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

ID: ALA2332842

PubChem CID: 71575113

Max Phase: Preclinical

Molecular Formula: C18H14BrN7O

Molecular Weight: 424.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Br)cc1)Nc1ccc(Nc2ncnc3[nH]ncc23)cc1

Standard InChI:  InChI=1S/C18H14BrN7O/c19-11-1-3-13(4-2-11)24-18(27)25-14-7-5-12(6-8-14)23-16-15-9-22-26-17(15)21-10-20-16/h1-10H,(H2,24,25,27)(H2,20,21,22,23,26)

Standard InChI Key:  JWEDGONIPHOTHT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   14.3658   -2.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3646   -2.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0801   -3.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7972   -2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7943   -2.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0783   -1.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5079   -1.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2246   -2.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9382   -1.7440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2277   -2.9854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6548   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6548   -2.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3706   -3.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0852   -2.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0794   -2.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3630   -1.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6492   -3.4090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6486   -4.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9330   -4.6456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9320   -5.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6473   -5.8848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1443   -4.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3626   -4.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3675   -5.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1531   -5.7168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6311   -5.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8024   -3.3825    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:

   

   ALA2332842

   1-(4-bromophenyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)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: 424.26

Molecular Weight (Monoisotopic): 423.0443

AlogP: 4.50

#Rotatable Bonds: 4

Polar Surface Area: 107.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: 2.97

CX LogP: 3.69

CX LogD: 3.68

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: -1.62

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