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

ID: ALA2332871

PubChem CID: 71575641

Max Phase: Preclinical

Molecular Formula: C19H12ClF3N6O2

Molecular Weight: 448.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Oc2ncnc3[nH]ncc23)cc1)Nc1ccc(C(F)(F)F)cc1Cl

Standard InChI:  InChI=1S/C19H12ClF3N6O2/c20-14-7-10(19(21,22)23)1-6-15(14)28-18(30)27-11-2-4-12(5-3-11)31-17-13-8-26-29-16(13)24-9-25-17/h1-9H,(H2,27,28,30)(H,24,25,26,29)

Standard InChI Key:  GTISFBOEAJPQNU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.7196   -4.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4322   -5.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1453   -4.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1425   -3.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4209   -3.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7109   -3.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4181   -4.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4169   -4.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1323   -5.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8494   -4.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8464   -4.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1305   -3.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5600   -3.5883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2766   -3.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9901   -3.5828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2797   -4.8241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015   -5.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009   -6.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9853   -6.4842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9844   -7.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997   -7.7233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1965   -6.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4149   -6.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4197   -7.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2052   -7.5553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6832   -6.8844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8616   -5.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8644   -6.0492    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5754   -4.8084    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5712   -5.6338    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.4149   -2.7509    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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15  6  1  0
  8 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
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 22 23  1  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
  3 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  5 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332871

   1-[2-chloro-4-(trifluoromethyl)phenyl]-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: 448.79

Molecular Weight (Monoisotopic): 448.0662

AlogP: 5.46

#Rotatable Bonds: 4

Polar Surface Area: 104.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.39

CX Basic pKa: 1.37

CX LogP: 4.46

CX LogD: 4.42

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -2.18

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