4-(4-(1H-imidazol-1-yl)phenyl)-6-(2,4-dichlorophenyl)-pyrimidin-2-amine

ID: ALA2296868

PubChem CID: 76331288

Max Phase: Preclinical

Molecular Formula: C19H13Cl2N5

Molecular Weight: 382.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(-c2ccc(-n3ccnc3)cc2)cc(-c2ccc(Cl)cc2Cl)n1

Standard InChI:  InChI=1S/C19H13Cl2N5/c20-13-3-6-15(16(21)9-13)18-10-17(24-19(22)25-18)12-1-4-14(5-2-12)26-8-7-23-11-26/h1-11H,(H2,22,24,25)

Standard InChI Key:  CODAQZKCYATQDP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   13.4657   -9.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4646  -10.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1726  -10.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8823  -10.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8795   -9.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1708   -8.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7619   -8.8158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6763   -8.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8769   -7.8334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4685   -8.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0155   -9.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5906  -10.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5871  -11.2725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2946  -11.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0026  -11.2702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9987  -10.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2906  -10.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2955  -12.4971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6994  -10.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4095  -10.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1147  -10.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1109   -9.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3962   -8.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6940   -9.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4128  -11.2623    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.8160   -8.8024    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
  1  7  1  0
  4 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 14 18  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 16 19  1  0
 20 25  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296868

   4-(2,4-Dichlorophenyl)-6-(4-imidazol-1-ylphenyl)pyrimidin-2-amine

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: 382.25

Molecular Weight (Monoisotopic): 381.0548

AlogP: 4.89

#Rotatable Bonds: 3

Polar Surface Area: 69.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.05

CX LogP: 4.94

CX LogD: 4.92

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -1.76

References

1. Bukhari MH, Ahmad M, Hussain T, Umar S, Ahmad N.  (2013)  Synthesis and biological studies of a novel series of 4-(4-(1H-imidazol-1-yl)phenyl)-6-arylpyrimidin-2-amines,  22  (11): [10.1007/s00044-013-0523-6]

Source

Source(1):

• Scientific Literature