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

ID: ALA2332851

PubChem CID: 71575215

Max Phase: Preclinical

Molecular Formula: C20H15F3N6O2

Molecular Weight: 428.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1ncc2c(Oc3ccc(NC(=O)Nc4ccc(C(F)(F)F)cc4)cc3)ncnc21

Standard InChI:  InChI=1S/C20H15F3N6O2/c1-29-17-16(10-26-29)18(25-11-24-17)31-15-8-6-14(7-9-15)28-19(30)27-13-4-2-12(3-5-13)20(21,22)23/h2-11H,1H3,(H2,27,28,30)

Standard InChI Key:  JIWVARRTFYLYOQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   19.3585   -5.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0711   -5.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7842   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7814   -4.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0598   -3.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3498   -4.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0569   -4.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0558   -5.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7712   -5.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4883   -5.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4853   -4.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7694   -3.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1989   -3.9052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9154   -4.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6290   -3.8998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9186   -5.1411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3404   -5.5648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3397   -6.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6242   -6.8011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6232   -7.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3385   -8.0403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8353   -6.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0537   -6.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0585   -7.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8441   -7.8723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3220   -7.2014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1059   -8.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5005   -5.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5033   -6.3662    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.2143   -5.1253    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.2101   -5.9508    0.0000 F   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
 23 24  2  0
 22 23  1  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
 25 27  1  0
  3 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332851

   1-[4-(1-Methylpyrazolo[3,4-d]pyrimidin-4-yl)oxyphenyl]-3-[4-(trifluoromethyl)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: 428.37

Molecular Weight (Monoisotopic): 428.1209

AlogP: 4.82

#Rotatable Bonds: 4

Polar Surface Area: 93.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.62

CX Basic pKa: 0.96

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: -1.81

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