1-(4-(1H-Pyrazolo[3,4-d]pyrimidin-4-yloxy)-2-fluorophenyl)-3-(5-tert-butylisoxazol-3-yl)urea

ID: ALA4514229

PubChem CID: 118489453

Max Phase: Preclinical

Molecular Formula: C19H18FN7O3

Molecular Weight: 411.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(NC(=O)Nc2ccc(Oc3ncnc4[nH]ncc34)cc2F)no1

Standard InChI:  InChI=1S/C19H18FN7O3/c1-19(2,3)14-7-15(27-30-14)25-18(28)24-13-5-4-10(6-12(13)20)29-17-11-8-23-26-16(11)21-9-22-17/h4-9H,1-3H3,(H,21,22,23,26)(H2,24,25,27,28)

Standard InChI Key:  AVISKTSTUQBYGH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   11.2126  -17.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2185  -17.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9370  -16.7080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6454  -17.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4014  -16.7964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9492  -17.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5337  -18.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8609  -18.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7241  -17.9443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5060  -16.6948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7917  -17.1013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0791  -16.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0849  -15.8594    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3606  -17.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7816  -17.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0632  -18.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3547  -17.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6363  -18.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6304  -19.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388  -19.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3329  -20.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1159  -20.6510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6071  -19.9895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1281  -19.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6145  -20.7959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060  -20.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9120  -19.5540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3691  -19.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6804  -18.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1886  -19.6390    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  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  4  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  2  0
 15 16  1  0
 16 17  2  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 20 24  1  0
 21 25  2  0
 25 26  1  0
 26 27  2  0
 19 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514229

   1-(5-tert-butyl-1,2-oxazol-3-yl)-3-[2-fluoro-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: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 411.40

Molecular Weight (Monoisotopic): 411.1455

AlogP: 4.21

#Rotatable Bonds: 4

Polar Surface Area: 130.85

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.02

CX Basic pKa: 1.19

CX LogP: 3.55

CX LogD: 3.45

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.46

Np Likeness Score: -2.24

References

1. Li GB, Ma S, Yang LL, Ji S, Fang Z, Zhang G, Wang LJ, Zhong JM, Xiong Y, Wang JH, Huang SZ, Li LL, Xiang R, Niu D, Chen YC, Yang SY..  (2016)  Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model.,  59  (18): [PMID:27535613] [10.1021/acs.jmedchem.6b00604]

Source

Source(1):

• Scientific Literature