3-{[4-(3,4-Dichlorophenyl)piperazin-1-yl]methyl}-2,5,7-trimethylimidazo[1,2-c]pyrimidine

ID: ALA563078

PubChem CID: 45273442

Max Phase: Preclinical

Molecular Formula: C20H23Cl2N5

Molecular Weight: 404.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2nc(C)c(CN3CCN(c4ccc(Cl)c(Cl)c4)CC3)n2c(C)n1

Standard InChI:  InChI=1S/C20H23Cl2N5/c1-13-10-20-24-14(2)19(27(20)15(3)23-13)12-25-6-8-26(9-7-25)16-4-5-17(21)18(22)11-16/h4-5,10-11H,6-9,12H2,1-3H3

Standard InChI Key:  OPCWNMLUZVXULW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   12.7562   -0.6737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7562   -1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0417   -1.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0417   -0.2612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3272   -0.6737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3272   -1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5426   -1.7537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0577   -1.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5426   -0.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2327   -1.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2877    0.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4807    0.5374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2258    1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4188    1.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8668    0.8804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1217    0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9287   -0.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0598    1.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5078    0.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7008    0.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4459    1.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979    2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8049    1.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4707   -1.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0417    0.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6389    1.5665    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7430    2.7927    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  1  2  1  0
  5  4  1  0
  6  7  2  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
  8  9  2  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  2  0
 20 21  2  0
  8 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
  9 11  1  0
  2 24  1  0
  4 25  1  0
 11 12  1  0
 12 13  1  0
 21 26  1  0
  2  3  2  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA563078

   3-{[4-(3,4-Dichlorophenyl)piperazin-1-yl]methyl}-2,5,7-trimethylimidazo[1,2-c]pyrimidine

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

Calculated Properties

Molecular Weight: 404.35

Molecular Weight (Monoisotopic): 403.1331

AlogP: 4.28

#Rotatable Bonds: 3

Polar Surface Area: 36.67

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.90

CX LogP: 2.75

CX LogD: 2.63

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -1.95

References

1. Linz S, Müller J, Hübner H, Gmeiner P, Troschütz R..  (2009)  Design, synthesis and dopamine D4 receptor binding activities of new N-heteroaromatic 5/6-ring Mannich bases.,  17  (13): [PMID:19481941] [10.1016/j.bmc.2009.05.015]

Source

Source(1):

• Scientific Literature