메뉴 건너뛰기




Volumn 49, Issue 25, 2006, Pages 7290-7306

Synthesis and pharmacological evaluation of novel octahydro-1H-pyrido[1,2- a]pyrazine as μ-opioid receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

3 [7,8 DIMETHYL 2 (2 CHLOROBENZYL)OCTAHYDRO 1H PYRIDO[1,2 A]PYRAZIN 8 YL]PHENOL; 3,4 DIMETHYL 4 (3 HYDROXYPHENYL)PIPERIDINE; DELTA OPIATE RECEPTOR; KAPPA OPIATE RECEPTOR; MU OPIATE RECEPTOR; MU OPIATE RECEPTOR ANTAGONIST; NALOXONE; NALTREXONE; OCTAHYDRO 1H PYRIDO[1,2 A]PYRAZINE; PYRAZINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE;

EID: 33845472620     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0604878     Document Type: Article
Times cited : (21)

References (20)
  • 2
    • 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
  • 3
    • 0027448954 scopus 로고
    • Structure-activity relationships of the trans-3,4-dimethyl-4-(3- hydroxyphenyl)piperidine antagonists for μ 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 trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine antagonists for μ 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
  • 5
    • 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, 2262-2265.
    • (1994) J. Med. Chem. , vol.37 , 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
  • 6
    • 15444345625 scopus 로고    scopus 로고
    • 1. Investigation of the N-substituent conformation governing potency and μ receptor subtype selectivity in (+)-(3R,4R)-dimethyl-4-(3-hydraxyphenyl) 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. 1. Investigation of the N-substituent conformation governing potency and μ receptor subtype selectivity in (+)-(3R,4R)-dimethyl-4-(3- hydraxyphenyl)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.10
  • 8
    • 33845477636 scopus 로고    scopus 로고
    • Elucidation of the bioactive conformation of the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine class of μ-opioid receptor antagonists
    • Le Bourdonnec, B.; Goodman, A. J.; Michaut, M.; Graczyk, T. M.; Belanger, S.; Herbertz, T.; DeHaven, R. N.; Dolle, R. E. Elucidation of the bioactive conformation of the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl) piperidine class of μ-opioid receptor antagonists. J. Med. Chem. 2006, 25, 7278-7289.
    • (2006) J. Med. Chem. , vol.25 , pp. 7278-7289
    • Le Bourdonnec, B.1    Goodman, A.J.2    Michaut, M.3    Graczyk, T.M.4    Belanger, S.5    Herbertz, T.6    DeHaven, R.N.7    Dolle, R.E.8
  • 9
    • 0025973653 scopus 로고
    • Synthesis and absolute configuration of LY255582, a potent opioid antagonist
    • Mitch, C. H.; Zimmerman, D. M.; Snoddy, J. D.; Reel, J. K.; Cantrell, B. E. Synthesis and absolute configuration of LY255582, a potent opioid antagonist. J. Org. Chem. 1991, 56, 1660-1663.
    • (1991) J. Org. Chem. , vol.56 , pp. 1660-1663
    • Mitch, C.H.1    Zimmerman, D.M.2    Snoddy, J.D.3    Reel, J.K.4    Cantrell, B.E.5
  • 10
    • 0035843422 scopus 로고    scopus 로고
    • Direct diastereoselective synthesis of (±)-cis- and (+)-trans-4-methylpipecolic acid and derivatives
    • Cossy, J.; Belotti, D. Direct diastereoselective synthesis of (±)-cis- and (+)-trans-4-methylpipecolic acid and derivatives. Tetrahedron Lett. 2001, 42, 2119-2120.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2119-2120
    • Cossy, J.1    Belotti, D.2
  • 11
    • 0347856089 scopus 로고
    • α-Lithioamine synthetic equivalents from dipole-stabilized carbanions. The tert-BOC group as an activator for α′-lithiation of carbamates
    • Beak, P.; Lee, W. K. α-Lithioamine synthetic equivalents from dipole-stabilized carbanions. The tert-BOC group as an activator for α′-lithiation of carbamates. Tetrahedron Lett. 1989, 30, 1197-1200.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 1197-1200
    • Beak, P.1    Lee, W.K.2
  • 12
    • 0000371104 scopus 로고
    • α-Lithioamine synthetic equivalents: Syntheses of diastereoisomers from the Boc-piperidines
    • Beak, P.; Lee, W. K. α-Lithioamine synthetic equivalents: syntheses of diastereoisomers from the Boc-piperidines. J. Org. Chem. 1990, 55, 2578-2580.
    • (1990) J. Org. Chem. , vol.55 , pp. 2578-2580
    • Beak, P.1    Lee, W.K.2
  • 13
    • 33845488619 scopus 로고    scopus 로고
    • note
    • 1H NMR), an additional carboxylic acid derivative, an isomer of 59. The mixture was used for the next step without further purification.
  • 14
    • 33845501525 scopus 로고    scopus 로고
    • note
    • Crystallographic data for compound 62 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 604294. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Rd., Cambridge CB2 1EZ, U.K., (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
  • 15
    • 33845472159 scopus 로고    scopus 로고
    • Chemical Computing Group: 1010 Sherbrooke St. West, Suite 910. Montreal, Quebec H3A 2R, Canada
    • MOE 2004.03; Chemical Computing Group: 1010 Sherbrooke St. West, Suite 910. Montreal, Quebec H3A 2R, Canada.
    • MOE 2004.03
  • 16
    • 0021107965 scopus 로고
    • Solvent-accessible surfaces of proteins and nucleic acids
    • Connolly, M. L. Solvent-accessible surfaces of proteins and nucleic acids. Science 1983, 221, 709-713.
    • (1983) Science , vol.221 , pp. 709-713
    • Connolly, M.L.1
  • 18
    • 0017184389 scopus 로고
    • A Rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. A Rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 19
    • 0031017050 scopus 로고    scopus 로고
    • μ-Opioid receptor-stimulated guanosine-5′-O-(γ-thio)- triphosphate binding in rat thalamus and cultured cell lines: Signal transduction mechanisms underlying agonist efficacy
    • Selley, D. E.; Sim, L. J.; Xiao, R.; Liu, Q.; Childers, S. R. μ-Opioid receptor-stimulated guanosine-5′-O-(γ-thio)-triphosphate binding in rat thalamus and cultured cell lines: signal transduction mechanisms underlying agonist efficacy. Mol. Pharmacol. 1997, 51, 87-96.
    • (1997) Mol. Pharmacol. , vol.51 , pp. 87-96
    • Selley, D.E.1    Sim, L.J.2    Xiao, R.3    Liu, Q.4    Childers, S.R.5
  • 20
    • 0028986870 scopus 로고
    • 35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells
    • 35S]thio)triphosphate binding to membranes from human neuroblastoma SH-SY5Y cells. Mol. Pharmacol. 1995, 47, 848-854.
    • (1995) Mol. Pharmacol. , vol.47 , pp. 848-854
    • Traynor, J.R.1    Nahorski, S.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.