1-(1-Phenyl-ethyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-phenyl]-urea

ID: ALA2332862

PubChem CID: 71718823

Max Phase: Preclinical

Molecular Formula: C20H18N6O2

Molecular Weight: 374.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(NC(=O)Nc1ccc(Oc2ncnc3[nH]ncc23)cc1)c1ccccc1

Standard InChI:  InChI=1S/C20H18N6O2/c1-13(14-5-3-2-4-6-14)24-20(27)25-15-7-9-16(10-8-15)28-19-17-11-23-26-18(17)21-12-22-19/h2-13H,1H3,(H2,24,25,27)(H,21,22,23,26)

Standard InChI Key:  MIWZYZZIWMTBTD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.8800  -19.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8788  -20.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940  -20.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3107  -20.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3078  -19.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5921  -19.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0211  -19.0564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7374  -19.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4507  -19.0511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7405  -20.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1670  -19.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1637  -20.7153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1630  -21.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478  -21.9512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468  -22.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1618  -23.1899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6581  -21.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8767  -21.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8816  -22.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6669  -23.0220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1446  -22.3514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1701  -20.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8803  -19.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5925  -19.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3053  -19.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3027  -18.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5813  -17.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8715  -18.2238    0.0000 C   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
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 19  1  0
 18 13  1  0
 18 19  2  0
 17 18  1  0
 19 20  1  0
 20 21  1  0
 21 17  2  0
 11 22  1  0
 11 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2332862

   1-(1-phenylethyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)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: 374.40

Molecular Weight (Monoisotopic): 374.1491

AlogP: 4.03

#Rotatable Bonds: 5

Polar Surface Area: 104.82

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.39

CX Basic pKa: 1.37

CX LogP: 3.10

CX LogD: 3.06

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -1.88

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