2-(4-Bromo-phenyl)-N-[3-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-phenyl]-acetamide

ID: ALA2332855

PubChem CID: 71575325

Max Phase: Preclinical

Molecular Formula: C19H14BrN5O2

Molecular Weight: 424.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(Br)cc1)Nc1cccc(Oc2ncnc3[nH]ncc23)c1

Standard InChI:  InChI=1S/C19H14BrN5O2/c20-13-6-4-12(5-7-13)8-17(26)24-14-2-1-3-15(9-14)27-19-16-10-23-25-18(16)21-11-22-19/h1-7,9-11H,8H2,(H,24,26)(H,21,22,23,25)

Standard InChI Key:  MXCDPUJELOTUHB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   18.7387  -18.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4513  -18.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1643  -18.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1617  -19.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4399  -20.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7299  -19.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5789  -20.1015    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2956  -19.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0091  -20.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2987  -18.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4319  -18.8621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4307  -19.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1461  -20.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8632  -19.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8604  -18.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1443  -18.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7153  -20.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7147  -20.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9992  -21.3389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9982  -22.1639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7134  -22.5781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2103  -21.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4287  -21.3378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4336  -22.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2191  -22.4101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6970  -21.7392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8807  -18.4661    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:

   

   ALA2332855

   2-(4-bromophenyl)-N-[3-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]acetamide

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): 423.0331

AlogP: 4.09

#Rotatable Bonds: 5

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: 3.68

CX LogD: 3.63

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.50

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