1-phenyl-4-((1-phenyl-1H-pyrazol-4-yl)methyl)piperazine

ID: ALA210405

Cas Number: 868160-02-5

PubChem CID: 10403608

Max Phase: Preclinical

Molecular Formula: C20H22N4

Molecular Weight: 318.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc(N2CCN(Cc3cnn(-c4ccccc4)c3)CC2)cc1

Standard InChI:  InChI=1S/C20H22N4/c1-3-7-19(8-4-1)23-13-11-22(12-14-23)16-18-15-21-24(17-18)20-9-5-2-6-10-20/h1-10,15,17H,11-14,16H2

Standard InChI Key:  PMMMMZICRVMUKQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -0.6603   -3.9110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808   -3.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -3.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315   -2.4037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5110   -2.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -3.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6670   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    0.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -0.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3571   -0.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1821   -0.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370   -0.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    1.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841    1.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4841    2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696    2.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0551    1.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3248   -4.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4957   -4.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8312   -5.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3463   -6.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4742   -6.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097   -5.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  8  9  1  0
  9 10  2  0
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 11 12  2  0
  8 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 18  2  0
  8 13  1  0
  7 11  1  0
  4  7  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
  1 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA210405

   1-Phenyl-4-[(1-phenyl-1H-pyrazol-4-yl)methyl]piperazine

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: 318.42

Molecular Weight (Monoisotopic): 318.1844

AlogP: 3.19

#Rotatable Bonds: 4

Polar Surface Area: 24.30

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.05

CX LogP: 3.74

CX LogD: 3.58

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -1.97

References

1. Löber S, Hübner H, Gmeiner P..  (2006)  Synthesis and biological investigations of dopaminergic partial agonists preferentially recognizing the D4 receptor subtype.,  16  (11): [PMID:16563764] [10.1016/j.bmcl.2006.02.075]

2. Salama I, Hocke C, Utz W, Prante O, Boeckler F, Hübner H, Kuwert T, Gmeiner P..  (2007)  Structure-selectivity investigations of D2-like receptor ligands by CoMFA and CoMSIA guiding the discovery of D3 selective PET radioligands.,  50  (3): [PMID:17266201] [10.1021/jm0611152]

3. Neves G, Menegatti R, Antonio CB, Grazziottin LR, Vieira RO, Rates SM, Noël F, Barreiro EJ, Fraga CA..  (2010)  Searching for multi-target antipsychotics: Discovery of orally active heterocyclic N-phenylpiperazine ligands of D2-like and 5-HT1A receptors.,  18  (5): [PMID:20153652] [10.1016/j.bmc.2010.01.040]

4. Sanna F, Ortner B, Hübner H, Löber S, Tschammer N, Gmeiner P..  (2013)  Discovery of dopamine D₄ receptor antagonists with planar chirality.,  21  (7): [PMID:23428965] [10.1016/j.bmc.2013.01.065]

Source

Source(1):

• Scientific Literature