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

ID: ALA2332852

PubChem CID: 71575322

Max Phase: Preclinical

Molecular Formula: C19H13F3N6O2

Molecular Weight: 414.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(C(F)(F)F)cc1)Nc1cccc(Oc2ncnc3[nH]ncc23)c1

Standard InChI:  InChI=1S/C19H13F3N6O2/c20-19(21,22)11-4-6-12(7-5-11)26-18(29)27-13-2-1-3-14(8-13)30-17-15-9-25-28-16(15)23-10-24-17/h1-10H,(H2,26,27,29)(H,23,24,25,28)

Standard InChI Key:  DUAXMDPWOSWFOO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    7.8875  -11.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6001  -11.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3131  -11.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3104  -12.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5888  -13.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8787  -12.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7278  -13.0034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4444  -12.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1579  -13.0088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4475  -11.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808  -11.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5796  -12.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950  -13.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0120  -12.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0092  -11.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2932  -11.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642  -13.0044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8635  -13.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1480  -14.2408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470  -15.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8623  -15.4800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3592  -13.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5776  -14.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5824  -15.0634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3680  -15.3120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8459  -14.6411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0295  -11.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7433  -11.7833    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0323  -10.5424    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7424  -10.9509    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  1  0
  8  9  1  0
  8 10  2  0
  9  6  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
 12 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
 14  7  1  0
  3 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332852

   1-[3-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]-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: 414.35

Molecular Weight (Monoisotopic): 414.1052

AlogP: 4.81

#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: 3.86

CX LogD: 3.82

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.44

Np Likeness Score: -1.98

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