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

ID: ALA2332853

PubChem CID: 71575323

Max Phase: Preclinical

Molecular Formula: C18H13BrN6O2

Molecular Weight: 425.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H13BrN6O2/c19-11-4-6-12(7-5-11)23-18(26)24-13-2-1-3-14(8-13)27-17-15-9-22-25-16(15)20-10-21-17/h1-10H,(H2,23,24,26)(H,20,21,22,25)

Standard InChI Key:  APXHFYKTUZWPIJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   18.0470  -12.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7596  -11.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4727  -12.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4700  -12.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7483  -13.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0383  -12.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8872  -13.3794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6039  -12.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3174  -13.3848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6069  -12.1435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7401  -12.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7389  -12.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4543  -13.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1715  -12.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1685  -12.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4525  -11.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0234  -13.3804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0228  -14.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3072  -14.6169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3062  -15.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0216  -15.8562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5185  -14.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7368  -14.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7417  -15.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5273  -15.6881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0053  -15.0172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1891  -11.7440    0.0000 Br  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
M  END

Alternative Forms

1. Parent:

   

   ALA2332853

   1-(4-bromophenyl)-3-[3-(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: 425.25

Molecular Weight (Monoisotopic): 424.0283

AlogP: 4.55

#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: 3.75

CX LogD: 3.71

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -1.96

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