9H-Fluorene-2-carboxylic acid {(E)-4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-but-2-enyl}-amide

ID: ALA304605

Chembl Id: CHEMBL304605

PubChem CID: 44309775

Max Phase: Preclinical

Molecular Formula: C28H27Cl2N3O

Molecular Weight: 492.45

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(NC/C=C/CN1CCN(c2cccc(Cl)c2Cl)CC1)c1ccc2c(c1)Cc1ccccc1-2

Standard InChI:  InChI=1S/C28H27Cl2N3O/c29-25-8-5-9-26(27(25)30)33-16-14-32(15-17-33)13-4-3-12-31-28(34)21-10-11-24-22(19-21)18-20-6-1-2-7-23(20)24/h1-11,19H,12-18H2,(H,31,34)/b4-3+

Standard InChI Key:  ZCTVOGWWMHRQLN-ONEGZZNKSA-N

Associated Targets(Human)

DRD3 Tclin Dopamine D3 receptor (14368 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD2 Tclin Dopamine D2 receptor (23596 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD4 Tchem Dopamine D4 receptor (7907 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD2 Tclin Dopamine receptors; D2 & D3 (635 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD3 Tclin Dopamine receptors; D3 & D4 (312 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Drd3 Dopamine D3 receptor (1050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Drd2 Dopamine D2 receptor (7893 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Drd3 Dopamine receptor D2 and D3 (225 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 492.45Molecular Weight (Monoisotopic): 491.1531AlogP: 5.67#Rotatable Bonds: 6
Polar Surface Area: 35.58Molecular Species: NEUTRALHBA: 3HBD: 1
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: 6.40CX LogP: 6.31CX LogD: 6.26
Aromatic Rings: 3Heavy Atoms: 34QED Weighted: 0.35Np Likeness Score: -1.04

References

1. Newman AH, Cao J, Bennett CJ, Robarge MJ, Freeman RA, Luedtke RR..  (2003)  N-(4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl, butenyl and butynyl)arylcarboxamides as novel dopamine D(3) receptor antagonists.,  13  (13): [PMID:12798330] [10.1016/s0960-894x(03)00389-5]
2. Grundt P, Carlson EE, Cao J, Bennett CJ, McElveen E, Taylor M, Luedtke RR, Newman AH..  (2005)  Novel heterocyclic trans olefin analogues of N-{4-[4-(2,3-dichlorophenyl)piperazin-1-yl]butyl}arylcarboxamides as selective probes with high affinity for the dopamine D3 receptor.,  48  (3): [PMID:15689168] [10.1021/jm049465g]
3. Newman AH, Grundt P, Nader MA..  (2005)  Dopamine D3 receptor partial agonists and antagonists as potential drug abuse therapeutic agents.,  48  (11): [PMID:15916415] [10.1021/jm040190e]
4. Grundt P, Prevatt KM, Cao J, Taylor M, Floresca CZ, Choi JK, Jenkins BG, Luedtke RR, Newman AH..  (2007)  Heterocyclic analogues of N-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butyl)arylcarboxamides with functionalized linking chains as novel dopamine D3 receptor ligands: potential substance abuse therapeutic agents.,  50  (17): [PMID:17672446] [10.1021/jm0704200]
5. Li A, Mishra Y, Malik M, Wang Q, Li S, Taylor M, Reichert DE, Luedtke RR, Mach RH..  (2013)  Evaluation of N-phenyl homopiperazine analogs as potential dopamine D3 receptor selective ligands.,  21  (11): [PMID:23618707] [10.1016/j.bmc.2013.03.074]

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