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Volumn 42, Issue 26, 1999, Pages 5455-5463

Probes for narcotic receptor mediated phenomena. 26. Synthesis and biological evaluation of diarylmethylpiperazines and diarylmethylpiperidines as novel, nonpeptidic δ opioid receptor ligands

Author keywords

[No Author keywords available]

Indexed keywords

4 (1 PIPERAZINYLBENZYL) N,N DIETHYLBENZAMIDE; 4 [(4 ALLYL 1 PIPERAZINYL) 3 METHOXYBENZYL] N,N DIETHYLBENZAMIDE; 4 [(4 BENZYL 1 PIPERAZINYL)BENZYL] N,N DIETHYLBENZAMIDE; 4 [(4 PIPERIDINYLIDENE) 3 METHOXYBENZYL] N,N DIETHYLBENZAMIDE; DELTA OPIATE RECEPTOR; DELTA OPIATE RECEPTOR AGONIST; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; UNCLASSIFIED DRUG;

EID: 17544394335     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9903895     Document Type: Article
Times cited : (22)

References (40)
  • 1
    • 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 (SNC80): 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 (SNC80): 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
  • 2
    • 14444274551 scopus 로고    scopus 로고
    • 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
    • Calderon, S. N.; Rice, K. C.; Rothman, R. B.; Porreca, F.; Flippen-Anderson, J. L.; Kayakiri, H.; Xu, H.; Becketts, K.; Smith, L. E.; Bilsky, E. J.; Davis, P.; Horvath, R. 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. J. Med. Chem. 1997, 40, 695-704.
    • (1997) J. Med. Chem. , vol.40 , pp. 695-704
    • Calderon, S.N.1    Rice, K.C.2    Rothman, R.B.3    Porreca, F.4    Flippen-Anderson, J.L.5    Kayakiri, H.6    Xu, H.7    Becketts, K.8    Smith, L.E.9    Bilsky, E.J.10    Davis, P.11    Horvath, R.12
  • 5
    • 0017735536 scopus 로고
    • Endogenous opioid peptides: Multiple agonists and receptors
    • 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
  • 6
    • 0342381829 scopus 로고
    • The multiplicity of opioid receptors and their functional significance
    • Mulschler, E., Winterfeldt, E., Eds.; VCH Velagsgesellschaft: Berlin
    • 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; Mulschler, E., Winterfeldt, E., Eds.; VCH Velagsgesellschaft: Berlin, 1987; pp 337-350.
    • (1987) Trends in Medicinal Chemistry: Proceedings of the 9th International Symposium on Medicinal Chemistry , pp. 337-350
    • Herz, A.1
  • 7
    • 0025072676 scopus 로고
    • Selective modulation of morphine antinociception, but not development of tolerance, by δ receptor antagonists
    • Jiang, Q.; Mosberg, H. I.; Porreca, F. Selective Modulation of Morphine Antinociception, but Not Development of Tolerance, by δ Receptor Antagonists. 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
  • 8
    • 0026550559 scopus 로고
    • Antinociceptive interactions of opioid delta receptor agonists with morphine in mice: Supra- and sub-additivity
    • Horan, P.; Tallarida, R. J.; Haaseth, R. C.; Matsunaga, T. O.; Hruby, V. I.; 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.I.5    Porreca, F.6
  • 12
    • 0027385389 scopus 로고
    • Novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86
    • 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.A.4
  • 15
    • 0004787283 scopus 로고    scopus 로고
    • BW373U86: A non-peptide systemically-active δ opioid agonist
    • Negus, S. S.; Picker, M. J. BW373U86: A Non-Peptide Systemically-Active δ Opioid Agonist. CNS Drug Rev. 1996, 2, 52-74.
    • (1996) CNS Drug Rev. , vol.2 , pp. 52-74
    • Negus, S.S.1    Picker, M.J.2
  • 16
    • 0000813864 scopus 로고    scopus 로고
    • Convulsive behavior of nonpeptide δ-opioid ligands: Comparison of SNC80 and BW373U86 in mice
    • Hong, E. J.; Rice, K. C.; Calderon, S.; Woods, J. H.; Trayuor, J. R. Convulsive Behavior of Nonpeptide δ-Opioid Ligands: Comparison of SNC80 and BW373U86 in Mice. Analgesia 1998, 3, 269-276.
    • (1998) Analgesia , vol.3 , pp. 269-276
    • Hong, E.J.1    Rice, K.C.2    Calderon, S.3    Woods, J.H.4    Trayuor, J.R.5
  • 17
    • 0031817881 scopus 로고    scopus 로고
    • Behavioral effects of the delta-selective opioid agonist SNC80 and related compounds in Rhesus monkeys
    • Negus, S. S.; Gatch, M. B.; Mello, N. K.; Zhang, X. Y.; Rice, K. Behavioral Effects of the Delta-Selective Opioid Agonist SNC80 and Related Compounds in Rhesus Monkeys. J. Pharmacol. Exp. Ther. 1998, 286, 362-375.
    • (1998) J. Pharmacol. Exp. Ther. , vol.286 , pp. 362-375
    • Negus, S.S.1    Gatch, M.B.2    Mello, N.K.3    Zhang, X.Y.4    Rice, K.5
  • 18
    • 0027444691 scopus 로고
    • A single residue, aspartic acid 95, in the δ opioid receptor specifies selective high affinity agonist binding
    • Kong, H.; Raynor, K.; Yasuda, K.; Moe, S. T.; Portoghese, P. S.; Bell, G. I.; Reisine, T. A Single Residue, Aspartic Acid 95, in the δ Opioid Receptor Specifies Selective High Affinity Agonist Binding. J. Biol. Chem. 1993, 268, 23055-23058.
    • (1993) J. Biol. Chem. , vol.268 , pp. 23055-23058
    • Kong, H.1    Raynor, K.2    Yasuda, K.3    Moe, S.T.4    Portoghese, P.S.5    Bell, G.I.6    Reisine, T.7
  • 19
    • 0030641585 scopus 로고    scopus 로고
    • Development of a common 3D pharmacophore for δ opioid recognition from peptides and nonpeptidic using a novel computer program
    • Huang, P.; Kim, S.; Loew, G. Development of a Common 3D Pharmacophore for δ Opioid Recognition from Peptides and Nonpeptidic Using a Novel Computer Program. J. Comput.-Aided Mol. Des. 1997, 11, 21-28.
    • (1997) J. Comput.-Aided Mol. Des. , vol.11 , pp. 21-28
    • Huang, P.1    Kim, S.2    Loew, G.3
  • 20
    • 0030040907 scopus 로고    scopus 로고
    • The conserved aspartate residue in the third putative transmembrane domain of the δ-Opioid receptor is not the anionic counterpart for cationic opiate binding but is a constituent of the receptor binding site
    • Befort, K.; Tabbara, L.; Bausch, S.; Chavkin, C.; Evans, C.; Kieffer, B. The Conserved Aspartate Residue in the Third Putative Transmembrane Domain of the δ-Opioid Receptor is not the Anionic Counterpart for Cationic Opiate Binding but is a Constituent of the Receptor Binding Site. Mol. Pharm. 1996, 49, 216-223.
    • (1996) Mol. Pharm. , vol.49 , pp. 216-223
    • Befort, K.1    Tabbara, L.2    Bausch, S.3    Chavkin, C.4    Evans, C.5    Kieffer, B.6
  • 21
    • 0000739376 scopus 로고    scopus 로고
    • Computer modeling of δ opioid receptor and interaction with ligands
    • Poda, G.; Maigret, B. Computer Modeling of δ Opioid Receptor and Interaction with Ligands. Lett. Pept. Sci. 1998, 5, 193-197.
    • (1998) Lett. Pept. Sci. , vol.5 , pp. 193-197
    • Poda, G.1    Maigret, B.2
  • 23
    • 0033519307 scopus 로고    scopus 로고
    • Synthesis of novel analogues of the delta opioid ligand SNC-80 using REM resin
    • Cottney, J.; Rankovic, Z.; Morphy, J. R. Synthesis of Novel Analogues of the Delta Opioid Ligand SNC-80 Using REM Resin. Bioorg. Med. Chem. Lett. 1999, 9, 1323-1328.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 1323-1328
    • Cottney, J.1    Rankovic, Z.2    Morphy, J.R.3
  • 25
    • 0032573617 scopus 로고    scopus 로고
    • Asymmetric synthesis of diarylmethylamines: preparation of selective opioid delta receptor ligands
    • Delorme, D.; Berthelette, C.; Lavoie, R.; Roberts, E. Asymmetric Synthesis of Diarylmethylamines: Preparation of Selective Opioid Delta Receptor Ligands. Tetrahedron: Asymmetry 1998, 9, 3963-3966.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3963-3966
    • Delorme, D.1    Berthelette, C.2    Lavoie, R.3    Roberts, E.4
  • 29
    • 0018514611 scopus 로고
    • Studies of psychotropic agent v. synthesis of 1-substituted spiro[dibenz[b,f]oxepin-11,4′-piperidine]-10-(11H)-one and related compound
    • Nagai, Y.; Uno, H. Studies of Psychotropic Agent V. Synthesis of 1-Substituted Spiro[dibenz[b,f]oxepin-11,4′-piperidine]-10-(11H)-one and Related Compound. Chem. Pharm. Bull. 1979, 27, 2056-2064.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 2056-2064
    • Nagai, Y.1    Uno, H.2
  • 31
    • 0346618937 scopus 로고
    • Crossed coupling of functionalized ketones by low valent titanium (the McMurry reaction): A new stereoselective synthesis of tamoxifen
    • Coe, P. L.; Scriven, C. E. Crossed Coupling of Functionalized Ketones by Low Valent Titanium (The McMurry Reaction): A New Stereoselective Synthesis of Tamoxifen. J. Chem. Soc., Perkin Trans. 1 1986, 475-477.
    • (1986) J. Chem. Soc., Perkin Trans. 1 , pp. 475-477
    • Coe, P.L.1    Scriven, C.E.2
  • 32
    • 0029068024 scopus 로고
    • An efficient synthesis of the benzhydrylpiperazine delta opioid agonist (+)-BW373U86
    • 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
  • 33
    • 0008432385 scopus 로고    scopus 로고
    • An improved synthesis of SNC80, a highly selective delta opioid receptor agonist
    • Harris, L. S., Ed.; NIDA Research Monograph 174: Washington, DC
    • Zhang, X.; Calderon, S. N.; Rice, K. C. An Improved Synthesis of SNC80, A Highly Selective Delta Opioid Receptor Agonist. In Problems of Drug Dependence 1996; Harris, L. S., Ed.; NIDA Research Monograph 174: Washington, DC, 1996; p 101.
    • (1996) Problems of Drug Dependence 1996 , pp. 101
    • Zhang, X.1    Calderon, S.N.2    Rice, K.C.3
  • 34
    • 0025729102 scopus 로고
    • An analogue 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. An Analogue 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
  • 36
    • 0025256967 scopus 로고
    • Interaction of endogenous opioid peptides and other drugs with four kappa opioid binding sites in guinea pig brain
    • Rothman, R. B.; de Costa, B. R.; Bykoe, V.; Jacobson, A. E.; Rice, K. C.; Brady, L. S. Interaction of Endogenous Opioid Peptides and Other Drugs with Four Kappa Opioid Binding Sites in Guinea Pig Brain. Peptides 1990, 11, 311-331.
    • (1990) Peptides , vol.11 , pp. 311-331
    • Rothman, R.B.1    De Costa, B.R.2    Bykoe, V.3    Jacobson, A.E.4    Rice, K.C.5    Brady, L.S.6
  • 37
    • 0032417920 scopus 로고    scopus 로고
    • Synthesis, in vitro, and in vivo activity of N-p-substituted-Benzyl-(-) and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N-norketobemidones, and (-)-N-Nor-4,5-epoxymorphinans
    • May, E. L.; Jacobson, A. E.; Mattson, M. V.; Coop, A.; Aceto, M. D.; Bowman, E. R.; Traynor, J. R.; Woods, J. H.; Harris, L. S. Synthesis, In Vitro, and In Vivo Activity of N-p-Substituted-Benzyl-(-) and (+)-N-Normetazocines, (-)- and (+)-N-Normorphinans, N-Norketobemidones, and (-)-N-Nor-4,5-Epoxymorphinans. Med. Chem. Res. 1998, 8, 311-321.
    • (1998) Med. Chem. Res. , vol.8 , pp. 311-321
    • May, E.L.1    Jacobson, A.E.2    Mattson, M.V.3    Coop, A.4    Aceto, M.D.5    Bowman, E.R.6    Traynor, J.R.7    Woods, J.H.8    Harris, L.S.9
  • 38
    • 0033535142 scopus 로고    scopus 로고
    • The LMC delta opioid recognition pharmacophore. Comparison of SNC80 and oxymorphindole
    • Coop, A.; Jacobson, A. E. The LMC Delta Opioid Recognition Pharmacophore. Comparison of SNC80 and Oxymorphindole. Bioorg. Med. Chem. Lett. 1999, 9, 357-362.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 357-362
    • Coop, A.1    Jacobson, A.E.2
  • 39
    • 0027485085 scopus 로고
    • In vitro potency, affinity and agonist efficacy of highly selective delta opioid receptor ligands
    • 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.
    • (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


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