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

ID: ALA2332847

PubChem CID: 71575211

Max Phase: Preclinical

Molecular Formula: C18H13BrN6O2

Molecular Weight: 425.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H13BrN6O2/c19-11-1-3-12(4-2-11)23-18(26)24-13-5-7-14(8-6-13)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:  ZDABLTOZCXSNEA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   15.6086   -4.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6075   -4.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3229   -5.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0401   -4.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0371   -4.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3211   -3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7507   -3.5886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4674   -3.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1810   -3.5831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4705   -4.8245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8976   -3.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8976   -4.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6134   -5.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3280   -4.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3223   -3.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6058   -3.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8920   -5.2482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8914   -6.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1758   -6.4847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1748   -7.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8902   -7.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3871   -6.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6054   -6.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6102   -7.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3959   -7.5559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8738   -6.8850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0453   -5.2216    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
  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
 14 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332847

   1-(4-bromophenyl)-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: 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: -1.65

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