4-Amino-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide

ID: ALA326753

PubChem CID: 44340726

Max Phase: Preclinical

Molecular Formula: C23H20N6O

Molecular Weight: 396.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)c2ccc(N)cc2)cc1Nc1nccc(-c2cccnc2)n1

Standard InChI:  InChI=1S/C23H20N6O/c1-15-4-9-19(27-22(30)16-5-7-18(24)8-6-16)13-21(15)29-23-26-12-10-20(28-23)17-3-2-11-25-14-17/h2-14H,24H2,1H3,(H,27,30)(H,26,28,29)

Standard InChI Key:  QSOMBOJKYIKONR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    3.6167    0.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -0.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    0.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2125    0.8958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7667    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000    0.8708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    2.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -1.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167    2.1333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -2.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    2.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    2.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375    3.3833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792    3.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    2.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1792   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  5  1  0
  5  1  1  0
  6 11  1  0
  7  2  2  0
  8  4  1  0
  9  1  2  0
 10  3  1  0
 11  8  2  0
 12  7  1  0
 13  4  2  0
 14  3  2  0
 15 26  2  0
 16 10  2  0
 17 10  1  0
 18 13  1  0
 19 20  2  0
 20  9  1  0
 21 25  1  0
 22 18  2  0
 23 21  1  0
 24 16  1  0
 25 17  2  0
 26 12  1  0
 27 12  2  0
 28 30  2  0
 29 13  1  0
 30 27  1  0
 19  7  1  0
 22 11  1  0
 28 15  1  0
 24 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA326753

   4-amino-N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)benzamide

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: 396.45

Molecular Weight (Monoisotopic): 396.1699

AlogP: 4.43

#Rotatable Bonds: 5

Polar Surface Area: 105.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.69

CX Basic pKa: 4.28

CX LogP: 3.76

CX LogD: 3.76

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: -1.67

References

1. Rachid Z, Katsoulas A, Brahimi F, Jean-Claude BJ..  (2003)  Synthesis of pyrimidinopyridine-triazene conjugates targeted to abl tyrosine kinase.,  13  (19): [PMID:12951113] [10.1016/s0960-894x(03)00553-5]

2. Rachid Z, Katsoulas A, Williams C, Larroque AL, McNamee J, Jean-Claude BJ..  (2007)  Optimization of novel combi-molecules: identification of balanced and mixed bcr-abl/DNA targeting properties.,  17  (15): [PMID:17572088] [10.1016/j.bmcl.2007.05.067]

3. Lü S, Luo Q, Hao X, Li X, Ji L, Zheng W, Wang F..  (2011)  Synthesis and docking study of 2-phenylaminopyrimidine Abl tyrosine kinase inhibitors.,  21  (23): [PMID:22033461] [10.1016/j.bmcl.2011.09.127]

4. Cui J, Fu R, Zhou LH, Chen SP, Li GW, Qian SX, Liu S..  (2013)  BCR-ABL tyrosine kinase inhibitor pharmacophore model derived from a series of phenylaminopyrimidine-based (PAP) derivatives.,  23  (8): [PMID:23473682] [10.1016/j.bmcl.2013.01.113]

Source

Source(1):

• Scientific Literature