1-(3-tert-Butyl-1-m-tolyl-1H-pyrazol-5-yl)-3-(4-(6-nitroquinazolin-4-ylamino)phenyl)urea

ID: ALA526930

PubChem CID: 44186373

Max Phase: Preclinical

Molecular Formula: C29H28N8O3

Molecular Weight: 536.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(-n2nc(C(C)(C)C)cc2NC(=O)Nc2ccc(Nc3ncnc4ccc([N+](=O)[O-])cc34)cc2)c1

Standard InChI:  InChI=1S/C29H28N8O3/c1-18-6-5-7-21(14-18)36-26(16-25(35-36)29(2,3)4)34-28(38)33-20-10-8-19(9-11-20)32-27-23-15-22(37(39)40)12-13-24(23)30-17-31-27/h5-17H,1-4H3,(H,30,31,32)(H2,33,34,38)

Standard InChI Key:  DMZNDLZAGFMTCP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 44  0  0  0  0  0  0  0  0999 V2000
    3.3490    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1349    1.2550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6206    0.5870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1316   -0.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492    0.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1481   -0.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8716   -1.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4413   -1.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9415   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6810    1.4874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    1.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509    1.4987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9572    0.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5326    1.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8958    1.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9023    0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1850   -0.1421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298    0.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6200   -0.1327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6248   -0.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6347   -2.6052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9146   -2.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9129   -1.3683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3480   -2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3389   -1.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0443   -0.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7593   -1.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7645   -2.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0585   -2.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4697   -0.9284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -1.3355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4630   -0.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5451    1.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685    1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7786    2.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3627    3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5326    3.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1262    2.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6045    2.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
 17 20  1  0
  1 10  1  0
 20 21  1  0
 21 26  2  0
  5  1  2  0
 25 22  2  0
 10 11  1  0
 22 23  1  0
  1  2  1  0
 23 24  2  0
 24 21  1  0
 11 12  1  0
  4  6  1  0
 25 26  1  0
 11 13  2  0
 26 27  1  0
 27 28  2  0
 12 14  1  0
 28 29  1  0
  6  7  1  0
 29 30  2  0
 30 25  1  0
 14 15  2  0
  2  3  1  0
 15 16  1  0
 31 32  2  0
 31 33  1  0
 28 31  1  0
  6  8  1  0
  2 34  1  0
 16 17  2  0
 34 35  2  0
  3  4  2  0
 35 36  1  0
 17 18  1  0
 36 37  2  0
  6  9  1  0
 37 38  1  0
 18 19  2  0
 38 39  2  0
 39 34  1  0
 19 14  1  0
 36 40  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA526930

   1-[5-Tert-butyl-2-(3-methylphenyl)pyrazol-3-yl]-3-[4-[(6-nitroquinazolin-4-yl)amino]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: 536.60

Molecular Weight (Monoisotopic): 536.2284

AlogP: 6.72

#Rotatable Bonds: 6

Polar Surface Area: 139.90

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.57

CX Basic pKa: 3.19

CX LogP: 7.16

CX LogD: 7.16

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.16

Np Likeness Score: -1.99

References

1. Getlik M, Grütter C, Simard JR, Klüter S, Rabiller M, Rode HB, Robubi A, Rauh D..  (2009)  Hybrid compound design to overcome the gatekeeper T338M mutation in cSrc.,  52  (13): [PMID:19462975] [10.1021/jm9002928]

2. Klüter S, Grütter C, Naqvi T, Rabiller M, Simard JR, Pawar V, Getlik M, Rauh D..  (2010)  Displacement assay for the detection of stabilizers of inactive kinase conformations.,  53  (1): [PMID:19928858] [10.1021/jm901297e]

Source

Source(1):

• Scientific Literature