메뉴 건너뛰기




Volumn 40, Issue 20, 1997, Pages 3192-3198

Discovery of a novel class of substituted pyrrolooctahydroisoquinolines as potent and selective δ opioid agonists, based on an extension of the message-address concept

Author keywords

[No Author keywords available]

Indexed keywords

2 [(DIETHYLAMINO)CARBONYL] 6 ETHYL 8A (3 HYDROXYPHENYL) 3 METHYL 4,4A,5,6,7,8,8A OCTAHYDRO 1H PYRROLO[2,3 G]ISOQUINOLINE; 2 [(DIETHYLAMINO)CARBONYL] 6 ETHYL 8A (3 HYDROXYPHENYL) 3 METHYL 4,4A,5,6,7,8,8A,9 OCTAHYDRO 1H PYRROLO[2,3 G]ISOQUINOLINE; 4 [ALPHA (4 ALLYL 2,5 DIMETHYL 1 PIPERAZINYL) 3 METHOXYBENZYL] N,N DIETHYLBENZAMIDE; DELTA OPIATE RECEPTOR AGONIST; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 9844261704     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9608218     Document Type: Article
Times cited : (52)

References (34)
  • 1
    • 0025141368 scopus 로고
    • κ-Opioid Receptor and Analgesia
    • Millan, M. J. κ-Opioid Receptor and Analgesia. Trends Pharmacol. Sci. 1990, 11, 70-76.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 70-76
    • Millan, M.J.1
  • 2
    • 0025960130 scopus 로고
    • Development of Delta Opioid Peptides as Nonaddicting Analgesics
    • Rapaka, R. S.; Porreca F. Development of Delta Opioid Peptides as Nonaddicting Analgesics. Pharm. Res. 1991, 8, 1-8.
    • (1991) Pharm. Res. , vol.8 , pp. 1-8
    • Rapaka, R.S.1    Porreca, F.2
  • 4
    • 0023715894 scopus 로고
    • Direct Dependence Studies in Rats with Agents Selective for Different Types of Opioid Receptor
    • (b) 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 Receptor. 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
  • 6
    • 0021255492 scopus 로고
    • Cerebral Delta Opioid Receptors Mediate Analgesia but not the Intestinal Motility Effects of Intracerebroventricularly Administered Opioids
    • (d) 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 Intracerebroventricularly 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
  • 9
    • 0017620408 scopus 로고
    • ACTH: A Short Introductory Review
    • Schwyzer, R. ACTH: a Short Introductory Review. Ann. N. Y. Acad. Sci. 1977, 297, 3-26.
    • (1977) Ann. N. Y. Acad. Sci. , vol.297 , pp. 3-26
    • Schwyzer, R.1
  • 10
    • 0025314942 scopus 로고
    • Design of Peptidomimetic δ Opioid Receptor Antagonists Using the Message-Address Concept
    • Portoghese, P. S.; Sultana, M.; Takemori, A. E. Design of Peptidomimetic δ Opioid Receptor Antagonists Using the Message-Address Concept. J. Med. Chem. 1990, 33, 1714-1720.
    • (1990) J. Med. Chem. , vol.33 , pp. 1714-1720
    • Portoghese, P.S.1    Sultana, M.2    Takemori, A.E.3
  • 11
    • 0028215413 scopus 로고
    • Potent and Selective Non-peptidic Delta Opioid Ligands Based on the Novel Heterocycle-Condensed Octahydroisoquinoline Structure
    • Dondio, G.; Clarke, G. D.; Giardina, G.; Petrillo, P.; Rapalli, L.; Ronzoni, S.; Vecchietti, V. Potent and Selective Non-peptidic Delta Opioid Ligands Based on The Novel Heterocycle-Condensed Octahydroisoquinoline Structure. Regul. Pept. 1994, 21, 43-44.
    • (1994) Regul. Pept. , vol.21 , pp. 43-44
    • Dondio, G.1    Clarke, G.D.2    Giardina, G.3    Petrillo, P.4    Rapalli, L.5    Ronzoni, S.6    Vecchietti, V.7
  • 12
    • 0001258936 scopus 로고
    • The Role of the "Spacer" in the Octahydroisoquinoline Series: Discovery of SB 213698, a Non-peptidic, Potent and Selective Delta Opioid Agonist
    • Dondio, G.; Clarke, G. D.; Giardina, G.; Petrillo, P.; Petrone, G.; Ronzoni, S.; Visentin, L.; Vecchietti, V. The Role of the "Spacer" in the Octahydroisoquinoline Series: Discovery of SB 213698, a Non-peptidic, Potent and Selective Delta Opioid Agonist. Analgesia 1995, 1 (4-6), 394-399.
    • (1995) Analgesia , vol.1 , Issue.4-6 , pp. 394-399
    • Dondio, G.1    Clarke, G.D.2    Giardina, G.3    Petrillo, P.4    Petrone, G.5    Ronzoni, S.6    Visentin, L.7    Vecchietti, V.8
  • 13
    • 0002789284 scopus 로고
    • Syntheses of Non-peptidic Delta Opioid Agonists and their Structure Activity Relationships
    • (a) Nagase, H.; Wakita, H.; Kawai, K.; Endoh, H.; Matsura, H.; Tanaka, C.; Takezawa, Y. Syntheses of Non-peptidic Delta Opioid Agonists and their Structure Activity Relationships. Jpn. J. Pharmacol. 1994, 64 (Suppl. I), 35.
    • (1994) Jpn. J. Pharmacol. , vol.64 , Issue.SUPPL. I , pp. 35
    • Nagase, H.1    Wakita, H.2    Kawai, K.3    Endoh, H.4    Matsura, H.5    Tanaka, C.6    Takezawa, Y.7
  • 15
    • 0027385389 scopus 로고
    • A Novel, Potent and Selective Non-peptide Delta-receptor Agonist BW 373U86
    • Chang, K. J.; Rigdon, G. C.; Howard, J. L.; McNutt, R. W. A Novel, Potent and Selective Non-peptide Delta-receptor Agonist BW 373U86. 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
  • 16
    • 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- methoxyrjenzyl]-N,N-diethylbenzamide (SNC 80): A Highly Selective, Nonpeptide δ Opioid Receptor Agonist
    • Calderon, S. N.; Rothman, R. B.; Porreca, F.; Flip pen-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- methoxyrjenzyl]-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    Flip pen-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
  • 17
    • 9844249419 scopus 로고    scopus 로고
    • International Patent Application WO95/ 04734 (16.02.95)
    • Dondio, G.; Ronzoni, S. International Patent Application WO95/ 04734 (16.02.95); Chem. Abstr. 1995, 122, 314563j.
    • Dondio, G.1    Ronzoni, S.2
  • 18
    • 9844265185 scopus 로고
    • Dondio, G.; Ronzoni, S. International Patent Application WO95/ 04734 (16.02.95); Chem. Abstr. 1995, 122, 314563j.
    • (1995) Chem. Abstr. , vol.122
  • 19
    • 0006981511 scopus 로고
    • An Efficient Synthesis of the 4a-Aryl-6-oxodecahydroisoquinolines
    • (a) Cantrell, B. E.; Paschal, J. W.; Zimmerman, D. M. An Efficient Synthesis of the 4a-Aryl-6-oxodecahydroisoquinolines. J. Org. Chem. 1989, 54, 1442-1445.
    • (1989) J. Org. Chem. , vol.54 , pp. 1442-1445
    • Cantrell, B.E.1    Paschal, J.W.2    Zimmerman, D.M.3
  • 20
    • 0022548871 scopus 로고
    • Characterization of the Neurotoxic Potential of m-Methoxy-MPTP and Use of its N-Ethyl Analogue as a Means of Avoiding Exposure to a Possible Parkinsonism-Causing Agent
    • (b) Zimmerman, D. M.; Cantrell, B. E.; Reel, J. K.; Hemrick-Luecke, S. K.; Fuller, R. W. Characterization of the Neurotoxic Potential of m-Methoxy-MPTP and Use of its N-Ethyl Analogue as a Means of Avoiding Exposure to a Possible Parkinsonism-Causing Agent. J. Med. Chem. 1986, 29, 1517-1520.
    • (1986) J. Med. Chem. , vol.29 , pp. 1517-1520
    • Zimmerman, D.M.1    Cantrell, B.E.2    Reel, J.K.3    Hemrick-Luecke, S.K.4    Fuller, R.W.5
  • 21
    • 0017360671 scopus 로고
    • Selective N-Dealkylation of Tertiary Amines with Vinyl Chloroformate an Improved Synthesis of Naloxone
    • Olofson, R. A.; Schnur, R. C.; Bunes, L.; Pepe, J. P. Selective N-Dealkylation of Tertiary Amines with Vinyl Chloroformate an Improved Synthesis of Naloxone. Tetrahedron Lett. 1977, 1567-1570.
    • (1977) Tetrahedron Lett. , pp. 1567-1570
    • Olofson, R.A.1    Schnur, R.C.2    Bunes, L.3    Pepe, J.P.4
  • 22
    • 0040975345 scopus 로고
    • The Coupling of Diazonium Salts with Aliphatic Carbon Atoms
    • Adams, R., Blatt, A. H., Boekelheide, V., Cope, A. C., Curtin, D. Y., McGrew; F. C., Niemann, C., Eds; John Wiley & Sons, Inc.: New York
    • Parmerter, S. M. The Coupling of Diazonium Salts with Aliphatic Carbon Atoms. In Organic Reactions; Adams, R., Blatt, A. H., Boekelheide, V., Cope, A. C., Curtin, D. Y., McGrew; F. C., Niemann, C., Eds; John Wiley & Sons, Inc.: New York, 1959; Vol. 10, pp 3-142.
    • (1959) Organic Reactions , vol.10 , pp. 3-142
    • Parmerter, S.M.1
  • 23
    • 35548998916 scopus 로고
    • Monoarylhydrazones of Di- and Tricarbonyl Compounds in the Knorr Synthesis of Pyrroles
    • Shvedov, V. I.; Altukhova, L. B.; Grinev, A. N. Monoarylhydrazones of Di- and Tricarbonyl Compounds in the Knorr Synthesis of Pyrroles. Khimiya Beterot. Soed. 1972, 3, 342-344.
    • (1972) Khimiya Beterot. Soed. , vol.3 , pp. 342-344
    • Shvedov, V.I.1    Altukhova, L.B.2    Grinev, A.N.3
  • 28
    • 84873776176 scopus 로고
    • Method for Evaluating Both Non-Narcotic and Narcotic Analgesics
    • Siegmund, E.; Cadmus, R.; Lu, G. A Method for Evaluating Both Non-Narcotic and Narcotic Analgesics. Proc. Soc. Exp. Biol. Med. 1957, 95, 729-731.
    • (1957) Proc. Soc. Exp. Biol. Med. , vol.95 , pp. 729-731
    • Siegmund, E.1    Cadmus, R.2    Lu, G.A.3
  • 29
    • 0018892679 scopus 로고
    • The Analgetic Properties of Piroxicam in Animals and Correlation with Experimentally Determined Plasma Levels
    • Milne, G. M.; Twomey, T. M. The Analgetic Properties of Piroxicam in Animals and Correlation with Experimentally Determined Plasma Levels. Agents Actions 1980, 10, 31-37.
    • (1980) Agents Actions , vol.10 , pp. 31-37
    • Milne, G.M.1    Twomey, T.M.2
  • 30
    • 0023201480 scopus 로고
    • Metaphit, a Proposed Phencyclidine Receptor Acylator: Disruption of Mouse Motor Behavior and Absence of PCP Antagonist Activity
    • Domino, E. F.; Gole, D.; Koek, W. Metaphit, a Proposed Phencyclidine Receptor Acylator: Disruption of Mouse Motor Behavior and Absence of PCP Antagonist Activity. J. Pharmacol. Exp. Ther. 1987, 243, 95-100.
    • (1987) J. Pharmacol. Exp. Ther. , vol.243 , pp. 95-100
    • Domino, E.F.1    Gole, D.2    Koek, W.3
  • 32
  • 33
    • 0043162336 scopus 로고
    • An Internal Coordinate Monte Carlo Method for Searching Conformational Space
    • Chang, G.; Guida, W. C.; Still, W. C. An Internal Coordinate Monte Carlo Method for Searching Conformational Space. J. Am. Chem. Soc. 1989, 111, 4379-4386.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4379-4386
    • Chang, G.1    Guida, W.C.2    Still, W.C.3
  • 34
    • 9844238981 scopus 로고    scopus 로고
    • note
    • The crystallographic data were not suitable for verifying the absolute configuration of (-)-5b since the anomalous scattering signal was quite weak. However, its absolute configuration may be assigned as 4aS,8aA because the starting material for its synthesis was the same enantiomerically pure ketone (-)-1b used for the synthesis of (+)-3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.