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

ID: ALA2332857

PubChem CID: 71575327

Max Phase: Preclinical

Molecular Formula: C18H12BrN5O2

Molecular Weight: 410.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cccc(Oc2ncnc3[nH]ncc23)c1)c1ccc(Br)cc1

Standard InChI:  InChI=1S/C18H12BrN5O2/c19-12-6-4-11(5-7-12)17(25)23-13-2-1-3-14(8-13)26-18-15-9-22-24-16(15)20-10-21-18/h1-10H,(H,23,25)(H,20,21,22,24)

Standard InChI Key:  CAKCWVMJYXCZCX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   17.3318  -27.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0445  -26.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7576  -27.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7549  -28.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0332  -28.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3230  -28.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9014  -27.3114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6181  -26.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6212  -26.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7540  -26.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7528  -26.9001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4684  -27.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1855  -26.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1827  -26.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4666  -25.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0373  -27.3124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0367  -28.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3211  -28.5491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3200  -29.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0354  -29.7884    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5326  -28.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7508  -28.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7557  -29.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5414  -29.6205    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0194  -28.9494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4680  -28.5630    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  2  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 11 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 23  1  0
 22 17  1  0
 22 23  2  0
 21 22  1  0
 23 24  1  0
 24 25  1  0
 25 21  2  0
 13  7  1  0
  8  1  1  0
  4 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332857

   4-bromo-N-[3-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]benzamide

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: 410.23

Molecular Weight (Monoisotopic): 409.0174

AlogP: 4.16

#Rotatable Bonds: 4

Polar Surface Area: 92.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 1.37

CX LogP: 3.70

CX LogD: 3.65

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: -1.97

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