4-(4-(1H-imidazol-1-yl)phenyl)-6-(3,4-dimethoxyphenyl)-pyrimidin-2-amine

ID: ALA2296867

PubChem CID: 76334874

Max Phase: Preclinical

Molecular Formula: C20H17N5O3

Molecular Weight: 375.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2cc(-c3ccc(-n4ccnc4)cc3)nc(N)n2)ccc1OO

Standard InChI:  InChI=1S/C20H17N5O3/c1-27-19-10-14(4-7-18(19)28-26)17-11-16(23-20(21)24-17)13-2-5-15(6-3-13)25-9-8-22-12-25/h2-12,26H,1H3,(H2,21,23,24)

Standard InChI Key:  HBVCQMATKYFCRM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    3.9648   -9.1046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9637   -9.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6717  -10.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3814   -9.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3786   -9.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700   -8.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611   -8.6920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1754   -7.8793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3760   -7.7096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676   -8.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5146   -9.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0898  -10.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0862  -11.1487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7937  -11.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5018  -11.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4978  -10.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7898   -9.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7946  -12.3733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1986   -9.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9086  -10.3213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6138   -9.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6101   -9.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8953   -8.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1931   -9.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3151   -8.6786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0254   -9.0827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3234  -10.3151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3271  -11.1323    0.0000 C   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
 22 25  1  0
 25 26  1  0
 21 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2296867

   4-(4-Hydroperoxy-3-methoxyphenyl)-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: 375.39

Molecular Weight (Monoisotopic): 375.1331

AlogP: 3.44

#Rotatable Bonds: 5

Polar Surface Area: 108.31

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.47

CX Basic pKa: 6.06

CX LogP: 3.19

CX LogD: 3.17

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -0.79

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