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

ID: ALA2332859

PubChem CID: 71575437

Max Phase: Preclinical

Molecular Formula: C19H14BrN5O2

Molecular Weight: 424.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Cc1ccc(Br)cc1)Nc1ccc(Oc2ncnc3[nH]ncc23)cc1

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

Standard InChI Key:  RGMYTZVNRAGGPE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   19.8750   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5876   -4.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3005   -4.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2979   -3.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5763   -2.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8663   -3.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7156   -2.9348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4321   -3.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1456   -2.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4352   -4.1706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5729   -3.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5717   -4.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2871   -4.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0040   -4.1800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0012   -3.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2853   -2.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8564   -4.5927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8558   -5.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1403   -5.8290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1392   -6.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8545   -7.0681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3512   -5.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5697   -5.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5745   -6.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3600   -6.9001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8379   -6.2292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0169   -4.5700    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
 15  7  1  0
  3 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332859

   2-(4-bromophenyl)-N-[4-(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: -1.81

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