Conformationally constrained butyrophenones with affinity for dopamine (D1, D2, D4) and serotonin (5-HT(2A), 5-HT(2B), 5-HT(2C)) receptors: Synthesis of aminomethylbenzo[b]furanones and their evaluation as antipsychotics

Journal of Medicinal Chemistry

Volumn 43, Issue 24, 2000, Pages 4678-4693

  Ravina, E ^a   Casariego, I ^a   Masaguer, C F ^a   Fontenla, J A ^b   Montenegro, G Y ^b   Rivas, M E ^b   Loza, M I ^b   Enguix, M J ^b   Villazon, M ^b   Cadavid, M I ^b   Demontis, G C ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b Dipartimento di Psichiatria Neurobiologia   (Italy)

^c UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 [[4 (4 CHLOROPHENYL) 1 PIPERAZINYL]METHYL] 1H PYRROLO[2,3 B]PYRIDINE; 4 (4 FLUOROBENZOYL) 1 [(4,5,6,7 TETRAHYDRO 4 OXOBENZO[B]FURAN 6 YL)METHYL]PIPERIDINE; 4 (6 FLUOROBENZISOXAZOL 3 YL) 1 [(4,5,6,7 TETRAHYDRO 4 OXOBENZO[B]FURAN 6 YL)METHYL]PIPERIDINE; 7 (4 FLUOROPHENOXYMETHYL) 2 (5 FLUORO 2 PYRIMIDINYL) 2,3,4,6,7,8,9,9A OCTAHYDROPYRIDO[1,2 A]PYRAZINE; ALPHA (2,3 DIMETHOXYPHENYL) 1 [2 (4 FLUOROPHENYL)ETHYL] 4 PIPERIDINEMETHANOL; AMINOMETHYLBENZO[B]FURANONE; BUTYROPHENONE DERIVATIVE; CLOZAPINE; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; DOPAMINE 4 RECEPTOR; HALOPERIDOL; NEUROLEPTIC AGENT; OCAPERIDONE; OLANZAPINE; QUETIAPINE; REMOXIPRIDE; RISPERIDONE; SEROTONIN 2A RECEPTOR; SEROTONIN 2B RECEPTOR; SEROTONIN 2C RECEPTOR; SERTINDOLE; UNCLASSIFIED DRUG; ZOTEPINE;

ANIMAL BEHAVIOR; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CATALEPSY; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SPECIFICITY; DRUG SYNTHESIS; LOCOMOTION; MALE; MOUSE; NEUROCHEMISTRY; NONHUMAN;

ANIMALS; ANTIPSYCHOTIC AGENTS; BEHAVIOR, ANIMAL; BINDING, COMPETITIVE; BUTYROPHENONES; CATALEPSY; CATTLE; CORPUS STRIATUM; FRONTAL LOBE; HUMANS; ISOXAZOLES; MALE; MICE; PIPERIDINES; RADIOLIGAND ASSAY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, SEROTONIN, 5-HT2A; RECEPTOR, SEROTONIN, 5-HT2B; RECEPTOR, SEROTONIN, 5-HT2C; RECEPTORS, DOPAMINE; RECEPTORS, DOPAMINE D1; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D4; RECEPTORS, SEROTONIN; RETINA;

EID: 0034736151     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0009890     Document Type: Article

References (107)

1. Developments in the drug treatment of schizophrenia
2. Antipsychotic agents
3. Haloperidol-induced catalepsy is mediated by postsynaptic dopamine receptors
4. Human brain dopamine receptors in children and aging adults
5. Conditioned tolerance to haloperidol- and droperidol-induced catalepsy
6. Antipsychotic drug doses and neuroleptic/dopamine receptors
7. Antipsychotic drugs: Direct correlation between clinical potency and presynaptic action on dopamine neurons
8. Relationship of neuroleptic drug effects at brain dopamine, serotonin, alpha-adrenergic, and histamine receptors to clinical potency
9. Clozapine. A review of its pharmacological properties and therapeutic use in schizophrenia
10. An overview of the mechanism of action of clozapine
11. A clinical guide to antipsychotic drugs
12. A comparison of clozapine and haloperidol in hospitalized patients
13. 5-Hydroxytryptamine (serotonin) receptor agonists and antagonists
14. Classification of typical and atypical antipsychotic drugs on the basis of dopamine D-1, D-2 and serotonin-2 pKi values
15. The role of serotonin in schizophrenia
16. Risperidone: A novel antipsychotic with balanced serotonin-dopamine antagonism, receptor occupancy profile, and pharmacologic activity
17. The ratios of serotonin-2 and dopamine-2 affinities differentiate atypical and typical antipsychotic drugs
18. 4 receptor binding affinity does not distinguish between typical and atypical antipsychotic drugs
19. 2 ratio hypothesis
20. The apparent antipsychotic action of the 5-HT2A receptor antagonist MDL 100907 in a mouse model of schizophrenia is counteracted by ritanserin
21. 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
22. Development of a selective 5-HT(2A) receptor antagonist for the treatment of schizophrenia
23. Atypical antipsychotic drugs: Which receptors are relevant?
24. 2 receptor subtypes: A family re-united?
25. Proposed new nomenclature of 5-HT receptors
26. 2 subfamily of receptors: Pharmacological challenges
27. VII international union of pharmacology classification of receptors for 5-hydroxytryptamine (serotonin)
28. Evidence for the expresion of the 5-hydroxytriptamine-2B receptor protein in the rat central nervous system
29. Serotonin receptors in the human brain-III. Autoradiographic mapping of serotonin-1 receptors
30. 5-HT1c receptor is a prominent serotonin receptor subtype in the central nervous system
31. Reciprocal binding properties of 5-hydroxytryptamine type 2C receptor agonists and inverse agonists
32. Constitutively active 5-hydroxytryptamine(2C) receptors reveal novel inverse agonist activity of receptors ligands
33. Attenuation of haloperidol-induced catalepsy by a 5-HT(2C) receptor antagonist
34. Dopamine D4 receptors elevated in schizophrenia
35. 4/5-HT(2A) receptor antagonists: LU-111995 and other potential new antipsychotics in development
36. 3-[[4-(4-Chlorophenyl)piperazin-1-yl]methyl]-1H-pyrrolo[2,3-b]pyridine: An antagonist with high affinity and selectivity for the human dopamine D4 receptor
37. Synthesis, SAR and pharmacology of CP-239, 019: A potent, selective dopamine D4 receptor antagonist
38. Schizophrenia and L-745,870, a novel dopamine D4 receptor antagonist
39. Clozapine-induced agranulocytosis: Non-crossreactivity with other antipsychotic drugs
40. Myocarditis and cardiomyopathy associated with clozapine
41. Synthesis and antidopaminergic activity of some 3-(aminomethyl)tetralones as analogues of butyrophenone
42. Synthesis and atypical antipsychotic profile of some 2-(2-piperidinoethyl) benzocycloalkanones as analogues of butyrophenone
43. 2) and 5-hydroxytryptamine (5-HT(2A)) receptors of 1-(benzoylpropyl)-4-(1-oxocycloalkyl-2-ethyl)piperazines as cyclic butyrophenone derivatives
44. 2 antagonist activity of 3-aminomethyl tetralones
45. 2 and 5-HT(2A) receptors
46. A practical and efficient route for synthesis of 6-aminomethyl-4-oxo-4,5,6,7-tetrahydroindoles as new CNS precursors
47. 2) and serotoninergic (5-HT(2A)) affinities. Synthesis of 5-aminoethyl- and 6-aminomethyl-4-oxotetrahydroindoles as potential atypical antipsychotics
48. 2 and 5-HT(2A) receptors
49. 2, 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors
50. 2) and serotoninergic (5-HT(2A), 5-HT(2C)) affinities: Synthesis, pharmacology, 3D-QSAR and molecular modeling of (aminoalkyl)benzo and -thienocycloalkanones as putative atypical antipsychotics
51. Aroylpiperidines and pyrrolidines. A new class of potent central nervous system depressants
52. 2 serotonin receptor binding
53. [(3-Aryl-1,2-benzisoxazol-6-yl)oxylacetic acids. A new diuretic series
54. Synthesis and neuroleptic activity of 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazoles
55. 2 receptors
56. Ein neue methode zur addition von an aktivierte doppelbindungen, III. Aldehyden addition von aromatischen und heterocyclischen aldehyden an α,β-ungesattigte nitrile
57. Addition von aldehyden an aktivierte doppelbindungen-XII. Ein neuer weg zu 4-oxooctandisauren
58. Addition von aldehyden an aktivierte doppelbindungen, X. Addition von aliphatischen, heterocyclischen und aromatischen aldehyden an α,β-ungesattigte ketone, nitrileund ester
59. A general synthesis of the troponoid system based on solvolysis of 1,4-dihydrobenzyl tosylates
60. Behavioral effects of sertindole, risperidone, clozapine and haloperidol in Cebus monkeys
61. Impairments of movement initiation and execution induced by a blockade of dopamine D1 or D2 receptors are reversed by a blockade of N-methyl-D-aspartate receptors
62. Reserpine attenuates D-amphetamine and MDMA-induced transmitter release in vivo: A consideration of dose, core temperature and dopamine synthesis
63. Effects of the putative D1 antagonist SCH23390 on stereotyped behaviour induced by the D2 agonist RU 24213
64. Differential effects of amphetamine and related compounds on locomotor activity and metabolic rate in mice
65. Effect of pretreatment with amphetamine on the interaction between amphetamine and dopamine neurons in the nucleus accumbens
66. Reversal of amphetamine-induced behaviours by MDL 100,907, a selective 5-HT2A antagonist
67. Differential effects of classical and newer antipsychotics on the hypermotility induced by two dose levels of D-amphetamine
68. Locomotor behaviour of selective agonist DA in mice: Is endogenius dopamine the only catecholamine involved?
69. Amperozide, a new putatively antipsychotic drug with a limbic mode of action on dopamine mediated behaviour
70. The 5-HT2 receptor antagonist MDL 28,133A disrupts the serotonergic-dopaminergic interaction mediating the neurochemical effects of 3,4-methylenedioxymethamphetamine
71. The role of 5-HT2A receptors in antipsychotic activity
72. Evidence for dopamine receptors mediating sedation in the mouse brain
73. Effects of the local application of 3-PPP and sulpiride enantiomer into the nucleus accumbens or into the ventral tegmental area on rat locomotor activity: Evidence for the somatodendritic autorreceptors
74. Climbing behaviour induced by apomorphine in mice: A potential model for the detection of neuroleptic activity
75. SCH23390 may alter dopamine-mediated behaviour via striatal D1 receptors
76. Dopamine D1 receptor agonists combined with the selective quinpirole facilitate the expression of oral stereotyped behaviour in rats
77. Enhanced stereotyped response to apomorphine after chronic D1 blockade with SCH23390
78. Production of climbing behaviour in mice requires both D1 and D2 receptor activation
79. Climbing and stereotyped behaviours in mice require the stimulation of the D1 dopamine receptors
80. Differential ability of selective and nonselective dopamine agonists to induce climbing in the rat indicates the involvement of both D1 and D2 receptors in this behaviour
81. Aporphines as antagonists of dopamine D1 receptors
82. An automated method for the assessment of spontaneous and stereotyped climbing behavior in mice. Effects of the selective D1 and D2 dopamine receptor agonists SKF-38393 and RU-24926 and their association
83. Role of genotype in brain dopamine metabolism and dopamine-dependent behaviour of mice
84. Survey on the pharmacodynamics of the new antipsychotic risperidone
85. Characterization of the 5-HT2 receptor antagonist MDL 100907 as a putative atypical antipsychotic: Behavioral, electrophysiological and neurochemical studies
86. Spontaneous climbing behaviour of mice, its measurement and dopaminergic involvement
87. BW234U (cis-9-[3-(3,5-dimethyl-1-piperazinyl)propyl]carbazole dihydrochloride): A novel antipsychotic agent
88. Catalepsy induced by SCH23390 in rats
89. Quinolinic acid lesions of rat striatum abolish D1 and D2-dopamine receptor-mediated catalepsy
90. Conditioned haloperidol and droperidol-induced catalepsy
91. The effects of drugs on dopamine biosynthesis and metabolism in the rat brain
92. Regulation of monoamine synthesis and utilization by receptors
93. Dopaminergic neurons: Effect of antipsychotic drugs and amphetamine on single cell activity
94. Receptor-mediated control of dopamine metabolism
95. 2 receptor antagonists
96. 2 receptors
97. Proposals for the classification and nomenclature of functional receptors for 5-hydroxytryptamine
98. Quantitative autoradiographic mapping of serotonin receptors in the rat brain II. Serotonin-2 receptors
99. Affinities of fluoxetine, its enantiomers, and other inhibitors of serotonin uptake for subtypes of serotonin receptors
100. A sensitive method for the assay of 5-hydroxytryptamine
101. Cumulative dose-response curves II. Technique for the making of dose-response curves in isolated organs and the evaluation of drug parameters
102. 2 and affinity constants for pharmacological competitive antagonists be estimated?
103. Climbing behavior induced by apomorphine in mice: A simple test for the study of dopamine receptors in striatum
104. Regional studies of catecholamines in rat brain. The disposition of [3H]norepinephrine, [3H]dopamine and [3H]dopa in various regions of the brain