,2-dialkylcyclopropanecarboxylic acids via selective saponification of 2,2-dialkylcyclopropane-1,1-dicarboxylic esters and Curtius rearrangement J. Org. Chem. 59 1994 8215 8219
    • (1994) J. Org. Chem. , vol.59 , pp. 8215-8219
    • Kimpe, N.1    Boeykens, M.2
  • 26
    • 3042798891 scopus 로고    scopus 로고
    • The neurobiology of antiepileptic drugs
    • M.A. Rogawski, and W. Löscher The neurobiology of antiepileptic drugs Nat. Rev. Neurosci. 5 2004 553 564 (Pubitemid 38868551)
    • (2004) Nature Reviews Neuroscience , vol.5 , Issue.7 , pp. 553-564
    • Rogawski, M.A.1    Loscher, W.2
  • 27
    • 0018423267 scopus 로고
    • Quantitative structure-activity relationships and dipole moments of anticonvulsants and CNS depressants
    • DOI 10.1002/jps.2600680418
    • E.J. Lien, R.C. Liao, and H.G. Shinouda Quantitative structure-activity relationships and dipole moments of anticonvulsants and CNS depressants J. Pharm. Sci. 68 1979 463 465 (Pubitemid 9168935)
    • (1979) Journal of Pharmaceutical Sciences , vol.68 , Issue.4 , pp. 463-465
    • Lien, E.J.1    Liao, R.C.H.2    Shinouda, H.G.3
  • 28
    • 0018129707 scopus 로고
    • Antiepileptic drug development: II. Anticonvulsant drug screening
    • R.L. Krall, J.K. Penry, B.G. White, H.J. Kupferberg, and E.A. Swinyard Antiepileptic drug development: II. anticonvulsant drug screening Epilepsia 19 1978 409 428 (Pubitemid 9016848)
    • (1978) Epilepsia , vol.19 , Issue.4 , pp. 409-428
    • Krall, R.L.1    Penry, J.K.2    White, B.G.3
  • 29
    • 77952708293 scopus 로고    scopus 로고
    • Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4-aminobenzensulfonamide
    • N. Hen, M. Bialer, B. Wlodarczyk, R.H. Finnell, and B. Yagen Syntheses and evaluation of anticonvulsant profile and teratogenicity of novel amide derivatives of branched aliphatic carboxylic acids with 4-aminobenzensulfonamide J. Med. Chem. 53 2010 4177 4186
    • (2010) J. Med. Chem. , vol.53 , pp. 4177-4186
    • Hen, N.1    Bialer, M.2    Wlodarczyk, B.3    Finnell, R.H.4    Yagen, B.5
  • 30
    • 0014524862 scopus 로고
    • Laboratory evaluation of antiepileptic drugs. Review of laboratory methods
    • E.A. Swinyard Laboratory evaluation of antiepileptic drugs. Review of laboratory methods Epilepsia 10 1969 107 119
    • (1969) Epilepsia , vol.10 , pp. 107-119
    • Swinyard, E.A.1
  • 31
    • 0032572830 scopus 로고    scopus 로고
    • Anticonvulsant activity and interactions with neuronal voltage- dependent sodium channel of analogues of ameltolide
    • DOI 10.1021/jm9608772
    • J. Vamecq, D. Lambert, J.H. Poupaert, B. Masereel, and J.P. Stables Anticonvulsant activity and interactions with neuronal voltage-dependent sodium channel of analogs of ameltolide J. Med. Chem. 41 1998 3307 3313 (Pubitemid 28406537)
    • (1998) Journal of Medicinal Chemistry , vol.41 , Issue.18 , pp. 3307-3313
    • Vamecq, J.1    Lambert, D.2    Poupaert, J.H.3    Masereel, B.4    Stables, J.P.5
  • 32
    • 70449179373 scopus 로고
    • The pharmacological activity of a series of basic esters of mono- and dialkylmalonic acids
    • N.W. Dunham, T.A. Miya, and L.D. Edwards The pharmacological activity of a series of basic esters of mono- and dialkylmalonic acids J. Am. Pharm. Assoc. 46 1957 64 66
    • (1957) J. Am. Pharm. Assoc. , vol.46 , pp. 64-66
    • Dunham, N.W.1    Miya, T.A.2    Edwards, L.D.3
  • 34
    • 0029053795 scopus 로고
    • Evaluation of the semicarbazones, thiosemicarbazones and bis-carbohydrazones of some aryl alicyclic ketones for anticonvulsant and other biological properties
    • J.R. Dimmock, S.N. Pandey, J.W. Quail, U. Pugazhenthi, T.M. Allen, G.Y. Kao, J. Balzarini, and E. DeClercq Evaluation of the semicarbazones, thiosemicarbazones and bis-carbohydrazones of some aryl alicyclic ketones for anticonvulsant and other biological properties Eur. J. Med. Chem. 30 1995 303 314
    • (1995) Eur. J. Med. Chem. , vol.30 , pp. 303-314
    • Dimmock, J.R.1    Pandey, S.N.2    Quail, J.W.3    Pugazhenthi, U.4    Allen, T.M.5    Kao, G.Y.6    Balzarini, J.7    Declercq, E.8
  • 35
    • 68249112815 scopus 로고    scopus 로고
    • Synthesis of novel 2,5-disubstituted 1,3,4-thiadiazoles for their potential anticonvulsant activity: Pharmacophoric model studies
    • H. Rajak, R. Deshmukh, N. Aggarwal, S. Kashaw, M.D. Kharya, and P. Mishra Synthesis of novel 2,5-disubstituted 1,3,4-thiadiazoles for their potential anticonvulsant activity: pharmacophoric model studies Arch. Pharm. 342 2009 453 461
    • (2009) Arch. Pharm. , vol.342 , pp. 453-461
    • Rajak, H.1    Deshmukh, R.2    Aggarwal, N.3    Kashaw, S.4    Kharya, M.D.5    Mishra, P.6


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