5-[1-(2,4-difluorophenyl)pyrazolo[3,4-b]pyridin-4-yl]pyrimidin-4-amine

ID: ALA5282485

Max Phase: Preclinical

Molecular Formula: C16H10F2N6

Molecular Weight: 324.29

Names and Identifiers

Canonical SMILES:  Nc1ncncc1-c1ccnc2c1cnn2-c1ccc(F)cc1F

Standard InChI:  InChI=1S/C16H10F2N6/c17-9-1-2-14(13(18)5-9)24-16-12(7-23-24)10(3-4-21-16)11-6-20-8-22-15(11)19/h1-8H,(H2,19,20,22)

Standard InChI Key:  GDCKYRZIPLGNHK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -1.5420    1.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5435    0.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2587   -0.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -0.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1145    0.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    1.0765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8267    1.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5029   -0.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709   -1.0546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -0.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5138    0.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3088    0.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    0.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6815   -0.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8861   -0.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6896    0.5319    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2603   -0.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9757   -1.3935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6896   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6881   -0.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9727    0.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9727    1.0821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6725   -1.4903    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  1  1  0
  5  8  1  0
  8  9  1  0
 10  9  2  0
  4 10  1  0
  8 11  1  0
 12 11  2  0
 13 12  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 11 16  1  0
 14 17  1  0
 18  3  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
  3 22  1  0
 22 23  1  0
 16 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282485

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 324.29

Molecular Weight (Monoisotopic): 324.0935

AlogP: 2.74

#Rotatable Bonds: 2

Polar Surface Area: 82.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.17

CX LogP: 2.00

CX LogD: 2.00

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -1.68

References

1. Padmakar Darne C, Velaparthi U, Saulnier M, Frennesson D, Liu P, Huang A, Tokarski J, Fura A, Spires T, Newitt J, Spires VM, Obermeier MT, Elzinga PA, Gottardis MM, Jayaraman L, Vite GD, Balog A..  (2022)  The discovery of BMS-737 as a potent, CYP17 lyase-selective inhibitor for the treatment of castration-resistant prostate cancer.,  75  [PMID:36031020] [10.1016/j.bmcl.2022.128951]

Source

Source(1):

• Scientific Literature