메뉴 건너뛰기




Volumn 22, Issue 11, 1997, Pages 1210-1220

Epibatidine

Author keywords

[No Author keywords available]

Indexed keywords

ANALGESIC AGENT; EPIBATIDINE; MECAMYLAMINE; NICOTINIC RECEPTOR;

EID: 0031469705     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey
Times cited : (25)

References (56)
  • 1
    • 0001650460 scopus 로고
    • Synthetic approaches to epibatidine
    • For recent reviews on epibatidine see: (a) Broka, C.A. Synthetic approaches to epibatidine. Med Chem Res 1994, 4: 449-60. (b) Szántay, C., Kardos-Balogh, Z., Szántay, C. Jr. Epibatidine. In: The Alkaloids, Vol. 46, G.A. Cordell (Ed.), Academic Press, San Diego, 1995, 95-125. (c) Kellar, K.J. Epibatidine: Its pharmacological actions and utility for studying neuronal nicotinic receptors. Neurotransmissions 1995, 11: 1-5. (d) Sullivan, J.P., Bannon, A.W. Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent. CNS Drug Rev 1996, 2: 21-39. (e) Chen, Z., Trudell, M.L. Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]hepatanes. Chem Rev 1996, 96: 1179-93.
    • (1994) Med Chem Res , vol.4 , pp. 449-460
    • Broka, C.A.1
  • 2
    • 77957045898 scopus 로고
    • Epibatidine
    • G.A. Cordell (Ed.), Academic Press, San Diego
    • For recent reviews on epibatidine see: (a) Broka, C.A. Synthetic approaches to epibatidine. Med Chem Res 1994, 4: 449-60. (b) Szántay, C., Kardos-Balogh, Z., Szántay, C. Jr. Epibatidine. In: The Alkaloids, Vol. 46, G.A. Cordell (Ed.), Academic Press, San Diego, 1995, 95-125. (c) Kellar, K.J. Epibatidine: Its pharmacological actions and utility for studying neuronal nicotinic receptors. Neurotransmissions 1995, 11: 1-5. (d) Sullivan, J.P., Bannon, A.W. Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent. CNS Drug Rev 1996, 2: 21-39. (e) Chen, Z., Trudell, M.L. Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]hepatanes. Chem Rev 1996, 96: 1179-93.
    • (1995) The Alkaloids , vol.46 , pp. 95-125
    • Szántay, C.1    Kardos-Balogh, Z.2    Szántay Jr., C.3
  • 3
    • 0342326488 scopus 로고
    • Epibatidine: Its pharmacological actions and utility for studying neuronal nicotinic receptors
    • For recent reviews on epibatidine see: (a) Broka, C.A. Synthetic approaches to epibatidine. Med Chem Res 1994, 4: 449-60. (b) Szántay, C., Kardos-Balogh, Z., Szántay, C. Jr. Epibatidine. In: The Alkaloids, Vol. 46, G.A. Cordell (Ed.), Academic Press, San Diego, 1995, 95-125. (c) Kellar, K.J. Epibatidine: Its pharmacological actions and utility for studying neuronal nicotinic receptors. Neurotransmissions 1995, 11: 1-5. (d) Sullivan, J.P., Bannon, A.W. Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent. CNS Drug Rev 1996, 2: 21-39. (e) Chen, Z., Trudell, M.L. Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]hepatanes. Chem Rev 1996, 96: 1179-93.
    • (1995) Neurotransmissions , vol.11 , pp. 1-5
    • Kellar, K.J.1
  • 4
    • 0029921513 scopus 로고    scopus 로고
    • Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent
    • For recent reviews on epibatidine see: (a) Broka, C.A. Synthetic approaches to epibatidine. Med Chem Res 1994, 4: 449-60. (b) Szántay, C., Kardos-Balogh, Z., Szántay, C. Jr. Epibatidine. In: The Alkaloids, Vol. 46, G.A. Cordell (Ed.), Academic Press, San Diego, 1995, 95-125. (c) Kellar, K.J. Epibatidine: Its pharmacological actions and utility for studying neuronal nicotinic receptors. Neurotransmissions 1995, 11: 1-5. (d) Sullivan, J.P., Bannon, A.W. Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent. CNS Drug Rev 1996, 2: 21-39. (e) Chen, Z., Trudell, M.L. Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]hepatanes. Chem Rev 1996, 96: 1179-93.
    • (1996) CNS Drug Rev , vol.2 , pp. 21-39
    • Sullivan, J.P.1    Bannon, A.W.2
  • 5
    • 0000140103 scopus 로고    scopus 로고
    • Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]hepatanes
    • For recent reviews on epibatidine see: (a) Broka, C.A. Synthetic approaches to epibatidine. Med Chem Res 1994, 4: 449-60. (b) Szántay, C., Kardos-Balogh, Z., Szántay, C. Jr. Epibatidine. In: The Alkaloids, Vol. 46, G.A. Cordell (Ed.), Academic Press, San Diego, 1995, 95-125. (c) Kellar, K.J. Epibatidine: Its pharmacological actions and utility for studying neuronal nicotinic receptors. Neurotransmissions 1995, 11: 1-5. (d) Sullivan, J.P., Bannon, A.W. Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent. CNS Drug Rev 1996, 2: 21-39. (e) Chen, Z., Trudell, M.L. Chemistry of 7-azabicyclo[2.2.1]hepta-2,5-dienes, 7-azabicyclo[2.2.1]hept-2-enes, and 7-azabicyclo[2.2.1]hepatanes. Chem Rev 1996, 96: 1179-93.
    • (1996) Chem Rev , vol.96 , pp. 1179-1193
    • Chen, Z.1    Trudell, M.L.2
  • 6
    • 0026551490 scopus 로고
    • Epibatidine: A novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog
    • Spande, T.F., Garraffo, H.M., Edwards, M.W., Yeh, H.J.C., Pannel, L., Daly, J.W. Epibatidine: A novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog. J Amer Chem Soc 1992, 114: 3475-8.
    • (1992) J Amer Chem Soc , vol.114 , pp. 3475-3478
    • Spande, T.F.1    Garraffo, H.M.2    Edwards, M.W.3    Yeh, H.J.C.4    Pannel, L.5    Daly, J.W.6
  • 7
    • 0027154034 scopus 로고
    • Total synthesis of epibatidine
    • Broka, C.A. Total synthesis of epibatidine. Tetrahedron Lett 1993, 34: 3251-4.
    • (1993) Tetrahedron Lett , vol.34 , pp. 3251-3254
    • Broka, C.A.1
  • 14
    • 84986984213 scopus 로고
    • Synthesis and biological evaluation of (±)-epibatidine and the congeners
    • Senokuchi, K., Nakai, H., Kawamura, M. et al. Synthesis and biological evaluation of (±)-epibatidine and the congeners. Synlett 1994, 343-4.
    • (1994) Synlett , pp. 343-344
    • Senokuchi, K.1    Nakai, H.2    Kawamura, M.3
  • 17
    • 0030583492 scopus 로고    scopus 로고
    • An asymmetric synthesis of (-)-epibatidine
    • Trost, B.M., Cook, G.R. An asymmetric synthesis of (-)-epibatidine. Tetrahedron Lett 1996, 37: 7485-8.
    • (1996) Tetrahedron Lett , vol.37 , pp. 7485-7488
    • Trost, B.M.1    Cook, G.R.2
  • 18
    • 0031023040 scopus 로고    scopus 로고
    • Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine
    • Albertini, E., Barco, A., Benetti, S., De Risi, C., Pollini, G.P., Zanirato, V. Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine. Tetrahedron Lett 1997, 38: 681-4.
    • (1997) Tetrahedron Lett , vol.38 , pp. 681-684
    • Albertini, E.1    Barco, A.2    Benetti, S.3    De Risi, C.4    Pollini, G.P.5    Zanirato, V.6
  • 19
    • 0028954581 scopus 로고
    • A simple method of preparation of 7-alkyl-7-azabicyclo[2.2.1]heptanes
    • Hassner, A., Belostotskii, A.M. A simple method of preparation of 7-alkyl-7-azabicyclo[2.2.1]heptanes. Tetrahedron Lett 1995, 36: 1709-12.
    • (1995) Tetrahedron Lett , vol.36 , pp. 1709-1712
    • Hassner, A.1    Belostotskii, A.M.2
  • 21
    • 0027291373 scopus 로고
    • A versatile total synthesis of epibatidine and analogs
    • Huang, D.F., Shen, T.Y. A versatile total synthesis of epibatidine and analogs. Tetrahedron Lett 1993, 34: 4477-80.
    • (1993) Tetrahedron Lett , vol.34 , pp. 4477-4480
    • Huang, D.F.1    Shen, T.Y.2
  • 22
    • 0028821678 scopus 로고
    • Synthesis of (+) and (-) epibatidine
    • Kotian, P.L., Carrol, F.I. Synthesis of (+) and (-) epibatidine. Synth Commun 1995, 25: 63-71.
    • (1995) Synth Commun , vol.25 , pp. 63-71
    • Kotian, P.L.1    Carrol, F.I.2
  • 23
    • 0027373899 scopus 로고
    • A total synthesis of (±)-epibatidine
    • Clayton, S.C., Regan, A.C. A total synthesis of (±)-epibatidine. Tetrahedron Lett 1993, 34: 7493-6.
    • (1993) Tetrahedron Lett , vol.34 , pp. 7493-7496
    • Clayton, S.C.1    Regan, A.C.2
  • 24
    • 0027993480 scopus 로고
    • Total synthesis of a frog poison, (±)-epibatidine, a potent non-opioid analgesic
    • Okabe, K., Natsume, M. Total synthesis of a frog poison, (±)-epibatidine, a potent non-opioid analgesic. Chem Pharm Bull 1994, 42: 1432-6.
    • (1994) Chem Pharm Bull , vol.42 , pp. 1432-1436
    • Okabe, K.1    Natsume, M.2
  • 25
    • 0029822637 scopus 로고    scopus 로고
    • A short and efficient total synthesis of (±)-epibatidine
    • Zhang, C., Trudell, M.L. A short and efficient total synthesis of (±)-epibatidine. J Org Chem 1996, 61: 7189-91.
    • (1996) J Org Chem , vol.61 , pp. 7189-7191
    • Zhang, C.1    Trudell, M.L.2
  • 26
    • 0027969038 scopus 로고
    • An expeditious synthesis of epibatidine and analogues
    • Pandey, G., Bagul, T.D., Lakshmaiah, G. An expeditious synthesis of epibatidine and analogues. Tetrahedron Lett 1994, 35: 7439-42.
    • (1994) Tetrahedron Lett , vol.35 , pp. 7439-7442
    • Pandey, G.1    Bagul, T.D.2    Lakshmaiah, G.3
  • 27
    • 0029920516 scopus 로고    scopus 로고
    • Total synthesis of (±)-epibatidine
    • Xu, R., Chu, G., Bai, D. Total synthesis of (±)-epibatidine. Tetrahedron Lett 1996, 37: 1463-6.
    • (1996) Tetrahedron Lett , vol.37 , pp. 1463-1466
    • Xu, R.1    Chu, G.2    Bai, D.3
  • 28
    • 0344298556 scopus 로고    scopus 로고
    • Synthesis of (±)-epibatidine and its analogues
    • Bai, D., Xu, R., Chu, G., Zhu, X. Synthesis of (±)-epibatidine and its analogues. J Org Chem 1996, 61: 4600-6.
    • (1996) J Org Chem , vol.61 , pp. 4600-4606
    • Bai, D.1    Xu, R.2    Chu, G.3    Zhu, X.4
  • 29
    • 0029045992 scopus 로고
    • Synthesis of (+)- and (-)-N-BOC-7-azabicyclo[2.2.1]heptan-2-ones, versatile intermediates for the enantiospecific synthesis of (+)- and (-)-epibatidine and analogues
    • Hernández, A., Marcos, M., Rapoport, H. Synthesis of (+)- and (-)-N-BOC-7-azabicyclo[2.2.1]heptan-2-ones, versatile intermediates for the enantiospecific synthesis of (+)- and (-)-epibatidine and analogues. J Org Chem 1995, 60: 2638-91.
    • (1995) J Org Chem , vol.60 , pp. 2638-2691
    • Hernández, A.1    Marcos, M.2    Rapoport, H.3
  • 33
    • 0029927101 scopus 로고    scopus 로고
    • Evaluation of anti-nociceptive effects of neuronal nicotinic acetylcholine receptor (nAChR) ligands in the rat tail-flick assay
    • Rao, T.S., Correa, L.D., Reid, R.T., Lloyd, G.K. Evaluation of anti-nociceptive effects of neuronal nicotinic acetylcholine receptor (nAChR) ligands in the rat tail-flick assay. Neuropharmacology 1996, 35: 393-405.
    • (1996) Neuropharmacology , vol.35 , pp. 393-405
    • Rao, T.S.1    Correa, L.D.2    Reid, R.T.3    Lloyd, G.K.4
  • 34
    • 0000727741 scopus 로고
    • (+)-Epibatidine can differentially evoke responses mediated by putative subtypes of nicotinic acetylcholine receptors (nAChRs)
    • Sullivan, J.P., Briggs, C.A., Donnelly, D. et al. (+)-Epibatidine can differentially evoke responses mediated by putative subtypes of nicotinic acetylcholine receptors (nAChRs). Med Chem Res 1994, 4: 502-16.
    • (1994) Med Chem Res , vol.4 , pp. 502-516
    • Sullivan, J.P.1    Briggs, C.A.2    Donnelly, D.3
  • 35
    • 0028172276 scopus 로고
    • (+)-Epibatidine elicits a diversity of in vitro and in vivo effects mediated by nicotinic acetylcholine receptors
    • Sullivan, J.P., Decker, M.W., Brioni, J.D. et al. (+)-Epibatidine elicits a diversity of in vitro and in vivo effects mediated by nicotinic acetylcholine receptors. J Pharmacol Exp Ther 1994, 271: 624-31.
    • (1994) J Pharmacol Exp Ther , vol.271 , pp. 624-631
    • Sullivan, J.P.1    Decker, M.W.2    Brioni, J.D.3
  • 36
    • 0028230727 scopus 로고
    • Epibatidine, a potent analgetic and nicotinic agonist
    • Badio, B., Daly, J.W. Epibatidine, a potent analgetic and nicotinic agonist. Mol Pharmacol 1994, 45: 562-9.
    • (1994) Mol Pharmacol , vol.45 , pp. 562-569
    • Badio, B.1    Daly, J.W.2
  • 37
    • 0001679612 scopus 로고
    • Epibatidine: Discovery and definition as a potent analgesic and nicotinic agonist
    • Badio, B., Garraffo, H.M., Spande, T.F., Daly, J.W. Epibatidine: Discovery and definition as a potent analgesic and nicotinic agonist. Med Chem Res 1994, 4: 440-8.
    • (1994) Med Chem Res , vol.4 , pp. 440-448
    • Badio, B.1    Garraffo, H.M.2    Spande, T.F.3    Daly, J.W.4
  • 38
    • 0028997458 scopus 로고
    • Is epibatidine really analgesic? Dissociation of the locomotor activity, temperature, and analgesic effects of (+)-epibatidine
    • Bannon, A.W., Gunther, K.L., Decker, M.W. Is epibatidine really analgesic? Dissociation of the locomotor activity, temperature, and analgesic effects of (+)-epibatidine. Pharmacol Biochem Behav 1995, 51: 693-8.
    • (1995) Pharmacol Biochem Behav , vol.51 , pp. 693-698
    • Bannon, A.W.1    Gunther, K.L.2    Decker, M.W.3
  • 39
    • 0028933123 scopus 로고
    • The influence of Bay K 8644 treatment on (+)-epibatidine-induced analgesia
    • Bannon, A.W., Gunther, K.L., Decker, M.W., Arneric, S.P. The influence of Bay K 8644 treatment on (+)-epibatidine-induced analgesia. Brain Res 1995, 678: 244-50.
    • (1995) Brain Res , vol.678 , pp. 244-250
    • Bannon, A.W.1    Gunther, K.L.2    Decker, M.W.3    Arneric, S.P.4
  • 42
    • 0000205033 scopus 로고
    • Analgesic activity of epibatidine and its enantiomers in a chemical model of pain in mice
    • Damaj, M.I., Tucker, S.M., Aceto, M.D., Martin, B.R. Analgesic activity of epibatidine and its enantiomers in a chemical model of pain in mice. Med Chem Res 1994, 4: 483-92.
    • (1994) Med Chem Res , vol.4 , pp. 483-492
    • Damaj, M.I.1    Tucker, S.M.2    Aceto, M.D.3    Martin, B.R.4
  • 43
    • 0013656413 scopus 로고    scopus 로고
    • Tolerance to the antinociceptive effect of epibatidine after acute and chronic administration in mice
    • Damaj, M.I., Martin, B.R. Tolerance to the antinociceptive effect of epibatidine after acute and chronic administration in mice. Eur J Pharmacol 1996, 300: 51-7.
    • (1996) Eur J Pharmacol , vol.300 , pp. 51-57
    • Damaj, M.I.1    Martin, B.R.2
  • 44
    • 0000821928 scopus 로고    scopus 로고
    • Epibatidine, a potent nicotinic agonist: Effects on learning and memory in the radial-arm maze
    • Levin, E.D., Toll, K., Chang, G., Christopher, N.C., Briggs, S.J., Fiedler, W. Epibatidine, a potent nicotinic agonist: Effects on learning and memory in the radial-arm maze. Med Chem Res 1996, 543-4.
    • (1996) Med Chem Res , pp. 543-544
    • Levin, E.D.1    Toll, K.2    Chang, G.3    Christopher, N.C.4    Briggs, S.J.5    Fiedler, W.6
  • 45
    • 0030175612 scopus 로고    scopus 로고
    • Nicotinic receptors in the development and modulation of CNS synapses
    • Role, L.W., Berg, D.K. Nicotinic receptors in the development and modulation of CNS synapses. Neuron 1996, 16: 1077-85.
    • (1996) Neuron , vol.16 , pp. 1077-1085
    • Role, L.W.1    Berg, D.K.2
  • 47
    • 0029416936 scopus 로고
    • 3H]-Epibatidine labels nicotinic receptors in rat brain: An autoradiographic study
    • 3H]-Epibatidine labels nicotinic receptors in rat brain: An autoradiographic study. J Pharmacol Exp Ther 1995, 275: 1030-4.
    • (1995) J Pharmacol Exp Ther , vol.275 , pp. 1030-1034
    • Perry, D.C.1    Kellar, K.J.2
  • 48
    • 0029566105 scopus 로고
    • In vivo labeling of neuronal nicotinic acetylcholine receptors with radiolabeled isomers of norchloroepibatidine
    • Scheffel, U., Taylor, G.F., Kepler, J.A., Carroll, F.I., Kuhar, M.J. In vivo labeling of neuronal nicotinic acetylcholine receptors with radiolabeled isomers of norchloroepibatidine. NeuroReport 1995, 6: 2483-8.
    • (1995) NeuroReport , vol.6 , pp. 2483-2488
    • Scheffel, U.1    Taylor, G.F.2    Kepler, J.A.3    Carroll, F.I.4    Kuhar, M.J.5
  • 51
    • 0346213872 scopus 로고
    • Stable expression and pharmacologic properties of the human neuronal nicotinic acetylcholine receptor α-4 β-2 subtype
    • Sullivan, J.P., Monteggia, L.M., Anderson, D.J., Giordano, T.G., Arneric, S.P., Gopalakrishnan, M. Stable expression and pharmacologic properties of the human neuronal nicotinic acetylcholine receptor α-4 β-2 subtype. FASEB J 1995, 9: S2262.
    • (1995) FASEB J , vol.9
    • Sullivan, J.P.1    Monteggia, L.M.2    Anderson, D.J.3    Giordano, T.G.4    Arneric, S.P.5    Gopalakrishnan, M.6
  • 52
    • 0029800519 scopus 로고    scopus 로고
    • Pharmacological characterization of a nicotinic autoreceptor in rat hippocampal synaptosomes
    • Wilkie, G.I., Hutson, P., Sullivan, J.P., Wonnacott, S. Pharmacological characterization of a nicotinic autoreceptor in rat hippocampal synaptosomes. Neurochem Res 1996, 21: 1141-8.
    • (1996) Neurochem Res , vol.21 , pp. 1141-1148
    • Wilkie, G.I.1    Hutson, P.2    Sullivan, J.P.3    Wonnacott, S.4
  • 53
    • 0030088073 scopus 로고    scopus 로고
    • Epibatidine, a nicotinic acetylcholine receptor agonist releases monoaminergic neurotransmitters: In vitro and in vivo evidence in rats
    • Sacaan, A.I., Menzaghi, F., Dunlop, J.L., Correa, L.D., Whelan, K.T., Lloyd, G.K. Epibatidine, a nicotinic acetylcholine receptor agonist releases monoaminergic neurotransmitters: In vitro and in vivo evidence in rats. J Pharmacol Exp Ther 1996, 276: 509-15.
    • (1996) J Pharmacol Exp Ther , vol.276 , pp. 509-515
    • Sacaan, A.I.1    Menzaghi, F.2    Dunlop, J.L.3    Correa, L.D.4    Whelan, K.T.5    Lloyd, G.K.6
  • 54
    • 0030438472 scopus 로고    scopus 로고
    • Intrathecal nicotinic agonist-elicited release of excitatory amino acids as measured by in vivo spinal microdialysis in rats
    • Khan, I.M., Marsala, M., Printz, M.P., Taylor, P., Yaksh, T.L. Intrathecal nicotinic agonist-elicited release of excitatory amino acids as measured by in vivo spinal microdialysis in rats. J Pharmacol Exp Ther 1996, 278: 97-106.
    • (1996) J Pharmacol Exp Ther , vol.278 , pp. 97-106
    • Khan, I.M.1    Marsala, M.2    Printz, M.P.3    Taylor, P.4    Yaksh, T.L.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.