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Volumn 42, Issue 15, 1999, Pages 2774-2797

Conformationally constrained butyrophenones with mixed dopaminergic (D2) and serotoninergic (5-HT2(A), 5-HT2(C)) affinities: Synthesis, pharmacology, 3D-QSAR, and molecular modeling of (aminoalkyl)benzo- and - thienocycloalkanones as putative atypical antipsychotics

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BUTYROPHENONE DERIVATIVE; CYCLOALKANONE; DOPAMINE RECEPTOR; NEUROLEPTIC AGENT; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; SEROTONIN RECEPTOR;

EID: 0033614954     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm981094e     Document Type: Article
Times cited : (41)

References (102)
  • 1
    • 77956800115 scopus 로고
    • Novel antipsychotics
    • Bristol, J. A., Ed.; Academic Press: New York
    • For reviews, see: (a) Howard, H. R.; Seeger, T. F. Novel Antipsychotics. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: New York, 1993; Vol. 28, p 39.
    • (1993) Annual Reports in Medicinal Chemistry , vol.28 , pp. 39
    • Howard, H.R.1    Seeger, T.F.2
  • 2
    • 47749124621 scopus 로고    scopus 로고
    • Dopaminergic approachesto antipsychotic agents
    • Bristol, J. A., Ed.; Academic Press: New York
    • (b) Schaus, J. M.; Bymaster, F. P. Dopaminergic Approachesto Antipsychotic Agents. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic Press: New York, 1998; Vol. 33, p 1.
    • (1998) Annual Reports in Medicinal Chemistry , vol.33 , pp. 1
    • Schaus, J.M.1    Bymaster, F.P.2
  • 3
    • 0344937935 scopus 로고
    • Dopamine receptors and dopamine hypothesis of schizophrenia
    • Seeman, P. Dopamine receptors and dopamine hypothesis of schizophrenia. Synapse 1987, 192, 481-483.
    • (1987) Synapse , vol.192 , pp. 481-483
    • Seeman, P.1
  • 4
    • 0344075895 scopus 로고
    • Current trends in antipsychotic agents
    • PJB Publications: Richmond, U.K.
    • Sitsen, A. Current trends in antipsychotic agents. Script Report; PJB Publications: Richmond, U.K., 1990; p 57.
    • (1990) Script Report , pp. 57
    • Sitsen, A.1
  • 5
    • 0017068246 scopus 로고
    • Antipsychotic drug doses and neuroleptic/dopamine receptors
    • Seeman, P.; Chou-Wong, M.; Tadesco, J.; Wong, K. Antipsychotic drug doses and neuroleptic/dopamine receptors. Nature 1976, 261, 717-719.
    • (1976) Nature , vol.261 , pp. 717-719
    • Seeman, P.1    Chou-Wong, M.2    Tadesco, J.3    Wong, K.4
  • 8
    • 0025599851 scopus 로고
    • A review of its pharmacological properties and therapeutic use in schizophrenia
    • Filton, A.; Heel, R. C. Clozapine. A review of its pharmacological properties and therapeutic use in schizophrenia. Drugs 1990, 40, 722-747.
    • (1990) Drugs , vol.40 , pp. 722-747
    • Filton, A.1    Heel, R.2    Clozapine, C.3
  • 9
    • 0027102729 scopus 로고
    • A clinical guide to antipsychotic drugs
    • Schwarz, J. T.; Brotman, A. W. A clinical guide to antipsychotic drugs. Drugs 1992, 44, 981-992.
    • (1992) Drugs , vol.44 , pp. 981-992
    • Schwarz, J.T.1    Brotman, A.W.2
  • 10
    • 0030756517 scopus 로고    scopus 로고
    • A comparison of clozapine and haloperidol in hospitalized patients
    • Rosenheck, R.; Cramer, J.; Xu, W.; Henderson, W.; Frismann, L. A comparison of clozapine and haloperidol in hospitalized patients. N. Engl. J. Med. 1997, 337, 809-815.
    • (1997) N. Engl. J. Med. , vol.337 , pp. 809-815
    • Rosenheck, R.1    Cramer, J.2    Xu, W.3    Henderson, W.4    Frismann, L.5
  • 11
    • 0029688430 scopus 로고    scopus 로고
    • 2/D2 antagonists: A new type of antipsychotic agent
    • Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Sci.: Amsterdam
    • 2/D2 Antagonists: a new type of antipsychotic agent. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier Sci.: Amsterdam, 1996; Vol. 33, p 186.
    • (1996) Progress in Medicinal Chemistry , vol.33 , pp. 186
    • Megens, A.H.P.1    Kennis, L.E.J.2
  • 12
    • 0030065502 scopus 로고    scopus 로고
    • Olanzapine versus placebo and haloperidol: Acute phase results of the North American Double-blind Olanzapine Trial
    • (b) Beasley, C. M.; Tollefson, G.; Tran, P.; Satterlee, W.; Sanger, T.; Hamilton, S. Olanzapine versus placebo and haloperidol: Acute phase results of the North American Double-Blind Olanzapine Trial. Neuropsychopharmacology 1996, 14, 111-123.
    • (1996) Neuropsychopharmacology , vol.14 , pp. 111-123
    • Beasley, C.M.1    Tollefson, G.2    Tran, P.3    Satterlee, W.4    Sanger, T.5    Hamilton, S.6
  • 13
    • 0030689616 scopus 로고    scopus 로고
    • Evaluation of treatment-resistant schizophrenia
    • (c) Conley, R. R.; Buchanan, R. W. Evaluation of treatment-resistant schizophrenia. Schizophrenia Bull. 1997, 23, 663-674.
    • (1997) Schizophrenia Bull. , vol.23 , pp. 663-674
    • Conley, R.R.1    Buchanan, R.W.2
  • 14
    • 0000372083 scopus 로고    scopus 로고
    • 5-Hydroxytryptamine (Serotonin) receptor agonists and antagonists
    • Hardman, J. G., Limbird, L. E., Molinoff, P. B., Ruddon, R. W., Goodman, A., Eds.; McGraw-Hill: New York
    • Sanders-Bush, E.; Mayer, S. E. 5-Hydroxytryptamine (Serotonin) Receptor Agonists and Antagonists. In The Pharmacological Basis of Therapeutics, 9th ed.; Hardman, J. G., Limbird, L. E., Molinoff, P. B., Ruddon, R. W., Goodman, A., Eds.; McGraw-Hill: New York, 1996; pp 249-263.
    • (1996) The Pharmacological Basis of Therapeutics, 9th Ed. , pp. 249-263
    • Sanders-Bush, E.1    Mayer, S.E.2
  • 15
    • 0024466603 scopus 로고
    • Classification of typical and atypical antipsychotic drugs on the basis of dopamine D-1, D-2 and serotonin2 pKi values
    • Meltzer, H. Y.; Matsubara, S.; Lee, J. C. Classification of typical and atypical antipsychotic drugs on the basis of dopamine D-1, D-2 and serotonin2 pKi values. J. Pharmacol. Exp. Ther. 1989, 251, 238-246.
    • (1989) J. Pharmacol. Exp. Ther. , vol.251 , pp. 238-246
    • Meltzer, H.Y.1    Matsubara, S.2    Lee, J.C.3
  • 16
    • 0001792366 scopus 로고
    • The role of Serotonin in Schizophenia
    • Bloom, F. E., Kupfer, D. J., Eds.; Raven Press: New York
    • Roth, B. L.; Meltzer, H. Y. The role of Serotonin in Schizophenia. In Psychopharmacology: The Fourth Generation of Progress; Bloom, F. E., Kupfer, D. J., Eds.; Raven Press: New York, 1995; pp 1215-1227.
    • (1995) Psychopharmacology: The Fourth Generation of Progress , pp. 1215-1227
    • Roth, B.L.1    Meltzer, H.Y.2
  • 17
    • 0024854809 scopus 로고
    • The ratios of serotonin2 and dopamine2 affinities differentiate atypical and typical antipsychotic drugs
    • Meltzer, H. Y.; Matsubara, S.; Lee, J. C. The ratios of serotonin2 and dopamine2 affinities differentiate atypical and typical antipsychotic drugs. Psychopharmacol. Bull. 1989, 25, 390-392.
    • (1989) Psychopharmacol. Bull. , vol.25 , pp. 390-392
    • Meltzer, H.Y.1    Matsubara, S.2    Lee, J.C.3
  • 19
    • 0029988896 scopus 로고    scopus 로고
    • Serotonin-dopamine interaction and its relevance to schizophrenia
    • Kapur, S.; Remington, G. Serotonin-Dopamine Interaction and Its Relevance to Schizophrenia. Am. J. Psychiatry 1996, 153, 466-476.
    • (1996) Am. J. Psychiatry , vol.153 , pp. 466-476
    • Kapur, S.1    Remington, G.2
  • 21
    • 0031023562 scopus 로고    scopus 로고
    • Blockade of phencyclidine-induced hyperlocomotion by olanzapine, clozapine and serotonin receptor subtype selective antagonists in mice
    • Gleason, S. D.; Shannon, H. E. Blockade of phencyclidine-induced hyperlocomotion by olanzapine, clozapine and serotonin receptor subtype selective antagonists in mice. Psychopharmacology (Berlin) 1997, 129, 79-84.
    • (1997) Psychopharmacology (Berlin) , vol.129 , pp. 79-84
    • Gleason, S.D.1    Shannon, H.E.2
  • 22
    • 0030750579 scopus 로고    scopus 로고
    • 2A receptors in the ventral pallidum
    • 2A receptors in the ventral pallidum. Brain Res. 1997, 761, 97-104.
    • (1997) Brain Res. , vol.761 , pp. 97-104
    • Sipes, T.E.1    Geyer, M.A.2
  • 25
    • 0030766908 scopus 로고    scopus 로고
    • The apparent antipsychotic action of the 5-HT2A receptor antagonist MDL 100907 in a mouse model of schizophrenia is counteracted by ritanserin
    • Martin, P.; Waters, N.; Carlsson, A.; Carlsson, M. L. The apparent antipsychotic action of the 5-HT2A receptor antagonist MDL 100907 in a mouse model of schizophrenia is counteracted by ritanserin. J. Neural. Transm. 1997, 104, 561-564.
    • (1997) J. Neural. Transm. , vol.104 , pp. 561-564
    • Martin, P.1    Waters, N.2    Carlsson, A.3    Carlsson, M.L.4
  • 26
    • 0029930333 scopus 로고    scopus 로고
    • 5-HT modulation of auditory and visual sensorimotor gating: II. Effects of the 5-HT2A antagonist MDL 100, 907 on disruption of sound and light prepulse inhibition produced by 5-HT agonists in Wistar rats
    • Padich, R. A.; McCloskey T. C.; Kehne, J. H. 5-HT modulation of auditory and visual sensorimotor gating: II. Effects of the 5-HT2A antagonist MDL 100, 907 on disruption of sound and light prepulse inhibition produced by 5-HT agonists in Wistar rats. Psychopharmacology 1996, 124, 107-116.
    • (1996) Psychopharmacology , vol.124 , pp. 107-116
    • Padich, R.A.1    McCloskey T, C.2    Kehne, J.H.3
  • 27
    • 0345018695 scopus 로고    scopus 로고
    • 2A receptor antagonist for the treatment of schizophrenia
    • Central Nervous System. Targets for New Therapeutic Agents, Philadelphia, PA
    • 2A receptor antagonist for the treatment of schizophrenia. IBS's International Conference on Serotonin Receptors. Central Nervous System. Targets for New Therapeutic Agents, Philadelphia, PA, 1996.
    • (1996) IBS's International Conference on Serotonin Receptors
    • Schmidt, C.J.1
  • 28
    • 0006986902 scopus 로고    scopus 로고
    • Atypical antipsychotic drugs: Which receptors are relevant?
    • Central Nervous System. Targets for New Therapeutic Agents, Philadelphia, PA
    • Meltzer, H. Y. Atypical antipsychotic drugs: which receptors are relevant? IBS's International Conference on Serotonin Receptors. Central Nervous System. Targets for New Therapeutic Agents, Philadelphia, PA, 1996.
    • (1996) IBS's International Conference on Serotonin Receptors
    • Meltzer, H.Y.1
  • 29
    • 26344444622 scopus 로고    scopus 로고
    • Multiple serotonin/dopamine receptor interactions contribute to atypical antipsychotic drug action
    • Meltzer, H. Y. Multiple serotonin/dopamine receptor interactions contribute to atypical antipsychotic drug action. Eur. Neuropsychopharmacol. 1996, 6, S-32-2.
    • (1996) Eur. Neuropsychopharmacol. , vol.6
    • Meltzer, H.Y.1
  • 31
    • 0027481384 scopus 로고
    • Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs
    • Monsma, F. J.; Shen, Y.; Ward, R. P.; Hamblin, M. W.; Sibley, D. R. Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs. Mol. Pharmacol. 1992, 43, 320-327.
    • (1992) Mol. Pharmacol. , vol.43 , pp. 320-327
    • Monsma, F.J.1    Shen, Y.2    Ward, R.P.3    Hamblin, M.W.4    Sibley, D.R.5
  • 32
    • 0028896011 scopus 로고
    • Localization of serotonin subtype 6 receptor messenger RNA in the rat brain by in situ hybridization histochemistry
    • Ward, R. P.; Hamblin, M. W.; Lachowicz, J. E.; Hoffman, B. J.; Sibley, D. R.; Dorsa, D. M. Localization of serotonin subtype 6 receptor messenger RNA in the rat brain by in situ hybridization histochemistry. Neuroscience 1995, 1105-1111.
    • (1995) Neuroscience , pp. 1105-1111
    • Ward, R.P.1    Hamblin, M.W.2    Lachowicz, J.E.3    Hoffman, B.J.4    Sibley, D.R.5    Dorsa, D.M.6
  • 33
    • 13344280365 scopus 로고    scopus 로고
    • Classification and nomenclature of 5-HT receptors: A comment on current issues
    • (a) Hoyer, D.; Martin, G. R. Classification and nomenclature of 5-HT receptors: a comment on current issues. Behav. Brain Res. 1996, 73, 263-268.
    • (1996) Behav. Brain Res. , vol.73 , pp. 263-268
    • Hoyer, D.1    Martin, G.R.2
  • 36
    • 0023743162 scopus 로고
    • Novel antipsychotic drugs share high affinity for sigma receptors
    • Largent, B. L.; Wikstrom, H.; Snowman, A. M.; Snyder, S. H. Novel antipsychotic drugs share high affinity for sigma receptors. Eur. J. Pharmacol. 1988, 155, 345-347.
    • (1988) Eur. J. Pharmacol. , vol.155 , pp. 345-347
    • Largent, B.L.1    Wikstrom, H.2    Snowman, A.M.3    Snyder, S.H.4
  • 38
    • 0026512839 scopus 로고
    • Behavioral disinhibition and depression in amphetaminized rats: A comparison of risperidone, ocaperidone and haloperidol
    • Megens, A. A. H. P.; Niemegeers, C. J. E.; Awouters, F. H. L. Behavioral disinhibition and depression in amphetaminized rats: A comparison of risperidone, ocaperidone and haloperidol. J. Pharmacol. Exp. Ther. 1992, 260, 160-167.
    • (1992) J. Pharmacol. Exp. Ther. , vol.260 , pp. 160-167
    • Megens, A.A.H.P.1    Niemegeers, C.J.E.2    Awouters, F.H.L.3
  • 49
    • 0030586191 scopus 로고    scopus 로고
    • A practical and efficient route for synthesis of 6-aminomethyl-4-oxo-4,5,6,7-tetrahydroindoles as new CNS precursors
    • Masaguer, C. F.; Raviña, E. A practical and efficient route for synthesis of 6-aminomethyl-4-oxo-4,5,6,7-tetrahydroindoles as new CNS precursors. Tetrahedron Lett. 1996, 37, 5171-5174.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5171-5174
    • Masaguer, C.F.1    Raviña, E.2
  • 50
    • 0033032752 scopus 로고    scopus 로고
    • 2A) affinities. Synthesis of 5-aminoethyl-and 6-aminomethyl-4-oxotetrahydroindoles as potential atypical antipsychotics
    • 2A) affinities. Synthesis of 5-aminoethyl-and 6-aminomethyl-4-oxotetrahydroindoles as potential atypical antipsychotics. Chem. Pharm. Bull. 1999, 47.
    • (1999) Chem. Pharm. Bull. , pp. 47
    • Masaguer, C.F.1    Casariego, I.2    Raviña, E.3
  • 56
    • 0344842841 scopus 로고
    • Friedel-crafts reaction of benzene with 2-Phenylbutanedioic anhydride
    • Hashimoto, I.; Takatsuka, R. Friedel-Crafts Reaction of Benzene with 2-Phenylbutanedioic Anhydride. Bull. Chem. Soc. Jpn. 1977, 50, 2495-2496.
    • (1977) Bull. Chem. Soc. Jpn. , vol.50 , pp. 2495-2496
    • Hashimoto, I.1    Takatsuka, R.2
  • 57
    • 0011850124 scopus 로고
    • A new reagent for activating carboxyl groups; preparation and reactions of N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride
    • Diago-Meseguer, J.; Palomo-Coll, A. L.; Fernández-Lizarbe, J. R.; Zugaza-Bilbao, A. A new reagent for activating carboxyl groups; preparation and reactions of N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride. Synthesis 1980, 547-551.
    • (1980) Synthesis , pp. 547-551
    • Diago-Meseguer, J.1    Palomo-Coll, A.L.2    Fernández-Lizarbe, J.R.3    Zugaza-Bilbao, A.4
  • 58
    • 84985204874 scopus 로고    scopus 로고
    • Der phenylacetyl-(PhAc-)rest als enzymatisch ablösbare schutzgruppe für peptide und kohlenhydrate: Selektrive schutzgruppenabspaltungen mit penicillin-acylase
    • Waldmann, H. Der Phenylacetyl-(PhAc-)Rest als enzymatisch ablösbare Schutzgruppe für Peptide und Kohlenhydrate: Selektrive Schutzgruppenabspaltungen mit Penicillin-Acylase. Liebigs Ann. Chem. 1998, 1175-1180.
    • (1998) Liebigs Ann. Chem. , pp. 1175-1180
    • Waldmann, H.1
  • 59
    • 0000169587 scopus 로고
    • A facile procedure for acetalization under aprotic conditions
    • Tsunada, T.; Suzuki, M.; Noyori, R. A facile procedure for acetalization under aprotic conditions. Tetrahedron Lett. 1980, 21, 1357-1358.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1357-1358
    • Tsunada, T.1    Suzuki, M.2    Noyori, R.3
  • 60
    • 0344166723 scopus 로고    scopus 로고
    • note
    • 3Si/TFA reductions were unsuccessful.
  • 61
    • 0345460427 scopus 로고    scopus 로고
    • note
    • Attempted ring closure with TFA-acetic anhydride invariably gave the 2-acetylthiophene derivative in quantitative yield.
  • 62
    • 0345460430 scopus 로고    scopus 로고
    • note
    • With the exception of 35b, all chiral compounds described in this work are racemic mixtures.
  • 63
    • 0345460431 scopus 로고    scopus 로고
    • note
    • Chromatography was performed using a Beckman System Gold HPLC system with a column containing cellulose-based chiral stationary phase (Chiracel, OD 250 × 10 mm), i-PrOH-hexane (20:80) as solvent, and a flow rate of 0.5 mL/min.
  • 64
    • 0344166722 scopus 로고    scopus 로고
    • note
    • 2A) = 7.83.
  • 65
    • 0023751431 scopus 로고
    • Comparative Molecular Field Analysis (CoMFA). 1. Effects of shape on binding of steroids to carrier protein
    • Cramer, R. D.; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effects of shape on binding of steroids to carrier protein. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer, R.D.1    Patterson, D.E.2    Bunce, J.D.3
  • 67
    • 0002825636 scopus 로고
    • Applications of CoMFA and related 3D-QSAR approaches
    • Kubinyi, H., Ed.; Escom: Leiden
    • Thibaut, U. Applications of CoMFA and Related 3D-QSAR Approaches. In Drug Design: Theory, Methods and Applications; Kubinyi, H., Ed.; Escom: Leiden, 1993; pp 661-696.
    • (1993) Drug Design: Theory, Methods and Applications , pp. 661-696
    • Thibaut, U.1
  • 68
    • 0028411658 scopus 로고
    • Molecular lipophilicity potential, a tool in 3D-QSAR: Method and applications
    • Gaillard, P.; Carrupt, P.-A.; Testa, B.; Boudon, A. Molecular lipophilicity potential, a tool in 3D-QSAR: Method and applications. J. Comput.-Aided Mol. Des. 1994, 8, 83-96.
    • (1994) J. Comput.-aided Mol. Des. , vol.8 , pp. 83-96
    • Gaillard, P.1    Carrupt, P.-A.2    Testa, B.3    Boudon, A.4
  • 69
    • 0002368625 scopus 로고    scopus 로고
    • Intramolecular interactions encoded in lipophilicity
    • Pliska, V., Testa, B., van der Waterbeemd, H., Eds.; VCH: Weinheim
    • Testa, B.; Carrupt, P.-A.; Gaillard, P.; Tsai, R. S. Intramolecular Interactions Encoded in Lipophilicity. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van der Waterbeemd, H., Eds.; VCH: Weinheim, 1997; pp 49-71.
    • (1997) Lipophilicity in Drug Action and Toxicology , pp. 49-71
    • Testa, B.1    Carrupt, P.-A.2    Gaillard, P.3    Tsai, R.S.4
  • 70
    • 0002309097 scopus 로고
    • PLS - Partial Least Squares Projections to Latent Structures
    • Kubinyi, H., Ed.; Escom: Leiden
    • Wold, S.; Johansson, E.; Cocchi, M. PLS - Partial Least Squares Projections to Latent Structures. In Drug Design: Theory, Methods and Applications; Kubinyi, H., Ed.; Escom: Leiden, 1993; pp 523-549.
    • (1993) Drug Design: Theory, Methods and Applications , pp. 523-549
    • Wold, S.1    Johansson, E.2    Cocchi, M.3
  • 71
    • 84987100711 scopus 로고
    • Crossvalidation, bootstrapping and Partial Least Squares compared with multiple regression analysis
    • Cramer, R. D., III; Bunce, J. D.; Patterson, D. E. Crossvalidation, bootstrapping and Partial Least Squares compared with Multiple Regression Analysis. Quant. Struct.-Act. Relat. 1988, 7, 18-25.
    • (1988) Quant. Struct.-act. Relat. , vol.7 , pp. 18-25
    • Cramer R.D. III1    Bunce, J.D.2    Patterson, D.E.3
  • 72
    • 0344166720 scopus 로고    scopus 로고
    • note
    • 40
  • 73
    • 0345029293 scopus 로고    scopus 로고
    • note
    • 2 for the congeneric (o-methoxyphenyl)-piperazine derivatives If, IIIf, 10f, and 24f.
  • 75
    • 0025390935 scopus 로고
    • MOPAC: A semiempirical molecular orbital program
    • Stewart, J. J. P. MOPAC: A semiempirical molecular orbital program. J. Comput.-Aided Mol. Des. 1990, 4, 1-103.
    • (1990) J. Comput.-aided Mol. Des. , vol.4 , pp. 1-103
    • Stewart, J.J.P.1
  • 77
    • 0344778061 scopus 로고
    • Semianalytical treatment of solvation for molecular mechanics and dynamics
    • Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. Semianalytical treatment of solvation for molecular mechanics and dynamics. J. Am. Chem. Soc. 1990, 112, 6127-6129.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 6127-6129
    • Still, W.C.1    Tempczyk, A.2    Hawley, R.C.3    Hendrickson, T.4
  • 78
    • 84900531145 scopus 로고    scopus 로고
    • Statistical validation of QSAR results
    • van de Waterbeemd, H., Ed.; VCH: Weinheim
    • Wold, S.; Eriksson, L. Statistical Validation of QSAR Results. In Chemometric Methods in Molecular Design; van de Waterbeemd, H., Ed.; VCH: Weinheim, 1996; pp 309-318.
    • (1996) Chemometric Methods in Molecular Design , pp. 309-318
    • Wold, S.1    Eriksson, L.2
  • 81
    • 0027506471 scopus 로고
    • The probable arrangement of the helices in G protein-coupled receptors
    • Baldwin, J. M. The probable arrangement of the helices in G protein-coupled receptors. EMBO J. 1993, 12, 1693-1703.
    • (1993) EMBO J. , vol.12 , pp. 1693-1703
    • Baldwin, J.M.1
  • 83
    • 0000243829 scopus 로고
    • Procheck: A program to check the stereochemical quality of protein structures
    • Laskowski, R. A.; MacArthur, M. W.; Moss, D. S.; Thornton, J. M. Procheck: a program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 1993, 26, 283-291.
    • (1993) J. Appl. Crystallogr. , vol.26 , pp. 283-291
    • Laskowski, R.A.1    MacArthur, M.W.2    Moss, D.S.3    Thornton, J.M.4
  • 85
    • 0024847889 scopus 로고
    • Site-directed mutagenesis of m1 muscarinic receptors: Conserved aspartic acids play important roles in receptor function
    • Fraser, C. M.; Wang, C. D.; Robinson, D. A.; Gocayne, J. D.; Venter, J. C. Site-directed mutagenesis of m1 muscarinic receptors: conserved aspartic acids play important roles in receptor function. Mol. Pharmacol. 1989, 36, 840-847.
    • (1989) Mol. Pharmacol. , vol.36 , pp. 840-847
    • Fraser, C.M.1    Wang, C.D.2    Robinson, D.A.3    Gocayne, J.D.4    Venter, J.C.5
  • 86
    • 0024519931 scopus 로고
    • Structural basis of α-adrenergic receptor function
    • Strader, C. D.; Sigal, I. S.; Dixon, R. A. F. Structural basis of α-adrenergic receptor function. FASEB J. 1989, 3, 1825-1832.
    • (1989) FASEB J. , vol.3 , pp. 1825-1832
    • Strader, C.D.1    Sigal, I.S.2    Dixon, R.A.F.3
  • 88
    • 0344166716 scopus 로고    scopus 로고
    • Molecular Simulations Inc., San Diego, CA
    • (82) Molecular Simulations Inc., San Diego, CA.
    • , vol.82
  • 90
    • 0037891296 scopus 로고
    • Thiaindanones. Thiophene isosters of indanone
    • Sam, J.; Thompson, A. C. Thiaindanones. Thiophene isosters of indanone. J. Pharm. Sci. 1963, 52, 898-901.
    • (1963) J. Pharm. Sci. , vol.52 , pp. 898-901
    • Sam, J.1    Thompson, A.C.2
  • 91
    • 0006930017 scopus 로고
    • Some reactions of 4-oxo-4,5,6,7-tetrahydrothianaphthene
    • Nishimura, S.; Nakamura, M.; Suzuki, M.; Imoto, E. Some reactions of 4-oxo-4,5,6,7-tetrahydrothianaphthene. Nippon Kagaku Zasshi 1962, 83, 343-347; Chem. Abstr. 1963, 59, 3862c.
    • (1962) Nippon Kagaku Zasshi , vol.83 , pp. 343-347
    • Nishimura, S.1    Nakamura, M.2    Suzuki, M.3    Imoto, E.4
  • 92
    • 84917990618 scopus 로고
    • Nishimura, S.; Nakamura, M.; Suzuki, M.; Imoto, E. Some reactions of 4-oxo-4,5,6,7-tetrahydrothianaphthene. Nippon Kagaku Zasshi 1962, 83, 343-347; Chem. Abstr. 1963, 59, 3862c.
    • (1963) Chem. Abstr. , vol.59
  • 93
    • 0342392549 scopus 로고
    • Contribution a l'etude des hétérocycles soufrés condensés. V. Substitution dans le noyau du tétrahydro-4-5-6-7 thionaphtène au moyen de la réaction de friedel-crafts
    • Cagniant, M. P.; Cagniant, P. Contribution a l'etude des hétérocycles soufrés condensés. V. Substitution dans le noyau du tétrahydro-4-5-6-7 thionaphtène au moyen de la réaction de Friedel-Crafts. Bull. Soc. Chim. Fr. 1953, 20, 62-69.
    • (1953) Bull. Soc. Chim. Fr. , vol.20 , pp. 62-69
    • Cagniant, M.P.1    Cagniant, P.2
  • 94
    • 0010544777 scopus 로고
    • Syntheses dans le domaine des methoxy oxo-4 et oxo-7 tetrahydro-4,5,6,7 benzo[6]thiophenes
    • Conjat, J. P.; Cagniant, P.; Cagniant, D.; Mirjolet, M. Syntheses dans le domaine des methoxy oxo-4 et oxo-7 tetrahydro-4,5,6,7 benzo[6]thiophenes. Tetrahedron Lett. 1975, 2885-2888.
    • (1975) Tetrahedron Lett. , pp. 2885-2888
    • Conjat, J.P.1    Cagniant, P.2    Cagniant, D.3    Mirjolet, M.4
  • 95
    • 0017119483 scopus 로고
    • Climbing behavior induced by apomorphine in mice: A simple test for the study of dopamine receptors in striatum
    • Protais, P.; Costentin, J.; Schwartz, J. C. Climbing behavior induced by apomorphine in mice: A simple test for the study of dopamine receptors in striatum. Psychopharmacology 1976, 50, 1-6.
    • (1976) Psychopharmacology , vol.50 , pp. 1-6
    • Protais, P.1    Costentin, J.2    Schwartz, J.C.3
  • 98
    • 0022401097 scopus 로고
    • Quantitative autoradiographic mapping of serotonin receptors in the rat brain II. Serotonin-2 receptors
    • Pazos, A.; Cortes, R.; Palacios, J. M. Quantitative autoradiographic mapping of serotonin receptors in the rat brain II. Serotonin-2 receptors. Brain Res. 1985, 346, 231-245.
    • (1985) Brain Res. , vol.346 , pp. 231-245
    • Pazos, A.1    Cortes, R.2    Palacios, J.M.3
  • 99
    • 0025771565 scopus 로고
    • Affinities of fluoxetine, its enantiomers, and other inhibitors of serotonin uptake for subtypes of serotonin receptors
    • Wong, D. T.; Threlkeld, P. G.; Robertson, D. W. Affinities of fluoxetine, its enantiomers, and other inhibitors of serotonin uptake for subtypes of serotonin receptors. Neuropsychopharmacology 1991, 5, 43-47.
    • (1991) Neuropsychopharmacology , vol.5 , pp. 43-47
    • Wong, D.T.1    Threlkeld, P.G.2    Robertson, D.W.3
  • 100
    • 0022535631 scopus 로고
    • Mechanisms of extraneuronal serotonin uptake in the rat aorta
    • Fukuda, S.; Su, C.; Lee, T. J. F. Mechanisms of extraneuronal serotonin uptake in the rat aorta. J. Pharmacol. Exp. Ther. 1986, 239, 264-269.
    • (1986) J. Pharmacol. Exp. Ther. , vol.239 , pp. 264-269
    • Fukuda, S.1    Su, C.2    Lee, T.J.F.3
  • 101
    • 0026663904 scopus 로고
    • Potentiation of 5-hydroxytryptamine-induced contraction in rat aorta by chlorpheniramine, citalopram and fluoxetine
    • Gruetter, C. A.; Lemke, S. M.; Anestis, D. K.; Szarek, J. L.; Valentovic, M. A. Potentiation of 5-hydroxytryptamine-induced contraction in rat aorta by chlorpheniramine, citalopram and fluoxetine. Eur. J. Pharmacol. 1992, 217, 109-118.
    • (1992) Eur. J. Pharmacol. , vol.217 , pp. 109-118
    • Gruetter, C.A.1    Lemke, S.M.2    Anestis, D.K.3    Szarek, J.L.4    Valentovic, M.A.5


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