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

ID: ALA2332845

PubChem CID: 71575116

Max Phase: Preclinical

Molecular Formula: C20H19N7O

Molecular Weight: 373.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(NC(=O)Nc1ccc(Nc2ncnc3[nH]ncc23)cc1)c1ccccc1

Standard InChI:  InChI=1S/C20H19N7O/c1-13(14-5-3-2-4-6-14)24-20(28)26-16-9-7-15(8-10-16)25-18-17-11-23-27-19(17)22-12-21-18/h2-13H,1H3,(H2,24,26,28)(H2,21,22,23,25,27)

Standard InChI Key:  PWXYTXQUAQRJAT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    3.6378  -17.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6366  -18.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3518  -18.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685  -18.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0657  -17.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500  -17.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7788  -17.2183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4953  -17.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2085  -17.2129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4984  -18.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9248  -17.6229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9215  -18.8771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9208  -19.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056  -20.1131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2046  -20.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9196  -21.3518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159  -19.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6346  -20.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6394  -20.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247  -21.1839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9024  -20.5133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9280  -18.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6381  -17.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3504  -17.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0632  -17.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0605  -16.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3391  -15.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6293  -16.3855    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:

   

   ALA2332845

   1-(1-phenylethyl)-3-[4-(1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)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: 373.42

Molecular Weight (Monoisotopic): 373.1651

AlogP: 3.98

#Rotatable Bonds: 5

Polar Surface Area: 107.62

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: 2.98

CX LogP: 3.04

CX LogD: 3.03

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.85

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