ID: ALA1627305

Max Phase: Preclinical

Molecular Formula: C23H26Cl2N4O2

Molecular Weight: 461.39

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(NCCC(O)CN1CCN(c2cccc(Cl)c2Cl)CC1)c1cc2ccccc2[nH]1

Standard InChI:  InChI=1S/C23H26Cl2N4O2/c24-18-5-3-7-21(22(18)25)29-12-10-28(11-13-29)15-17(30)8-9-26-23(31)20-14-16-4-1-2-6-19(16)27-20/h1-7,14,17,27,30H,8-13,15H2,(H,26,31)

Standard InChI Key:  NABHHUMHJIHHIX-UHFFFAOYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 461.39

Molecular Weight (Monoisotopic): 460.1433

AlogP: 3.78

#Rotatable Bonds: 7

Polar Surface Area: 71.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 6.95

CX LogP: 3.46

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -1.19

References

1. Newman AH, Grundt P, Cyriac G, Deschamps JR, Taylor M, Kumar R, Ho D, Luedtke RR..  (2009)  N-(4-(4-(2,3-dichloro- or 2-methoxyphenyl)piperazin-1-yl)butyl)heterobiarylcarboxamides with functionalized linking chains as high affinity and enantioselective D3 receptor antagonists.,  52  (8): [PMID:19331412] [10.1021/jm900095y]

2. Banala AK, Levy BA, Khatri SS, Furman CA, Roof RA, Mishra Y, Griffin SA, Sibley DR, Luedtke RR, Newman AH..  (2011)  N-(3-fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl)arylcarboxamides as selective dopamine D3 receptor ligands: critical role of the carboxamide linker for D3 receptor selectivity.,  54  (10): [PMID:21495689] [10.1021/jm200288r]

3. Chen J, Levant B, Jiang C, Keck TM, Newman AH, Wang S..  (2014)  Tranylcypromine substituted cis-hydroxycyclobutylnaphthamides as potent and selective dopamine D₃ receptor antagonists.,  57  (11): [PMID:24848155] [10.1021/jm401798r]

4. Kumar V, Banala AK, Garcia EG, Cao J, Keck TM, Bonifazi A, Deschamps JR, Newman AH..  (2014)  Chiral Resolution and Serendipitous Fluorination Reaction for the Selective Dopamine D3 Receptor Antagonist BAK2-66.,  5  (6): [PMID:24944737] [10.1021/ml500006v]

5. Keck TM, Banala AK, Slack RD, Burzynski C, Bonifazi A, Okunola-Bakare OM, Moore M, Deschamps JR, Rais R, Slusher BS, Newman AH..  (2015)  Using click chemistry toward novel 1,2,3-triazole-linked dopamine D3 receptor ligands.,  23  (14): [PMID:25650314] [10.1016/j.bmc.2015.01.017]

6. Keck TM, John WS, Czoty PW, Nader MA, Newman AH..  (2015)  Identifying Medication Targets for Psychostimulant Addiction: Unraveling the Dopamine D3 Receptor Hypothesis.,  58  (14): [PMID:25826710] [10.1021/jm501512b]

7. Boateng CA, Bakare OM, Zhan J, Banala AK, Burzynski C, Pommier E, Keck TM, Donthamsetti P, Javitch JA, Rais R, Slusher BS, Xi ZX, Newman AH..  (2015)  High Affinity Dopamine D3 Receptor (D3R)-Selective Antagonists Attenuate Heroin Self-Administration in Wild-Type but not D3R Knockout Mice.,  58  (15): [PMID:26203768] [10.1021/acs.jmedchem.5b00776]

8.  (2014)  4-phenylpiperazine derivatives with functionalized linkers as dopamine D3 receptor selective ligands and methods of use, 

Source

Source(2):

• Scientific Literature
• BindingDB Database