1-(2,3-Dimethyl-phenyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-phenyl]-urea

ID: ALA2332843

PubChem CID: 71575114

Max Phase: Preclinical

Molecular Formula: C20H19N7O

Molecular Weight: 373.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(NC(=O)Nc2ccc(Nc3ncnc4[nH]ncc34)cc2)c1C

Standard InChI:  InChI=1S/C20H19N7O/c1-12-4-3-5-17(13(12)2)26-20(28)25-15-8-6-14(7-9-15)24-18-16-10-23-27-19(16)22-11-21-18/h3-11H,1-2H3,(H2,25,26,28)(H2,21,22,23,24,27)

Standard InChI Key:  VWCFFXCKCOGDHF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    3.2960   -9.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949  -10.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0100  -10.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7268  -10.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240   -9.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0082   -9.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4372   -8.9980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1536   -9.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8668   -8.9926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1566  -10.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5832   -9.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5832  -10.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2987  -10.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0129  -10.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0072   -9.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911   -8.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797  -10.6569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5790  -11.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8638  -11.8929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8628  -12.7175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5778  -13.1316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0741  -11.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2928  -11.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977  -12.7151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0829  -12.9637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5607  -12.2931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2843   -8.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7190   -8.9737    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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  2 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 24  1  0
 23 18  1  0
 23 24  2  0
 22 23  1  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
 16 27  1  0
 15 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332843

   1-(2,3-dimethylphenyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)phenyl]urea

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: 373.42

Molecular Weight (Monoisotopic): 373.1651

AlogP: 4.36

#Rotatable Bonds: 4

Polar Surface Area: 107.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: 2.97

CX LogP: 3.95

CX LogD: 3.94

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.43

Np Likeness Score: -1.97

References

1. Yang LL, Li GB, Ma S, Zou C, Zhou S, Sun QZ, Cheng C, Chen X, Wang LJ, Feng S, Li LL, Yang SY..  (2013)  Structure-activity relationship studies of pyrazolo[3,4-d]pyrimidine derivatives leading to the discovery of a novel multikinase inhibitor that potently inhibits FLT3 and VEGFR2 and evaluation of its activity against acute myeloid leukemia in vitro and in vivo.,  56  (4): [PMID:23362959] [10.1021/jm301537p]

Source

Source(1):

• Scientific Literature