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Volumn 40, Issue 5, 1997, Pages 695-704

Probes for narcotic receptor mediated phenomena. 23. Synthesis, opioid receptor binding, and bioassay of the highly selective δ agonist (+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]N,N- diethylbenzamide (SNC 80) and related novel nonpeptide δ opioid receptor ligands

Author keywords

[No Author keywords available]

Indexed keywords

4 [ALPHA (4 ALLYL 2,5 DIMETHYL 1 PIPERAZINYL) 3 METHOXYBENZYL] N,N DIETHYLBENZAMIDE; OPIATE AGONIST; UNCLASSIFIED DRUG;

EID: 14444274551     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960319n     Document Type: Article
Times cited : (78)

References (58)
  • 2
    • 0015918260 scopus 로고
    • Opiate receptor: Demonstration in Nervous Tissue
    • (a) Pert, C.; Snyder, S. Opiate receptor: Demonstration in Nervous Tissue. Science 1973, 179, 1011-1014.
    • (1973) Science , vol.179 , pp. 1011-1014
    • Pert, C.1    Snyder, S.2
  • 3
    • 0017735536 scopus 로고
    • Endogenous Opioid Peptides: Multiple Agonists and Receptors
    • (b) Lord, J.; Waterfield, A.; Hughes, J.; Kosterlitz, H. Endogenous Opioid Peptides: Multiple Agonists and Receptors. Nature 1977, 267, 495-499.
    • (1977) Nature , vol.267 , pp. 495-499
    • Lord, J.1    Waterfield, A.2    Hughes, J.3    Kosterlitz, H.4
  • 4
    • 0342381829 scopus 로고
    • The Multiplicity of Opioid Receptors and their Functional Significance
    • Berlin, Mutschler, E., Wintrfeldt, E., Eds.; VCH Verlagsgesellschaft: Weinheim
    • (c) Herz, A. The Multiplicity of Opioid Receptors and their Functional Significance. In Trends in Medicinal Chemistry: Proceedings of the 9th International Symposium on Medicinal Chemistry, Berlin, 1986; Mutschler, E., Wintrfeldt, E., Eds.; VCH Verlagsgesellschaft: Weinheim, 1987; pp 337-350.
    • (1986) Trends in Medicinal Chemistry: Proceedings of the 9th International Symposium on Medicinal Chemistry , pp. 337-350
    • Herz, A.1
  • 5
    • 0026051553 scopus 로고
    • Lack of Antinociceptive Cross-tolerance between Enkephalin and Deltorphin II in Mice: Evidence for Delta Receptor Subtypes
    • (d) Mattia, A.; Vanderah, T.; Mosberg, H. I.; Porreca, F. Lack of Antinociceptive Cross-tolerance between Enkephalin and Deltorphin II in Mice: Evidence for Delta Receptor Subtypes. J. Pharmacol. Exp. Ther. 1991, 258, 583-587.
    • (1991) J. Pharmacol. Exp. Ther. , vol.258 , pp. 583-587
    • Mattia, A.1    Vanderah, T.2    Mosberg, H.I.3    Porreca, F.4
  • 6
    • 0026456996 scopus 로고
    • Interaction of Opioid Peptides and Other Drugs with Multiple Kappa receptors in Rat and Human Brain. Evidence for Species Differences
    • (e) Rothman, R. B.; Bykov, V.; Xue, B. G.; Xu, H.; de Costa, B. R.; Jacobson, A. E.; Rice, K. C.; Kleinman, J. E.; Brady, L. S. Interaction of Opioid Peptides and Other Drugs with Multiple Kappa receptors in Rat and Human Brain. Evidence for Species Differences. Peptides 1992, 13, 977-987.
    • (1992) Peptides , vol.13 , pp. 977-987
    • Rothman, R.B.1    Bykov, V.2    Xue, B.G.3    Xu, H.4    De Costa, B.R.5    Jacobson, A.E.6    Rice, K.C.7    Kleinman, J.E.8    Brady, L.S.9
  • 8
    • 0024459590 scopus 로고
    • Multiple Opioid Receptors: Ligand Selectivity Profiles and Binding Site Signatures
    • (a) Goldstein, A.; Naidu, A. Multiple Opioid Receptors: Ligand Selectivity Profiles and Binding Site Signatures. Mol. Pharmacol. 1989, 36, 265-272.
    • (1989) Mol. Pharmacol. , vol.36 , pp. 265-272
    • Goldstein, A.1    Naidu, A.2
  • 9
    • 0028887626 scopus 로고
    • Opioid-receptor mRNA Expression in the Rat CNS: Anatomical and Functional Implications
    • (b) Mansour, A.; Fox, C. A.; Akil, H.; Watson, S. J. Opioid-receptor mRNA Expression in the Rat CNS: Anatomical and Functional Implications. Trends Neurosci. 1995, 18, 22-29.
    • (1995) Trends Neurosci. , vol.18 , pp. 22-29
    • Mansour, A.1    Fox, C.A.2    Akil, H.3    Watson, S.J.4
  • 10
    • 0025072676 scopus 로고
    • Selective Modulation of Morphine Antinociception, but Not Development of Tolerance, by δ Receptor Agonists
    • (a) Jiang, Q.; Mosberg, H. I.; Porreca, F. Selective Modulation of Morphine Antinociception, but Not Development of Tolerance, by δ Receptor Agonists. Eur. J. Pharmacol. 1990, 186, 137-141.
    • (1990) Eur. J. Pharmacol. , vol.186 , pp. 137-141
    • Jiang, Q.1    Mosberg, H.I.2    Porreca, F.3
  • 11
    • 0026550559 scopus 로고
    • Antinociceptive Interactions of Opioid Delta Receptor Agonists with Morphine in Mice: Supra- and Sub-Additivity
    • (b) Horan, P.; Tallarida, R. J.; Haaseth, R. C.; Matsunaga, T. O.; Hruby, V. J.; Porreca, F. Antinociceptive Interactions of Opioid Delta Receptor Agonists with Morphine in Mice: Supra- and Sub-Additivity. Life Sci. 1992, 50, 1535-1541.
    • (1992) Life Sci. , vol.50 , pp. 1535-1541
    • Horan, P.1    Tallarida, R.J.2    Haaseth, R.C.3    Matsunaga, T.O.4    Hruby, V.J.5    Porreca, F.6
  • 13
    • 0343967922 scopus 로고
    • Pharmacological Mechanisms of Pain Modulation. An Update on δ Opioid Receptors
    • Chapman, C. R., Foley, K. M., Eds.; Raven Press, Ltd.: New York
    • (d) Hammond, D. L. Pharmacological Mechanisms of Pain Modulation. An Update on δ Opioid Receptors. In Current and Emerging Issues in Cancer Pain: Research and Practice; Chapman, C. R., Foley, K. M., Eds.; Raven Press, Ltd.: New York, 1993; pp 175-183.
    • (1993) Current and Emerging Issues in Cancer Pain: Research and Practice , pp. 175-183
    • Hammond, D.L.1
  • 14
    • 0025107375 scopus 로고
    • The Effects of Opioid Peptides on Dopamine Release in the Nucleus Accumbens: An in Vivo Microdialysis Study
    • (a) Spanagel, R.; Herz, A.; Shippenberg, T. S. The Effects of Opioid Peptides on Dopamine Release in the Nucleus Accumbens: An In Vivo Microdialysis Study. J. Neurochem. 1990, 55, 1734-1739.
    • (1990) J. Neurochem. , vol.55 , pp. 1734-1739
    • Spanagel, R.1    Herz, A.2    Shippenberg, T.S.3
  • 15
    • 0026559951 scopus 로고
    • Opposing Tonically Active Endogenous Opioid Systems Modulate the Mesolimbic Dopaminergic Pathway
    • (b) Spanagel, R.; Herz, A.; Shippenberg, T. S. Opposing Tonically Active Endogenous Opioid Systems Modulate the Mesolimbic Dopaminergic Pathway. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2046-2050. Manzanares, J.; Durham, R. A.; Lookingland, K. J.; Moore, K. E. δ-Opioid Receptor-Mediated Regulation of Central Dopaminergic Neurons in the Rat. Eur. J. Pharmacol. 1993, 249, 107-112.
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 2046-2050
    • Spanagel, R.1    Herz, A.2    Shippenberg, T.S.3
  • 16
    • 0027331080 scopus 로고
    • δ-Opioid Receptor-Mediated Regulation of Central Dopaminergic Neurons in the Rat
    • (b) Spanagel, R.; Herz, A.; Shippenberg, T. S. Opposing Tonically Active Endogenous Opioid Systems Modulate the Mesolimbic Dopaminergic Pathway. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2046-2050. Manzanares, J.; Durham, R. A.; Lookingland, K. J.; Moore, K. E. δ-Opioid Receptor-Mediated Regulation of Central Dopaminergic Neurons in the Rat. Eur. J. Pharmacol. 1993, 249, 107-112.
    • (1993) Eur. J. Pharmacol. , vol.249 , pp. 107-112
    • Manzanares, J.1    Durham, R.A.2    Lookingland, K.J.3    Moore, K.E.4
  • 17
    • 0023715894 scopus 로고
    • Direct Dependence Studies in Rats with Agents Selective for Different Types of Opioid Receptors
    • (a) Cowan, A.; Zhu, X. Z.; Mosberg, H. I.; Omnaas, J. R.; Porreca, F. Direct Dependence Studies in Rats with Agents Selective for Different Types of Opioid Receptors. J. Pharmacol. Exp. Ther. 1988, 246, 950-955.
    • (1988) J. Pharmacol. Exp. Ther. , vol.246 , pp. 950-955
    • Cowan, A.1    Zhu, X.Z.2    Mosberg, H.I.3    Omnaas, J.R.4    Porreca, F.5
  • 19
    • 0021255492 scopus 로고
    • Cerebral Delta Opioid Receptors Mediate Analgesia but Not the Intestinal Motility Effects of Intracerebroventriculary Administered Opioids
    • (c) Galligan, J. J.; Mosberg, H. I.; Hurst, R.; Hruby, V. J.; Burks, T. F. Cerebral Delta Opioid Receptors Mediate Analgesia but Not the Intestinal Motility Effects of Intracerebroventriculary Administered Opioids. J. Pharmacol. Exp. Ther. 1984, 229, 641-648.
    • (1984) J. Pharmacol. Exp. Ther. , vol.229 , pp. 641-648
    • Galligan, J.J.1    Mosberg, H.I.2    Hurst, R.3    Hruby, V.J.4    Burks, T.F.5
  • 20
    • 0027462309 scopus 로고
    • Molecular Alterations in the Neostriatum of Human Cocaine Addicts
    • Hurd, Y. S.; Herkenham, M. Molecular Alterations in the Neostriatum of Human Cocaine Addicts. Synapse 1993, 13, 357-369.
    • (1993) Synapse , vol.13 , pp. 357-369
    • Hurd, Y.S.1    Herkenham, M.2
  • 22
    • 0005773734 scopus 로고
    • Cocaine Interactions with the Endogenous Opioid System
    • Hammer, R. P., Jr., Eds.; CRC Press: Boca Raton; FL
    • (b) Unterwald, E. M. Cocaine Interactions with the Endogenous Opioid System. In The Neurobiology of Cocaine: Cellular and Molecular Mechanisms; Hammer, R. P., Jr., Eds.; CRC Press: Boca Raton; FL, 1995; pp 145-162.
    • (1995) The Neurobiology of Cocaine: Cellular and Molecular Mechanisms , pp. 145-162
    • Unterwald, E.M.1
  • 24
    • 0027531763 scopus 로고
    • Naltrindole, an Opioid Delta Receptor Antagonist, Blocks Cocaine-Induced Facilitation of Responding for Rewarding Brain Stimulation
    • Reid, L. D.; Hubbell, C. L.; Glaccum, M. B.; Bilsky, E. J.; Portoghese, P. S.; Porreca, F. Naltrindole, an Opioid Delta Receptor Antagonist, Blocks Cocaine-Induced Facilitation of Responding for Rewarding Brain Stimulation. Life Sci. 1993, 52, PL 67-71.
    • (1993) Life Sci. , vol.52
    • Reid, L.D.1    Hubbell, C.L.2    Glaccum, M.B.3    Bilsky, E.J.4    Portoghese, P.S.5    Porreca, F.6
  • 25
    • 0028979171 scopus 로고
    • The δ-Opioid Receptor Antagonist Naltrindole Prevents Sensitization to the Conditioned Rewarding Effects of Cocaine
    • Shippenberg, T. S.; Heidbreder, C. The δ-Opioid Receptor Antagonist Naltrindole Prevents Sensitization to the Conditioned Rewarding Effects of Cocaine. Eur. J. Pharmacol. 1995, 280, 55-61.
    • (1995) Eur. J. Pharmacol. , vol.280 , pp. 55-61
    • Shippenberg, T.S.1    Heidbreder, C.2
  • 27
    • 0027385389 scopus 로고
    • A Novel, Potent and Selective Nonpeptidic Delta Opioid Receptor Agonist BW373U86
    • (a) Chang, K.-J.; Rigdon, G. C.; Howard, J. L.; McNutt, R. W. A Novel, Potent and Selective Nonpeptidic Delta Opioid Receptor Agonist BW373U86. J. Pharmacol. Exp. Ther. 1993, 267, 852-857.
    • (1993) J. Pharmacol. Exp. Ther. , vol.267 , pp. 852-857
    • Chang, K.-J.1    Rigdon, G.C.2    Howard, J.L.3    McNutt, R.W.4
  • 29
    • 0027495924 scopus 로고
    • Discriminative Stimulus Effects of BW373U86: A Nonpeptide Ligand with Selectivity for Delta Opioid Receptors
    • (c) Comer, S. D.; McNutt, R. W.; Chang, K.-J.; de Costa, B. R.; Mosberg, H. I.; Woods, J. H. Discriminative Stimulus Effects of BW373U86: A Nonpeptide Ligand with Selectivity for Delta Opioid Receptors. J. Pharmacol. Exp. Ther. 1993, 267, 866-874.
    • (1993) J. Pharmacol. Exp. Ther. , vol.267 , pp. 866-874
    • Comer, S.D.1    McNutt, R.W.2    Chang, K.-J.3    De Costa, B.R.4    Mosberg, H.I.5    Woods, J.H.6
  • 30
    • 0027485983 scopus 로고
    • A Nonpeptidic Delta Opioid Receptor Agonist, BW373U86, Attenuates the Development and Expression of Morphine Abstinence Precipitated by Naloxone in the Rat
    • (c) Lee, P. H. K.; McNutt, R. W.; Chang, K.-J. A Nonpeptidic Delta Opioid Receptor Agonist, BW373U86, Attenuates the Development and Expression of Morphine Abstinence Precipitated by Naloxone in the Rat. J. Pharmacol. Exp. Ther. 1993, 267, 883-887.
    • (1993) J. Pharmacol. Exp. Ther. , vol.267 , pp. 883-887
    • Lee, P.H.K.1    McNutt, R.W.2    Chang, K.-J.3
  • 32
    • 0027487230 scopus 로고
    • A Novel Delta Opioid Agonist, BW373U86, in Squirrel Monkeys Responding under a Schedule of Shock Titration
    • (e) Dykstra, L. A.; Schoenbaum, G. M.; Yarbrough, J.; McNutt, R.; Chang, K.-J. A Novel Delta Opioid Agonist, BW373U86, in Squirrel Monkeys Responding Under a Schedule of Shock Titration. J. Pharmacol. Exp. Ther. 1993, 267, 875-882.
    • (1993) J. Pharmacol. Exp. Ther. , vol.267 , pp. 875-882
    • Dykstra, L.A.1    Schoenbaum, G.M.2    Yarbrough, J.3    McNutt, R.4    Chang, K.-J.5
  • 33
    • 19244379844 scopus 로고
    • Probes for Narcotic Receptor Mediated Phenomena. 19. Synthesis of (+)-4-[(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3- methoxybenzyl]-N,N-diethylbenzamide (SNC 80): A Highly Selective, Nonpeptide δ Opioid Receptor Agonist
    • Calderon, S. N.; Rothman, R. B.; Porreca, F.; Flippen-Anderson, J. L.; McNutt, R. W.; Xu, H.; Smith, L. E.; Bilsky, E. J.; Davis, P.; Rice, K. C. Probes for Narcotic Receptor Mediated Phenomena. 19. Synthesis of (+)-4-[(αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3- methoxybenzyl]-N,N-diethylbenzamide (SNC 80): A Highly Selective, Nonpeptide δ Opioid Receptor Agonist. J. Med. Chem. 1994, 37, 2125-2128.
    • (1994) J. Med. Chem. , vol.37 , pp. 2125-2128
    • Calderon, S.N.1    Rothman, R.B.2    Porreca, F.3    Flippen-Anderson, J.L.4    McNutt, R.W.5    Xu, H.6    Smith, L.E.7    Bilsky, E.J.8    Davis, P.9    Rice, K.C.10
  • 34
    • 0023025052 scopus 로고
    • Stereochemistry: A Source of Problems in Medicinal Chemistry
    • Ariens, E. J. Stereochemistry: A Source of Problems in Medicinal Chemistry. Med. Res. Rev. 1986, 6, 451-466.
    • (1986) Med. Res. Rev. , vol.6 , pp. 451-466
    • Ariens, E.J.1
  • 36
    • 0343678156 scopus 로고
    • Benzimidazol-Derivate und Verwandte Heterocyclen III Synthese von 1-Aminoalkyl-2-benzyl-nitro-benzimidazolen
    • Hunger, A.; Kebrle, J.; Rossi, A.; Hoffman, A. Benzimidazol-Derivate und Verwandte Heterocyclen III) Synthese von 1-Aminoalkyl-2-benzyl-nitro-benzimidazolen. Helv. Chim. Acta 1960, 43, 1032-1046.
    • (1960) Helv. Chim. Acta , vol.43 , pp. 1032-1046
    • Hunger, A.1    Kebrle, J.2    Rossi, A.3    Hoffman, A.4
  • 37
    • 0014516814 scopus 로고
    • Piperazine Compounds. II. Synthesis of 1-Piperazinylbarbituric acid Derivatives and Some of their Pharmacological Activities
    • Ikeda, Y.; Nitta, Y.; Yamada, K. Piperazine Compounds. II. Synthesis of 1-Piperazinylbarbituric acid Derivatives and Some of their Pharmacological Activities. Yakagaku Zasshi 1969, 89, 669-676.
    • (1969) Yakagaku Zasshi , vol.89 , pp. 669-676
    • Ikeda, Y.1    Nitta, Y.2    Yamada, K.3
  • 38
    • 0037740043 scopus 로고
    • Analgesic Diarylmethylpiperazines and Piperidines
    • International Patent Application WO 9315062, August 5, 1993
    • (a) Chang, K.-J.; Boswell, G. E.; Bubacz, D. G.; Collins, M. A.; Davis, A. O.; McNutt, R. W. Analgesic Diarylmethylpiperazines and Piperidines. International Patent Application WO 9315062, August 5, 1993; Chem. Abstr. 1994, 121, 83367.
    • (1994) Chem. Abstr. , vol.121 , pp. 83367
    • Chang, K.-J.1    Boswell, G.E.2    Bubacz, D.G.3    Collins, M.A.4    Davis, A.O.5    McNutt, R.W.6
  • 39
    • 0029068024 scopus 로고
    • An Efficient Synthesis of the Benzhydrylpiperazine Delta Opioid Agonist (+)-BW373U86
    • (b) Bishop, M. J.; McNutt, R. W. An Efficient Synthesis of the Benzhydrylpiperazine Delta Opioid Agonist (+)-BW373U86. Bioorg. Med. Chem. Lett. 1995, 5, 1311-1314.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 1311-1314
    • Bishop, M.J.1    McNutt, R.W.2
  • 40
    • 0023901413 scopus 로고
    • Studies on the Total Synthesis of Bouvardin and Deoxybouvardin: Cyclic Hexapeptide Cyclization Studies and Preparation of Key Partial Structures
    • Boger, D. L.; Yohannes, D. Studies on the Total Synthesis of Bouvardin and Deoxybouvardin: Cyclic Hexapeptide Cyclization Studies and Preparation of Key Partial Structures. J. Org. Chem. 1988, 53, 487-499.
    • (1988) J. Org. Chem. , vol.53 , pp. 487-499
    • Boger, D.L.1    Yohannes, D.2
  • 41
    • 0000763544 scopus 로고
    • Chemoselective N-Ethylation of Boc Amino Acids Without Racemization
    • Hansen, D. W., Jr.; Pilipauskas, D. Chemoselective N-Ethylation of Boc Amino Acids Without Racemization. J. Org. Chem. 1985, 50, 945-950.
    • (1985) J. Org. Chem. , vol.50 , pp. 945-950
    • Hansen Jr., D.W.1    Pilipauskas, D.2
  • 42
    • 0011287386 scopus 로고
    • An Improved Synthesis of (R)- and (S)-2-Methylpiperazine
    • Kiely, J. S.; Priebe, S. R. An Improved Synthesis of (R)- and (S)-2-Methylpiperazine. Org. Prep. Proced. Int. 1990, 22, 761-764.
    • (1990) Org. Prep. Proced. Int. , vol.22 , pp. 761-764
    • Kiely, J.S.1    Priebe, S.R.2
  • 43
    • 33947302252 scopus 로고
    • A Simple Route to Sterically Pure Diketopiperazines
    • Nitecki, D. E.; Halpern, B.; Westley, J. W. A Simple Route to Sterically Pure Diketopiperazines. J. Org. Chem. 1968, 33, 864-866.
    • (1968) J. Org. Chem. , vol.33 , pp. 864-866
    • Nitecki, D.E.1    Halpern, B.2    Westley, J.W.3
  • 44
    • 0025729102 scopus 로고
    • RTI-4614-4: An Analog of (+)-Cis-3-methylfentanyl with a 27,000-fold Binding Selectivity for Mu Versus Delta Binding Sites
    • Rothman, R. B.; Xu, H.; Seggel, M.; Jacobson, A. E.; Rice, K. C.; Brine, G. A.; Carroll, F. I. RTI-4614-4: An Analog of (+)-Cis-3-methylfentanyl with a 27,000-fold Binding Selectivity for Mu Versus Delta Binding Sites. Life Sci. 1991, 48; PL111-PL116.
    • (1991) Life Sci. , vol.48
    • Rothman, R.B.1    Xu, H.2    Seggel, M.3    Jacobson, A.E.4    Rice, K.C.5    Brine, G.A.6    Carroll, F.I.7
  • 45
    • 0027102462 scopus 로고
    • Interaction of Opioid Peptides and Other Drugs with Multiple δncx Binding Sites in Rat Brain: Further Evidence for Heterogenity
    • Xu, H.; Partilla, J. S.; de Costa, B. R.; Rice, K. C.; Rothman, R. B. Interaction of Opioid Peptides and Other Drugs with Multiple δncx Binding Sites in Rat Brain: Further Evidence for Heterogenity. Peptides 1992, 13, 1207-1213.
    • (1992) Peptides , vol.13 , pp. 1207-1213
    • Xu, H.1    Partilla, J.S.2    De Costa, B.R.3    Rice, K.C.4    Rothman, R.B.5
  • 47
    • 14444283806 scopus 로고    scopus 로고
    • Synthesis, Binding and Bioassay Studies of SNC 80 and Related Nonpeptidic Delta Opioid Receptor Agonists
    • Harris, L. S., Ed.; NIDA Research Monograph: Washington, DC, in press
    • Calderon, S. N.; Flippen-Anderson, J.; Xu, H.; Becketts, K. M.; Rothman, R. B.; Davis, P.; Porreca, F.; Rice, K. C. Synthesis, Binding and Bioassay Studies of SNC 80 and Related Nonpeptidic Delta Opioid Receptor Agonists. Problems of Drug Dependence, 1995; Harris, L. S., Ed.; NIDA Research Monograph: Washington, DC, 1996, in press.
    • (1996) Problems of Drug Dependence, 1995
    • Calderon, S.N.1    Flippen-Anderson, J.2    Xu, H.3    Becketts, K.M.4    Rothman, R.B.5    Davis, P.6    Porreca, F.7    Rice, K.C.8
  • 48
    • 0027485085 scopus 로고
    • In Vitro Potency, Affinity and Agonist Efficacy of Highly Selective Delta Opioid Receptor Ligands
    • Proceedings of the College on Problems of Drug Dependence
    • Kramer, T. H.; Davis, P.; Hruby, V. J.; Burks, T. F.; Porreca, F. In Vitro Potency, Affinity and Agonist Efficacy of Highly Selective Delta Opioid Receptor Ligands. J. Pharmacol. Exp. Ther. 1993, 266, 577-584. Proceedings of the College on Problems of Drug Dependence, 1996.
    • (1993) J. Pharmacol. Exp. Ther. , vol.266 , pp. 577-584
    • Kramer, T.H.1    Davis, P.2    Hruby, V.J.3    Burks, T.F.4    Porreca, F.5
  • 49
    • 0021360245 scopus 로고
    • ICI 174,864: A Highly Selective Antagonist for the Opioid δ Receptor
    • Cotton, R.; Gills, M. G.; Miller, L.; Shaw, J. S.; Timms, D. ICI 174,864: A Highly Selective Antagonist for the Opioid δ Receptor. Eur. J. Pharmacol. 1984, 97, 331-332.
    • (1984) Eur. J. Pharmacol. , vol.97 , pp. 331-332
    • Cotton, R.1    Gills, M.G.2    Miller, L.3    Shaw, J.S.4    Timms, D.5
  • 51
    • 0002789284 scopus 로고
    • Synthesis of Non-Peptidic Delta Opioid Agonists and their Structure Activity Relationships
    • (a) Nagase, H.; Wakita, H.; Kawei, K.; Endoh, T.; Matsuura, H.; Tanaka, C.; Takezawa, Y. Synthesis of Non-Peptidic Delta Opioid Agonists and their Structure Activity Relationships. Jpn. J. Pharmacol. 1994, 64, Suppl. I, 35P.
    • (1994) Jpn. J. Pharmacol. , vol.64 , Issue.1 SUPPL.
    • Nagase, H.1    Wakita, H.2    Kawei, K.3    Endoh, T.4    Matsuura, H.5    Tanaka, C.6    Takezawa, Y.7
  • 52
    • 0028967685 scopus 로고
    • Antinociceptive Effects of the Selective Non-peptidic δ- Opioid Receptor Agonist TAN-67 in Diabetic Mice
    • (b) Kamei, J.; Saitoh, A.; Oshsawa, M.; Suzuki, T.; Misawa, M.; Nagase, H.; Kasuya, Y. Antinociceptive Effects of the Selective Non-peptidic δ-Opioid Receptor Agonist TAN-67 in Diabetic Mice. Eur. J. Pharmacol. 1995, 276, 131-135.
    • (1995) Eur. J. Pharmacol. , vol.276 , pp. 131-135
    • Kamei, J.1    Saitoh, A.2    Oshsawa, M.3    Suzuki, T.4    Misawa, M.5    Nagase, H.6    Kasuya, Y.7
  • 53
    • 5244225688 scopus 로고
    • Preparation of Hydroindoloisoquinoline Derivatives and Analogs as δ-Receptor Agonists
    • International Patent Application WO 9301186, January 21, 1993
    • (c) Colle, R.; Vecchietti, V.; Dondio, G.; Ronzoni, S. Preparation of Hydroindoloisoquinoline Derivatives and Analogs as δ-Receptor Agonists. International Patent Application WO 9301186, January 21, 1993; Chem. Abstr. 1993, 119, 8795.
    • (1993) Chem. Abstr. , vol.119 , pp. 8795
    • Colle, R.1    Vecchietti, V.2    Dondio, G.3    Ronzoni, S.4
  • 54
    • 0004150157 scopus 로고
    • Siemens Analytical X-ray Instruments, Inc.: Madison, WI
    • Sheldrick, G. M. SHELXTL-Plus, Release 4.2; Siemens Analytical X-ray Instruments, Inc.: Madison, WI, 1992.
    • (1992) SHELXTL-Plus, Release 4.2
    • Sheldrick, G.M.1
  • 56
    • 14444280551 scopus 로고    scopus 로고
    • Atomic coordinates may be obtained from the Cambridge Crystallographic Data Centre (Cambridge University Chemical Laboratory, Cambridge CB2 1EW, U.K.)
    • Atomic coordinates may be obtained from the Cambridge Crystallographic Data Centre (Cambridge University Chemical Laboratory, Cambridge CB2 1EW, U.K.).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.