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

ID: ALA2332848

PubChem CID: 71575212

Max Phase: Preclinical

Molecular Formula: C20H18N6O2

Molecular Weight: 374.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(NC(=O)Nc2ccc(Oc3ncnc4[nH]ncc34)cc2)c1C

Standard InChI:  InChI=1S/C20H18N6O2/c1-12-4-3-5-17(13(12)2)25-20(27)24-14-6-8-15(9-7-14)28-19-16-10-23-26-18(16)21-11-22-19/h3-11H,1-2H3,(H2,24,25,27)(H,21,22,23,26)

Standard InChI Key:  XGSWZLFJJSMWPI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.5382  -11.2554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5371  -12.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2522  -12.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9690  -12.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9662  -11.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2504  -10.8424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6794  -10.8363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3958  -11.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1090  -10.8309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3989  -12.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8254  -11.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8254  -12.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5409  -12.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2551  -12.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2494  -11.2300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5332  -10.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220  -12.4953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213  -13.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1061  -13.7312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1051  -14.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8201  -14.9699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3163  -13.4723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351  -13.7301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5399  -14.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3251  -14.8020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8030  -14.1313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5265   -9.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9611  -10.8122    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:

   

   ALA2332848

   1-(2,3-dimethylphenyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)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: 374.40

Molecular Weight (Monoisotopic): 374.1491

AlogP: 4.41

#Rotatable Bonds: 4

Polar Surface Area: 104.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 1.37

CX LogP: 4.01

CX LogD: 3.97

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -2.00

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