Adoprazine - CAS 222551-17-9
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
Adoprazine
Catalog Number:
222551-17-9
Synonyms:
1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]piperazine 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-((5-(4-fluorophenyl)-3-pyridinyl)methyl)piperazine SLV 313 SLV-313 SLV313
CAS Number:
222551-17-9
Description:
Adoprazine, also known as SLV 313, with potential antipsychotic property, is a agonist of cloned h5-HT(1A) receptors (pEC(50)=9.0) and a full antagonist of hD(2) (pA(2)=9.3) and hD(3) (pA(2)=8.9) receptors.
Molecular Weight:
405.46
Molecular Formula:
C24H24FN3O2
Quantity:
Data not available, please inquire.
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1CN(CCN1CC2=CN=CC(=C2)C3=CC=C(C=C3)F)C4=C5C(=CC=C4)OCCO5
InChI:
1S/C24H24FN3O2/c25-21-6-4-19(5-7-21)20-14-18(15-26-16-20)17-27-8-10-28(11-9-27)22-2-1-3-23-24(22)30-13-12-29-23/h1-7,14-16H,8-13,17H2
InChIKey:
IUVSEUFHPNITEQ-UHFFFAOYSA-N
Targets:
5-HT Receptor
Chemical Structure
CAS 222551-17-9 Adoprazine

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Reference Reading


1.Synthesis and dual D2 and 5-HT1A receptor binding affinities of 7-piperazinyl and 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones.
Ullah N1. Med Chem. 2014;10(5):484-96.
A series of new 7-piperazinyl and 7-piperidinyl-3,4-dihydroquinazolin-2(1H)-ones has been synthesized. The described compounds are structurally related to adoprazine, a potential atypical antipsychotic bearing potent D2 receptor antagonist and 5-HT1A receptor agonist properties. Suitably modified aryl bromides were prepared and condensed with tert-butyl piperazine-1-carboxylate to afford the advanced intermediate piperazinyl-3,4-dihydroquinazolin-2(1H)-one. Likewise Suzuki-Miyaura cross-coupling reaction of cyclic vinyl boronate with appropriate aryl bromides rendered piperidinyl-3,4-dihydroquinazolin-2(1H)-one. The reductive amination of the piperazinyl and piperidinyl-3,4- dihydroquinazolin-2(1H)-ones with suitably designed biarylaldehydes accomplished the synthesis of these title compounds. The described compounds were screened for D2 and 5-HT1A receptors binding affinities. The structure-activity relationship studies revealed that cyclopentenylpyridine and cyclopentenylbenzyl groups contribute significantly to the dual D2 and 5-HT1A receptor binding affinities of these compounds.
2.Comparative pharmacology of antipsychotics possessing combined dopamine D2 and serotonin 5-HT1A receptor properties.
Newman-Tancredi A1, Kleven MS. Psychopharmacology (Berl). 2011 Aug;216(4):451-73. doi: 10.1007/s00213-011-2247-y. Epub 2011 Mar 11.
RATIONALE: There is increasing interest in antipsychotics intended to manage positive symptoms via D(2) receptor blockade and improve negative symptoms and cognitive deficits via 5-HT(1A) activation. Such a strategy reduces side-effects such as the extrapyramidal syndrome (EPS), weight gain, and autonomic disturbance liability.
3.Dual ligands targeting dopamine D2 and serotonin 5-HT1A receptors as new antipsychotical or anti-Parkinsonian agents.
Ye N, Song Z, Zhang A1. Curr Med Chem. 2014;21(4):437-57.
Psychiatric disorders like schizophrenia and neurodegenerative diseases like Parkinson's disease are associated with poly-factorial pathogenic mechanisms, with several neurotransmitter systems closely involved. In addition to the cerebral dopaminergic (DA) system, the serotoninergic (5-HT) system also plays a crucial role in regulating psychoemotional, cognitive and motor functions in the central nervous system (CNS). Among the large 5-HT receptor family, accumulating data have revealed new insights into the therapeutic benefit of the 5-HT1A receptor in treating various CNS disorders, especially schizophrenia and Parkinson's disease. The present review discusses the advance of dual agents with mixed actions at the dopamine D2 and serotonin 5-HT1A receptors in the treatment of these diseases. Aripiprazole was the only marketed drug with dual D2 and 5-HT1A profile. It is a partial D2 and 5-HT1A receptor agonist and has been prescribed as an atypical antipsychotical drug.