메뉴 건너뛰기




Volumn 41, Issue 21, 1998, Pages 4143-4149

N-substituted 9β-methyl-5-(3-hydroxyphenyl)morphans are opioid receptor pure antagonists

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHYL 4 (3 HYDROXYPHENYL)PIPERIDINE DERIVATIVE; 4 (3 HYDROXYPHENYL)PIPERIDINE DERIVATIVE; 4 [(4 ALLYL 2,5 DIMETHYL 1 PIPERAZINYL) 3 METHOXYBENZYL] N,N DIETHYLBENZAMIDE; 5 (3 HYDROXYPHENYL)MORPHAN DERIVATIVE; DELTA OPIATE RECEPTOR AGONIST; DELTA OPIATE RECEPTOR ANTAGONIST; ENKEPHALIN[2 DEXTRO ALANINE 4 METHYLPHENYLALANINE 5 GLYCINE]; ENKEPHALIN[2 DEXTRO ALANINE 5 DEXTRO LEUCINE]; ETHYLKETAZOCINE; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); KAPPA OPIATE RECEPTOR ANTAGONIST; MU OPIATE RECEPTOR ANTAGONIST; N METHYL 9BETA METHYL 5 (3 HYDROXYPHENYL)MORPHAN DERIVATIVE; N METHYL N [7 (1 PYRROLIDINYL) 1 OXASPIRO[4.5]DEC 8 YL]BENZENEACETAMIDE; N PHENETHYL 9BETA METHYL 5 (3 HYDROXYPHENYL)MORPHAN DERIVATIVE; NALOXONE; NALTREXONE; OPIATE ANTAGONIST; SULFUR 35; TRITIUM; UNCLASSIFIED DRUG; DELTA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR; MORPHINAN DERIVATIVE; MU OPIATE RECEPTOR; N METHYL 9 METHYL 5 (3 HYDROXYPHENYL)MORPHAN; N PHENETHYL 9 METHYL 5 (3 HYDROXYPHENYL)MORPHAN; N-METHYL-9-METHYL-5-(3-HYDROXYPHENYL)MORPHAN; N-PHENETHYL-9-METHYL-5-(3-HYDROXYPHENYL)MORPHAN; OPIATE RECEPTOR;

EID: 15644364959     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980290i     Document Type: Article
Times cited : (31)

References (23)
  • 2
    • 0025232625 scopus 로고
    • Selective opioid receptor agonists and antagonists: Research tools and potential therapeutic agents
    • Zimmerman, D. M.; Leander, J. D. Selective opioid receptor agonists and antagonists: Research tools and potential therapeutic agents. J. Med. Chem. 1990, 33, 895-902.
    • (1990) J. Med. Chem. , vol.33 , pp. 895-902
    • Zimmerman, D.M.1    Leander, J.D.2
  • 3
    • 0030179225 scopus 로고    scopus 로고
    • Opiates, opioids and addiction
    • Kreek, M. J. Opiates, opioids and addiction. Mol Psychiatry 1996, 1 (3), 232-254.
    • (1996) Mol Psychiatry , vol.1 , Issue.3 , pp. 232-254
    • Kreek, M.J.1
  • 4
    • 0027930289 scopus 로고
    • Discovery of a potent, peripherally selective trans-3,4-dimethyl-4-(,3-hydroxyphenyl)-piperidine opioid antagonist for the treatment of gastrointestinal motility disorders
    • Zimmerman, D. M.; Gidda, J. S.; Cantrell, B. E.; Schoepp, D. D.; Johnson, B. G.; Leander, J. D. Discovery of a potent, peripherally selective trans-3,4-dimethyl-4-(,3-hydroxyphenyl)-piperidine opioid antagonist for the treatment of gastrointestinal motility disorders. J. Med. Chem. 1994, 37, 7 (15), 2262-2265.
    • (1994) J. Med. Chem. , vol.7-37 , Issue.15 , pp. 2262-2265
    • Zimmerman, D.M.1    Gidda, J.S.2    Cantrell, B.E.3    Schoepp, D.D.4    Johnson, B.G.5    Leander, J.D.6
  • 5
    • 0018135396 scopus 로고
    • New structural concepts for narcotic antagonists defined in a 4-phenylpiperidine series
    • Zimmerman, D. M.; Nickander, R.; Horng, J. S.; Wong, D. T. New structural concepts for narcotic antagonists defined in a 4-phenylpiperidine series. Nature 1978, 275, 332-334.
    • (1978) Nature , vol.275 , pp. 332-334
    • Zimmerman, D.M.1    Nickander, R.2    Horng, J.S.3    Wong, D.T.4
  • 8
    • 15444345625 scopus 로고    scopus 로고
    • Investigation of the N-substituent conformation governing potency and μ receptor subtype-selectivity in (+)-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)-piperidine opioid antagonists
    • Thomas, J. B.; Mascarella, S. W.; Rothman, R. B.; Partilla, J. S.; Xu, H.; McCullough, K. B.; Dersch, C. M.; Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. Investigation of the N-substituent conformation governing potency and μ receptor subtype-selectivity in (+)-(3R,4R)-dimethyl-4-(3-hydroxyphenyl)-piperidine opioid antagonists. J. Med. Chem. 1998, 41, 1980-1990.
    • (1998) J. Med. Chem. , vol.41 , pp. 1980-1990
    • Thomas, J.B.1    Mascarella, S.W.2    Rothman, R.B.3    Partilla, J.S.4    Xu, H.5    McCullough, K.B.6    Dersch, C.M.7    Cantrell, B.E.8    Zimmerman, D.M.9    Carroll, F.I.10
  • 9
    • 0021270879 scopus 로고
    • Racemic and optically active 2,9-dimethyl-5-(m-hydroxyphenyl)morphans and pharmacological comparison with the 9-demethyl homologues
    • Awaya, H.; May, E. L.; Aceto, M. D.; Merz, H.; Rogers, M. E.; Harris, L. S. Racemic and optically active 2,9-dimethyl-5-(m-hydroxyphenyl)morphans and pharmacological comparison with the 9-demethyl homologues. J. Med. Chem. 1984, 27, 536-539.
    • (1984) J. Med. Chem. , vol.27 , pp. 536-539
    • Awaya, H.1    May, E.L.2    Aceto, M.D.3    Merz, H.4    Rogers, M.E.5    Harris, L.S.6
  • 10
    • 0019134280 scopus 로고
    • Application of metalated enamines to alkaloid synthesis. An expedient approach to the synthesis of morphine-based analgesics
    • Evans, D. A.; Mitch, C. H.; Thomas, R. C.; Zimmerman, D. M.; Robey, R. L. Application of metalated enamines to alkaloid synthesis. An expedient approach to the synthesis of morphine-based analgesics. J. Am. Chem. Soc. 1980, 102, 5955-5956.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 5955-5956
    • Evans, D.A.1    Mitch, C.H.2    Thomas, R.C.3    Zimmerman, D.M.4    Robey, R.L.5
  • 11
    • 0022548871 scopus 로고
    • and references cited in ref 11
    • WARNING: Read the background information relating to analogues of MPTP including references for Zimmerman et al. (J. Med. Chem. 1986, 29, 1517-1520) and references cited in ref 11.
    • (1986) J. Med. Chem. , vol.29 , pp. 1517-1520
    • Zimmerman1
  • 12
    • 0027448954 scopus 로고
    • Structure-activity relationships of the trarcs-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for π and κ opioid receptors
    • Zimmerman, D. M.; Leander, J. D.; Cantrell, B. E.; Reel, J. K.; Snoddy, J.; Mendelsohn, L. G.; Johnson, B. G.; Mitch, C. H. Structure-activity relationships of the trarcs-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for π and κ opioid receptors. J. Med. Chem. 1993, 36, 2833-2841.
    • (1993) J. Med. Chem. , vol.36 , pp. 2833-2841
    • Zimmerman, D.M.1    Leander, J.D.2    Cantrell, B.E.3    Reel, J.K.4    Snoddy, J.5    Mendelsohn, L.G.6    Johnson, B.G.7    Mitch, C.H.8
  • 14
    • 0024438796 scopus 로고
    • Stereochemical influences upon the opioid ligand activities of 4-alkyl-4-arylpiperidine derivatives
    • Casy, A. F.; Dewar, G. H.; Al-Deeb, O. A. A. Stereochemical influences upon the opioid ligand activities of 4-alkyl-4-arylpiperidine derivatives. Chirality 1989, 1, 202-208.
    • (1989) Chirality , vol.1 , pp. 202-208
    • Casy, A.F.1    Dewar, G.H.2    Al-Deeb, O.A.A.3
  • 15
    • 0038185880 scopus 로고
    • Stereochemical studies of the 4-alkyl-4-arylpiperidine class of opioid ligand
    • Casy, A. F.; Dewar, G. H.; Al-Deeb, O. A. A. Stereochemical studies of the 4-alkyl-4-arylpiperidine class of opioid ligand. Magn. Reson. Chem. 1989, 27, 964-972.
    • (1989) Magn. Reson. Chem. , vol.27 , pp. 964-972
    • Casy, A.F.1    Dewar, G.H.2    Al-Deeb, O.A.A.3
  • 16
    • 0015984762 scopus 로고
    • Phenylmorphan agonists-antagonists
    • Ong, H. H.; Oh-ishi, T.; May, E. L. Phenylmorphan agonists-antagonists. J. Med. Chem. 1974, 17, 133-134.
    • (1974) J. Med. Chem. , vol.17 , pp. 133-134
    • Ong, H.H.1    Oh-ishi, T.2    May, E.L.3
  • 17
    • 0019722017 scopus 로고
    • Structural requirements for affinity and intrinsic activity at the opiate receptor defined in 4-phenylpiperidine and related series
    • The Committee on Problems of Drug Dependence, Inc.; NIDA Research Monograph 41; Harris, L. S., Ed.; Committee on Problems of Drug Dependence, Inc.
    • Zimmerman, D. M.; Smits, S. E.; Hynes, M. D.; Cantrell, B. E.; Reamer, M.; Nickander, R. Structural requirements for affinity and intrinsic activity at the opiate receptor defined in 4-phenylpiperidine and related series. In Problems of Drug Dependence, 1982, Proceedings of the 43rd Annual Scientific Meeting, The Committee on Problems of Drug Dependence, Inc.; NIDA Research Monograph 41; Harris, L. S., Ed.; Committee on Problems of Drug Dependence, Inc., 1982; pp 112-118.
    • (1982) Problems of Drug Dependence, 1982, Proceedings of the 43rd Annual Scientific Meeting , pp. 112-118
    • Zimmerman, D.M.1    Smits, S.E.2    Hynes, M.D.3    Cantrell, B.E.4    Reamer, M.5    Nickander, R.6
  • 18
    • 0013800287 scopus 로고
    • A new concept on the mode of interaction of narcotic analgesics with receptors
    • Portoghese, P. S. A new concept on the mode of interaction of narcotic analgesics with receptors. J. Med. Chem. 1965, 8, 609-616.
    • (1965) J. Med. Chem. , vol.8 , pp. 609-616
    • Portoghese, P.S.1
  • 19
    • 0027128743 scopus 로고
    • The role of concepts in structure-activity relationship studies of opioid ligands
    • Portoghese, P. S. The role of concepts in structure-activity relationship studies of opioid ligands. J. Med. Chem. 1992, 35, 1927-1937.
    • (1992) J. Med. Chem. , vol.35 , pp. 1927-1937
    • Portoghese, P.S.1
  • 20
    • 0025256967 scopus 로고
    • Interaction of endogenous opioid peptides and other drugs with four kappa opioid binding sites in guinea pig brain
    • Rothman, R. B.; Bykov, V.; de Costa, B. R.; 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    Bykov, V.2    De Costa, B.R.3    Jacobson, A.E.4    Rice, K.C.5    Brady, L.S.6
  • 21
    • 0025729102 scopus 로고
    • RTI-4614-4: An analogue of (+)-cis-3-methylfentanyl with a 27, 000-fold binding selectivity for mu versus delta opioid 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 analogue of (+)-cis-3-methylfentanyl with a 27, 000-fold binding selectivity for mu versus delta opioid 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
  • 22
    • 0017250843 scopus 로고
    • Statistical characterization of the random errors in the radioimmunoassay dose-response variable
    • Rodbard, D.; Lenox, R. H.; Wray, H. L.; Ramseth, D. Statistical characterization of the random errors in the radioimmunoassay dose-response variable. Clin. Chem. 1976, 22, 350-358.
    • (1976) Clin. Chem. , vol.22 , pp. 350-358
    • Rodbard, D.1    Lenox, R.H.2    Wray, H.L.3    Ramseth, D.4
  • 23
    • 0004150157 scopus 로고
    • Siemens Analytical X-ray Instruments, Inc.: Madison, WI
    • Sheldrick, G. M. SHELXTL-Plus, release 5.03; Siemens Analytical X-ray Instruments, Inc.: Madison, WI, 1995.
    • (1995) SHELXTL-Plus, Release 5.03
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.