Nonpeptidic delta (δ) opioid agonists and antagonists of the diarylmethylpiperazine class: What have we learned?

Topics in Current Chemistry

Volumn 299, Issue , 2011, Pages 121-140

  Calderon, Silvia N ^a  

^a CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

Author keywords

Agonists; Antagonists; Diphenylmethylpiperazines; Nonpeptidic delta ligands; SNC 80

Indexed keywords

DELTA OPIATE RECEPTOR; PIPERAZINE DERIVATIVE;

ANIMAL; ARTICLE; DRUG ANTAGONISM; DRUG POTENTIATION; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; HUMANS; PIPERAZINES; RECEPTORS, OPIOID, DELTA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79551469677     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2010_83     Document Type: Article

References (61)

1. Pasternak GW (1993) Pharmacological mechanisms of opioid analgesics. Clin Neuropharma-col 16:1-18
2. Quock RM, Burkey TH, Varga E et al (1999) The delta-opioid receptor: molecular pharmacology, signal transduction, and the determination of drug efficacy. Pharmacol Rev 51:503-532
3. Kieffer BL, Befort K, Gavriaux-Ruff C, Hirth CG (1992) The delta-opioid receptor: isolation of a cDNA by expression cloning and pharmacological characterization. Proc Natl Acad Sci USA 89:12048-12052
4. Evans CJ, Keith DE, Morrison H et al (1992) Cloning of a delta opioid receptor by functional expression. Science 258:1952-1955
5. Mansson E, Bare L, Yang D (1994) Isolation of a human kappa opioid receptor cDNA from placenta. Biochem Biophys Res Commun 202:1431-1437
6. Raynor K, Kong H, Chen Y et al (1994) Pharmacological characterization of the cloned kappa-, delta-, and mu-opioid receptors. Mol Pharmacol 45:330-334
7. Brandt MR, Furness MS, Mello NK et al (2001) Antinociceptive effects of delta opioid agonists in rhesus monkeys: effects on chemically induced thermal hypersensitivity. J Pharmacol Exp Ther 296:939-946
8. Mika J, Przewlocki R, Przewlocka B (2001) The role of delta opioid receptor subtypes in neuropathic pain. Eur J Pharmacol 415:31-37
9. Craft RM, Henley SR, Haaseth RC et al (1995) Opioid antinociception in a rat model of visceral pain: systemic versus local drug administration. J Pharmacol Exp Ther 275:1535-1542
10. Broom DC, Jutkiewicz EM, Rice KC et al (2002) Behavioral effects of d-opioid receptor agonists: potential antidepressants? Jpn J Pharmacol 90:1-6
11. Jutkiewicz EM (2006) The antidepressant-like effects of delta-opioid receptor agonists. Mol Interv 6:162-169
12. Hallet PJ, Brotchie JM (2007) Striatal delta opioid receptor binding in experimental models of Parkinson's disease and dyskinesia. Mov Disord 22:28-40
13. Shippenberg TS, LeFevour A, Chefer VI (2008) Targeting endogenous mu- and delta-opioid receptor systems for the treatment of drug addiction. CNS Neurol Disord Drug Targets 7:442-453
14. Corazziari E (1999) Role of opioid ligands in the irritable syndrome. Can J Gastroenterol 13(Suppl A):71A-75A
15. Rapaka RS, Porreca F (1991) Development of delta opioid peptides as non-addicting analgesics. Pharm Res 8:1-8
16. Galligan JJ, Mosberg HI, Hurst R et al (1984) Cerebral delta opioid receptors mediate analgesia but not the intestinal motility effects of intracerebroventricularly administered opioids. J Pharmacol Exp Ther 229:641-648
17. Reisine T, Pasternak G (1996) Opioid analgesics and antagonists. In: Hardman JG, Limbird LE, Molinoff PB, Ruddon RW, Gila AG (ed)s) Goodman & Gilman's the pharmacological basis of therapeutics, 9th edn. McGraw-Hill, New York
18. Heyl DL, Schullery SE (1997) Developments in the structure-activity relationships for the delta-selective opioid peptides of amphibian skin. Curr Med Chem 4:117-150
19. Egleton RD, Davis TP (1997) Bioavailability and transport of peptides and peptide drugs into the brain. Peptides 18:1431-1439
20. Portoghese PS, Sultana M, Nagase H (1988) Application of message-address concept in the design of highly potent and selective non-peptide d opioid receptor antagonists. J Med Chem 31:281-282
21. Schwyzer R (1977) ACTH: a short introductory review. Ann NY Acad Sci 297:3-26
22. Lee PHK, McNutt RW, Chang K-J. In: Abstracts of the 1992 college on problems of drug dependence- international narcotics research conference, Abstract 34
23. Chang KJ, Rigdon GC, Howard JL, McNutt RW (1993) A novel, potent and selective nonpeptidic delta opioid receptor agonist BW373U86. J Pharmacol Exp Ther 267:852-857
24. Calderon SN, Rothman RB, Porreca F et al (1994) Probes for narcotic receptor mediated phenomena. 19. Synthesis of (\+)-4-[(aR)-a-((2 S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC 80): a highly selective, nonpeptide delta opioid receptor agonist. J Med Chem 37:2125-2128
25. Portoghese PS, Moe ST, Takemori AE (1993) A selective d1 opioid receptor agonist derivative from oxymorphone. Evidence for separate recognition sites for d1 opioid receptor agonists and antagonists. J Med Chem 36:2572-2574
26. Kamei J, Saitoh A, Ohsawa M et al (1995) Antinociceptive effects of the selective non-peptidic delta-opioid receptor agonist TAN-67 in diabetic mice. Eur J Pharmacol 276:131-135
27. Nagase H, Kawai K, Hayakawa J et al (1998) Rational drug design and synthesis of a highly selective nonpeptide d-opioid agonist, (4aS*,12aR*)-4a-(3-hydroxyphenyl)-2-methyl-1,2,3,44a,12, 12a-octahydropyrido[3,4-b]acridine (TAN-67). Chem Pharm Bull 46:1695-1702
28. Dondio G, Ronzoni S, Petrillo P (1997) Non-peptide delta opioid agonists and antagonists. Exp Opin Ther Pat 7:1075-1098
29. Dondio G, Ronzoni S, Petrillo P (1999) Non-peptide delta opioid agonists and antagonists (part II). Exp Opin Ther Pat 9:353-374
30. Dondio G, Ronzoni S, Eggleson DS et al (1997) Discovery of a novel class of substituted pyrrolooctahydroisoquinolines as potent and selective delta opioid agonists, based on an extension of the message-address concept. J Med Chem 40:3192-3198
31. Su YF, McNutt RW, Chang KJ (1998) Delta-opioid ligands reverse alfentanil-induced respiratory depression but not antinociception. J Pharmacol Exp Ther 287:815-823
32. Liras S, McHardy SF, Allen MP et al (2010) Biaryl piperidines as potent and selective delta opioid receptor ligands. Bioorg Med Chem Lett 20:503-507
33. Calderon SN, Coop A (2004) SNC 80 and related agonists. Curr Pharm Des 10:733-742
34. Chang K-J, Boswell GE, Bubacz DG, Collins MA, Davis AO, McNutt RW (1993) International Patent Application WO93/15062
35. Wild KD, McCormick J, Bilsky EJ et al (1993) Antinociceptive actions of BW373U86 in the mouse. J Pharmacol Exp Ther 267:858-865
36. Bilsky EJ, Calderon SN, Wang T et al (1995) SNC 80, a selective, nonpeptidic and systemi-cally active opioid delta agonist. J Pharmacol Exp Ther 273:359-366
37. Calderon SN, Rice KC, Rothman RB et al (1997) Probes for narcotic receptor mediated phenomena. 23. Synthesis, opioid receptor binding, and bioassay of the highly selective delta agonist (\+)-4-[(aR)-a-((2 S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC 80) and related novel nonpeptide delta opioid receptor ligands. J Med Chem 40:695-704
38. Katsura Y, Zhang X, Homma K et al (1997) Probes for narcotic receptor-mediated phenomena. 25. Synthesis and evaluation of N-alkyl-substituted (a-piperazinylbenzyl)benzamides as novel, highly selective delta opioid receptor agonists. J Med Chem 40:2936-2947
39. Bishop MJ, Garrido DM, Boswll GE et al (2003) 3-(aR)-a((2S,5R)-4-Allyl-2, 5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-alkyl-N-arylbenzamides: potent, non-peptidic agonists of both the m and d opioid receptors. J Med Chem 46:623-633
40. Middleton DS, Maw GN, Challenger C et al (2006) Highly potent and selective zwitterionic agonists of the delta-opioid receptor. Part 1. Bioorg Med Chem Lett 16:905-910
41. Zhang X, Rice KC, Calderon SN et al (1999) Probes for narcotic receptor mediated phenomena. 26. Synthesis and biological evaluation of diarylmethylpiperazines and diarylmethylpi-peridines as novel, nonpeptidic delta opioid receptor ligands. J Med Chem 42:5455-5463
42. Cottney J, Rankovic Z, Morphy JR (1999) Synthesis of novel analogues of the delta opioid ligand SNC-80 using REM resin. Bioorg Med Chem Lett 9:1323-1328
43. Barn DR, Bom A, Cottney J et al (1999) Synthesis of novel analogues of the delta opioid ligand SNC-80 using AlCl3-promoted aminolysis. Bioorg Med Chem Lett 9:1329-1334 (Pubitemid 29207456)
44. Delorme D, Berthelette C, Lavoie R, Roberts E (1998) Asymmetric synthesis of diarylmethy-lamines: preparation of selective opioid delta receptor ligands. Tetrahedron Asymmetry 9:3963-3966
45. Furness SC, Zhang X, Coop A et al (2000) Probes for narcotic receptor-mediated phenomena. 27. Synthesis and pharmacological evaluation of selective delta-opioid receptor agonists from 4-[(aR)-alpha-(2S,5R)-4- substituted-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N, N-diethylbenzamides and their enantiomers. J Med Chem 43:3193-3196
46. Pobleck N, Delorme D, Wei Z-Y et al (2000) New diarylmethylpiperazines as potent and selective nonpeptidic delta opioid receptor agonists with increased in vitro metabolic stability. J Med Chem 43:3878-3894
47. Liao S, Alfaro-Lopez J, Shenderovich MD et al (1998) De novo design, synthesis, and biological activities of high-affinity and selective non-peptide agonists of the delta-opioid receptor. J Med Chem 41:4767-4776
48. Alfaro-Lopez J, Okayama T, Hosohata K et al (1999) Exploring the structure-activity relationships of [1-(4-tert-butyl-3'-hydroxy)benzhydryl-4- benzylpiperazine] (SL-3111), a high-affinity and selective d-opioid receptor nonpeptide agonist ligand. J Med Chem 42:5359-5368
49. Wei Z-Y, Brown W, Takasaki B et al (2000) N,N-Diethyl-4-(phenylpiperidin- 4-ylidene-methyl)benzamide: a novel, exceptionally selective, potent delta opioid receptor agonist with oral bioavailability and its analogues. J Med Chem 43:3895-3905
50. Pelcman B, Roberts E (1998) International Patent Application WO 98/28270
51. Thomas JB, Herault XM, Rothman RB et al (1999) (+/-)-4-[(N-Allyl-cis-3- methyl-4-piperidinyl)phenylamino]-N,N-diethylbenzamide displays selective binding for the delta opioid receptor. Bioorg Med Chem Lett 9:3053-3056
52. Thomas JB, Atkinson RN, Herault XM et al (1999) Optically pure (-)-4-[(N-allyl-3-methyl-4-piperidinyl)phenyl-amino]-N,N-diethylbenzamide displays selective binding and full agonist activity for the delta opioid receptor. Bioorg Med Chem Lett 9:3347-3350
53. Thomas JB, Herault XM, Rothman RB et al (2001) Factors influencing agonist potency and selectivity for the opioid delta receptor are revealed in structure-activity relationship studies of the 4-[(N-substituted-4-piperidinyl) arylamino]-N,N-diethylbenzamides. J Med Chem 44:972-987
54. Boyd RE, Carson JR, Codd EE et al (2000) Synthesis and binding affinities of 4-diarylamino-tropanes, a new class of delta opioid agonists. Bioorg Med Chem Lett 10:1109-1111
55. Holl R, Jung B, Schepmann D et al (2009) Synthesis and pharmacological evaluation of SNC80 analogues with bridged piperazine ring. ChemMedChem 4:2111-2122
56. Bishop MJ, McNutt RW (1995) An efficient synthesis of the benzhydrylpiperazine delta opioid agonist (+)-BW373U86. Bioorg Med Chem Lett 5:1311-1314
57. Katritzky AR, Rachwal S, Rachwal B (1987) The chemistry of N-substituted benzotriazoles. Part 4. A novel and versatile method for the mono-N-alkylation of aromatic and heteroaro-matic amines. J Chem Soc Perkin Trans I:805-809
58. Katritzky AR, Yannakopoulou K, Lue P et al (1989) The chemistry of N-substituted benzotriazoles. Part 14. Novel routes to secondary and tertiary amines and N,N-disubstituted hydroxylamines. J Chem Soc Perkin Trans I:225-233
59. Corey EJ, Helal CJ (1996) Catalytic enantioselective synthesis of the second generation histamine agonist cetirizine hydrochloride. Tetrahedron Lett 37:4837-4840
60. Janetka JW, Furness MS, Zhang X et al (2003) Enantioconvergent synthesis of (-)-(2R,5 S)-1-allyl-2,5-dimethylpiperazine, an intermediate to d-opioid receptor ligands (2003). J Org Chem 68:3976-3980
61. Tomori H, Shibutami K, Ogura K (1997) Practical synthesis of (S)-3-(p-nitrobenzyloxycar-bonylamino)pyrrolidine and its related compounds from -aspartic acid. Heterocycles 44:213-225