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Volumn 39, Issue 9, 1996, Pages 1928-1934

Synthesis and pharmacological properties of novel 8-substituted imidazobenzodiazepines: High-affinity, selective probes for α5-containing GABAA receptors

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID A RECEPTOR; 4 ETHYL 6,7 DIMETHOXY BETA CARBOLINE 3 CARBOXYLIC ACID METHYL ESTER; 5,6 DIHYDRO 5 METHYL 6 OXO 8 [(TRIMETHYLSILYL)ETHYNYL] 4H IMIDAZO[1,5 A][1,4]BENZODIAZEPINE 3 CARBOXYLIC ACID ETHYL ESTER; 5,6 DIHYDRO 5 METHYL 6 OXO 8 [(TRIMETHYLSILYL)ETHYNYL] 4H IMIDAZO[1,5 A][1,4]BENZODIAZEPINE 3 CARBOXYLIC ACID TERT BUTYL ESTER; 8 AZIDO 5,6 DIHYDRO 5 METHYL 6 OXO 4H IMIDAZO[1,5 A][1,4]BENZODIAZEPINE 3 CARBOXYLIC ACID ETHYL ESTER; 8 ETHYNYL 5,6 DIHYDRO 5 METHYL 6 OXO 4H IMIDAZO[1,5 A][1,4]BENZODIAZEPINE 3 CARBOXYLIC ACID ETHYL ESTER; 8 ETHYNYL 5,6 DIHYDRO 5 METHYL 6 OXO 4H IMIDAZO[1,5 A][1,4]BENZODIAZEPINE 3 CARBOXYLIC ACID TERT BUTYL ESTER; ANTICONVULSIVE AGENT; BENZODIAZEPINE DERIVATIVE; CONVULSANT AGENT; DIAZEPAM; FLUMAZENIL; FLUNITRAZEPAM; IMIDAZOBENZODIAZEPINE DERIVATIVE; RO 14 4513; RO 15 1310; TRITIUM; UNCLASSIFIED DRUG; ZOLPIDEM;

EID: 0029881508     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950887n     Document Type: Article
Times cited : (85)

References (37)
  • 1
    • 0000810035 scopus 로고
    • A/benzodiazepine receptor subtype
    • A/benzodiazepine receptor subtype. Med. Chem. Res. 1995, 5, 700-709. Liu, R.; Zhang, P.; Gillard, N. P.; McKernan, R. M.; Cook, J. M. Synthesis of ligands selective for the α5 benzodiazepine receptor (BzR) subtype. Presented at the 209th ACS National Meeting, Anaheim, CA, April 2-6, 1995, MedI 1. Liu, R.; Gillard, N. P.; Gu, Z. G.; Rice, K.; McKernan, R. M.; Cook, J. M. Search for α5 benzodiazepine receptor subtype specific ligands based on the structure of sarmazenil (Ro15-4513). Presented at the 56th Annual Scientific Meeting of the College on Problems of Drug Dependence, the Breakers, West Palm Beach, FL, June 18-23, 1994, Oral Communications VI.
    • (1995) Med. Chem. Res. , vol.5 , pp. 700-709
    • Liu, R.1    Zhang, P.2    McKernan, R.M.3    Wafford, K.4    Cook, J.M.5
  • 2
    • 15644383698 scopus 로고
    • Synthesis of ligands selective for the α5 benzodiazepine receptor (BzR) subtype
    • Anaheim, CA, April 2-6, MedI 1
    • A/benzodiazepine receptor subtype. Med. Chem. Res. 1995, 5, 700-709. Liu, R.; Zhang, P.; Gillard, N. P.; McKernan, R. M.; Cook, J. M. Synthesis of ligands selective for the α5 benzodiazepine receptor (BzR) subtype. Presented at the 209th ACS National Meeting, Anaheim, CA, April 2-6, 1995, MedI 1. Liu, R.; Gillard, N. P.; Gu, Z. G.; Rice, K.; McKernan, R. M.; Cook, J. M. Search for α5 benzodiazepine receptor subtype specific ligands based on the structure of sarmazenil (Ro15-4513). Presented at the 56th Annual Scientific Meeting of the College on Problems of Drug Dependence, the Breakers, West Palm Beach, FL, June 18-23, 1994, Oral Communications VI.
    • (1995) 209th ACS National Meeting
    • Liu, R.1    Zhang, P.2    Gillard, N.P.3    McKernan, R.M.4    Cook, J.M.5
  • 3
    • 1842628902 scopus 로고
    • Search for α5 benzodiazepine receptor subtype specific ligands based on the structure of sarmazenil (Ro15-4513)
    • the Breakers, West Palm Beach, FL, June 18-23, Oral Communications VI
    • A/benzodiazepine receptor subtype. Med. Chem. Res. 1995, 5, 700-709. Liu, R.; Zhang, P.; Gillard, N. P.; McKernan, R. M.; Cook, J. M. Synthesis of ligands selective for the α5 benzodiazepine receptor (BzR) subtype. Presented at the 209th ACS National Meeting, Anaheim, CA, April 2-6, 1995, Medl 1. Liu, R.; Gillard, N. P.; Gu, Z. G.; Rice, K.; McKernan, R. M.; Cook, J. M. Search for α5 benzodiazepine receptor subtype specific ligands based on the structure of sarmazenil (Ro15-4513). Presented at the 56th Annual Scientific Meeting of the College on Problems of Drug Dependence, the Breakers, West Palm Beach, FL, June 18-23, 1994, Oral Communications VI.
    • (1994) 56th Annual Scientific Meeting of the College on Problems of Drug Dependence
    • Liu, R.1    Gillard, N.P.2    Gu, Z.G.3    Rice, K.4    McKernan, R.M.5    Cook, J.M.6
  • 4
    • 0023898813 scopus 로고
    • The benzodiazepine/GABA receptor chloride channel complex
    • Skolnick, P.; Paul, S. The benzodiazepine/GABA receptor chloride channel complex. ISI Atlas Pharmacol. 1988, 2, 19-22.
    • (1988) ISI Atlas Pharmacol. , vol.2 , pp. 19-22
    • Skolnick, P.1    Paul, S.2
  • 5
    • 0026501358 scopus 로고
    • Multiple benzodiazepine receptors: No reason for anxiety
    • Doble, A.; Martin, I. L. Multiple benzodiazepine receptors: no reason for anxiety. Trends Pharmacol. Sci. 1992, 13, 76-81.
    • (1992) Trends Pharmacol. Sci. , vol.13 , pp. 76-81
    • Doble, A.1    Martin, I.L.2
  • 6
    • 0027976290 scopus 로고
    • Quaternary structure of the native GABA-A receptor determined by electron microscope image analysis
    • Nayeem, N.; Green, T. P.; Martin, I. L.; Barnard, E. A. Quaternary structure of the native GABA-A receptor determined by electron microscope image analysis. J. Neurochem. 1994, 62, 815-818.
    • (1994) J. Neurochem. , vol.62 , pp. 815-818
    • Nayeem, N.1    Green, T.P.2    Martin, I.L.3    Barnard, E.A.4
  • 7
    • 0028986131 scopus 로고
    • GABA-A/benzodiazepine receptor heterogeneity: Neurophysiological implications
    • Luddens, H.; Korpi, E.; Seeburg, P. GABA-A/benzodiazepine receptor heterogeneity: neurophysiological implications. Neuropharmacology 1995, 34, 245-254.
    • (1995) Neuropharmacology , vol.34 , pp. 245-254
    • Luddens, H.1    Korpi, E.2    Seeburg, P.3
  • 10
    • 0028987216 scopus 로고
    • Different subunit requirements for volatile and nonvolatile anesthetics at gamma-aminobutyric acid type A receptors
    • Harris, B. D.; Wong, G.; Moody, E. J.; Skolnick, P. Different subunit requirements for volatile and nonvolatile anesthetics at gamma-aminobutyric acid type A receptors. Mol. Pharmacol. 1995, 47, 363-367.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 363-367
    • Harris, B.D.1    Wong, G.2    Moody, E.J.3    Skolnick, P.4
  • 12
    • 0024423323 scopus 로고
    • A-benzodiazepine receptors produced in transfected cells
    • A-benzodiazepine receptors produced in transfected cells. Science 1989, 245, 1389-1392.
    • (1989) Science , vol.245 , pp. 1389-1392
    • Pritchett, D.B.1    Luddens, H.2    Seeburg, P.H.3
  • 13
    • 0028338548 scopus 로고
    • Impact of β and γ variants on ligand-binding properties of γ-aminobutyric acid type A receptors
    • Luddens, H.; Seeburg, P.; Korpi, E. Impact of β and γ variants on ligand-binding properties of γ-aminobutyric acid type A receptors. Mol. Pharmacol. 1994, 45, 810-814.
    • (1994) Mol. Pharmacol. , vol.45 , pp. 810-814
    • Luddens, H.1    Seeburg, P.2    Korpi, E.3
  • 14
    • 0025295576 scopus 로고
    • Differential benzodiazepine pharmacology of recombinant GABA-A receptors
    • Von Blankenfeld, G.; Ymer, S.; Pritchett, D. Differential benzodiazepine pharmacology of recombinant GABA-A receptors. Neurosci. Lett. 1990, 115, 269-273.
    • (1990) Neurosci. Lett. , vol.115 , pp. 269-273
    • Von Blankenfeld, G.1    Ymer, S.2    Pritchett, D.3
  • 17
    • 0026612363 scopus 로고
    • A receptor subunit mRNAs in the rat brain. I. Telencephalon, diencephalon, mesencephalon
    • A receptor subunit mRNAs in the rat brain. I. Telencephalon, diencephalon, mesencephalon. J. Neurosci. 1992, 12, 1040-1062.
    • (1992) J. Neurosci. , vol.12 , pp. 1040-1062
    • Wisden, W.1    Laurie, D.J.2    Monyer, H.3    Seeburg, P.H.4
  • 18
    • 0025193448 scopus 로고
    • A receptor alpha 5-subunit creates novel type II benzodiazepine receptor pharmacology
    • A receptor alpha 5-subunit creates novel type II benzodiazepine receptor pharmacology. J. Neurochem. 1990, 54, 1802-1804.
    • (1990) J. Neurochem. , vol.54 , pp. 1802-1804
    • Pritchett, D.B.1    Seeburg, P.H.2
  • 20
    • 0025925272 scopus 로고
    • GABA receptor subtypes immunopurified from rat brain with α-subunit specific antibodies have unique pharmacological properties
    • McKernan, R. M.; Quirk, K; Prince, R.; Cox, P. A.; Gillard, N. P.; Ragan, C. I.; Whiting, P. J. GABA receptor subtypes immunopurified from rat brain with α-subunit specific antibodies have unique pharmacological properties. Neuron 1992, 7, 667-676.
    • (1992) Neuron , vol.7 , pp. 667-676
    • McKernan, R.M.1    Quirk, K.2    Prince, R.3    Cox, P.A.4    Gillard, N.P.5    Ragan, C.I.6    Whiting, P.J.7
  • 21
    • 0027532355 scopus 로고
    • A receptor reveal brain regional heterogeneity
    • A receptor reveal brain regional heterogeneity. J. Neurochem. 1993, 60, 1388-1398.
    • (1993) J. Neurochem. , vol.60 , pp. 1388-1398
    • Endo, S.1    Olsen, R.W.2
  • 22
    • 0027297733 scopus 로고
    • Synthesis and evaluation of imidazo[1,5-α][1,4]-benzodiazepine esters with high affinities and selectivities at diazepam insensitive (DI) benzodiazdepine receptors
    • Gu, Z. Q.; Wong, G.; Dominguez, C.; de-Costa, B. R.; Rice, K. C.; Skolnick, P. Synthesis and evaluation of imidazo[1,5-α][1,4]-benzodiazepine esters with high affinities and selectivities at diazepam insensitive (DI) benzodiazdepine receptors. J. Med. Chem. 1993, 36, 1001-1006.
    • (1993) J. Med. Chem. , vol.36 , pp. 1001-1006
    • Gu, Z.Q.1    Wong, G.2    Dominguez, C.3    De-Costa, B.R.4    Rice, K.C.5    Skolnick, P.6
  • 23
    • 33845557697 scopus 로고
    • Facile synthesis of ethynylated benzoic acid derivatives and aromatic compounds via ethynyltrimethylsilane
    • Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. Facile synthesis of ethynylated benzoic acid derivatives and aromatic compounds via ethynyltrimethylsilane. J. Org. Chem. 1981, 46, 2280-2286.
    • (1981) J. Org. Chem. , vol.46 , pp. 2280-2286
    • Austin, W.B.1    Bilow, N.2    Kelleghan, W.J.3    Lau, K.S.Y.4
  • 24
    • 0001205056 scopus 로고
    • Preparation of a terminal allene, 3-haloallene, and 3-acylallene from a propargyltrimethylsilane
    • Flood, T.; Peterson, P. E. Preparation of a terminal allene, 3-haloallene, and 3-acylallene from a propargyltrimethylsilane. J. Org. Chem. 1980, 45, 5006-5007.
    • (1980) J. Org. Chem. , vol.45 , pp. 5006-5007
    • Flood, T.1    Peterson, P.E.2
  • 26
    • 0018672851 scopus 로고
    • A synthetic non-benzodiazepine ligand for benzodiazepine receptors: A probe for investigating neuronal substrates of anxiety
    • Lippa, A. S.; Coupet, J.; Greenblatt, E. N.; Klepner, C. A.; Beer, B. A synthetic non-benzodiazepine ligand for benzodiazepine receptors: a probe for investigating neuronal substrates of anxiety. Pharmacol. Biochem. Behav. 1979, 11, 99-106.
    • (1979) Pharmacol. Biochem. Behav. , vol.11 , pp. 99-106
    • Lippa, A.S.1    Coupet, J.2    Greenblatt, E.N.3    Klepner, C.A.4    Beer, B.5
  • 28
    • 0028912677 scopus 로고
    • Development of a comprehensive pharmacophore model for the benzodiazepine receptor
    • Zhang, W.; Koehler, K. F.; Zhang, P.; Cook, J. M. Development of a comprehensive pharmacophore model for the benzodiazepine receptor. Drug Des. Discovery 1995, 12, 193-248.
    • (1995) Drug Des. Discovery , vol.12 , pp. 193-248
    • Zhang, W.1    Koehler, K.F.2    Zhang, P.3    Cook, J.M.4
  • 30
    • 0000114679 scopus 로고
    • Urinary and brain β-carboline-3-carboxylates as potent inhibitors of brain benzodiazepine receptors
    • Braestrup, C.; Nielsen, M. C.; Olsen, C. E. Urinary and brain β-carboline-3-carboxylates as potent inhibitors of brain benzodiazepine receptors. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2288-2292.
    • (1980) Proc. Natl. Acad. Sci. U.S.A. , vol.77 , pp. 2288-2292
    • Braestrup, C.1    Nielsen, M.C.2    Olsen, C.E.3
  • 31
    • 0026438363 scopus 로고
    • A-Receptor subtypes differing in α-subunit composition display unique pharmacological properties
    • Biggio, G., Concas, A., Costa, E., Eds.; Raven Press: New York
    • A-Receptor subtypes differing in α-subunit composition display unique pharmacological properties. In GABAergic Synaptic Transmission; Biggio, G., Concas, A., Costa, E., Eds.; Raven Press: New York, 1992; pp 41-53.
    • (1992) GABAergic Synaptic Transmission , pp. 41-53
    • Mohler, H.1    Benke, D.2    Mertens, S.3    Fritschy, J.M.4
  • 33
    • 0028281108 scopus 로고
    • The synthesis of benzofused benzodiazepines employed as probes of the agonist pharmacophore of benzodiazepine receptors
    • Zhang, W.; Koehler, K. F.; Harris, B.; Skolnick, P.; Cook, J. M. The synthesis of benzofused benzodiazepines employed as probes of the agonist pharmacophore of benzodiazepine receptors. J. Med. Chem. 1994, 37, 745-757.
    • (1994) J. Med. Chem. , vol.37 , pp. 745-757
    • Zhang, W.1    Koehler, K.F.2    Harris, B.3    Skolnick, P.4    Cook, J.M.5
  • 35
    • 0025892315 scopus 로고
    • Synthetic and computer assisted analysis of the pharmacophore for agonists at benzodiazepine receptors
    • Diaz-Arauzo, H.; Koehler, K. F.; Hagen, T. J.; Cook, J. M. Synthetic and computer assisted analysis of the pharmacophore for agonists at benzodiazepine receptors. Life Sci. 1991, 49, 207-216.
    • (1991) Life Sci. , vol.49 , pp. 207-216
    • Diaz-Arauzo, H.1    Koehler, K.F.2    Hagen, T.J.3    Cook, J.M.4
  • 36
    • 0025879799 scopus 로고
    • The agonist pharmacophore of the benzodiazepine receptor. Synthesis of a selective anticonvulsant/anxiolytic
    • Diaz-Arauzo, H.; Evomuk, G. E.; Skolnick, P.; Cook, J. M. The agonist pharmacophore of the benzodiazepine receptor. Synthesis of a selective anticonvulsant/anxiolytic. J. Med. Chem. 1991, 34, 1754-1756.
    • (1991) J. Med. Chem. , vol.34 , pp. 1754-1756
    • Diaz-Arauzo, H.1    Evomuk, G.E.2    Skolnick, P.3    Cook, J.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.