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

ID: ALA2332854

PubChem CID: 71575324

Max Phase: Preclinical

Molecular Formula: C20H14F3N5O2

Molecular Weight: 413.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H14F3N5O2/c21-20(22,23)13-6-4-12(5-7-13)8-17(29)27-14-2-1-3-15(9-14)30-19-16-10-26-28-18(16)24-11-25-19/h1-7,9-11H,8H2,(H,27,29)(H,24,25,26,28)

Standard InChI Key:  IHEVLQKGFWWIEI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    8.5728  -18.4831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2849  -18.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9973  -18.4860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9946  -19.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2736  -19.7216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5641  -19.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4149  -19.7099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1309  -19.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8439  -19.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1340  -18.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696  -18.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684  -19.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9833  -19.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6998  -19.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6969  -18.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815  -18.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536  -19.7109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5530  -20.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380  -20.9463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370  -21.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5518  -22.1845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0474  -20.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664  -20.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2712  -21.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562  -22.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5337  -21.3463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7131  -18.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4263  -18.4907    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.7159  -17.2508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.4255  -17.6591    0.0000 F   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
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332854

   N-[3-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl]-2-[4-(trifluoromethyl)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: 413.36

Molecular Weight (Monoisotopic): 413.1100

AlogP: 4.35

#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: 3.78

CX LogD: 3.74

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -2.00

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