4-(3,methylhydroxy3-methyltriaz-1-ene)-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)-phenyl]-benzamide

ID: ALA230286

PubChem CID: 9982070

Max Phase: Preclinical

Molecular Formula: C25H24N8O2

Molecular Weight: 468.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H24N8O2/c1-17-5-8-21(28-24(35)18-6-9-20(10-7-18)31-32-33(2)16-34)14-23(17)30-25-27-13-11-22(29-25)19-4-3-12-26-15-19/h3-15,34H,16H2,1-2H3,(H,28,35)(H,27,29,30)

Standard InChI Key:  CRNMRKUVIVTISX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   14.8642    2.5306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5801    2.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2932    2.5352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5828    1.2954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8675    0.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8698    0.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5862   -0.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3017    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2958    0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8736    2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8724    1.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5872    0.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3037    1.2648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3008    2.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5854    2.5045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0137    2.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7297    2.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7295    1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4447    0.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1586    1.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1528    2.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4370    2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0156    0.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5889    0.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8727   -0.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8722   -1.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5871   -1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3040   -1.2040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3010   -0.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5900   -1.1777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5833   -2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5792   -2.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8626   -3.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2915   -3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2874   -4.0661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0
 17 18  2  0
  9  4  1  0
 18 19  1  0
  4  5  2  0
 19 20  2  0
  2  3  2  0
 20 21  1  0
 10 11  2  0
 21 22  2  0
 22 17  1  0
  5  6  1  0
 18 23  1  0
 21  1  1  0
 11 12  1  0
  1  2  1  0
 24 25  2  0
 12 13  2  0
 25 26  1  0
  6  7  2  0
 26 27  2  0
 13 14  1  0
 27 28  1  0
  2  4  1  0
 28 29  2  0
 29 24  1  0
 12 24  1  0
 14 15  2  0
  7 30  1  0
 15 10  1  0
 30 31  2  3
  7  8  1  0
 31 32  1  0
 14 16  1  0
 32 33  1  0
 32 34  1  0
 16 17  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA230286

   4-(3,methylhydroxy3-methyltriaz-1-ene)-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: 468.52

Molecular Weight (Monoisotopic): 468.2022

AlogP: 4.72

#Rotatable Bonds: 8

Polar Surface Area: 127.99

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.64

CX Basic pKa: 4.26

CX LogP: 4.40

CX LogD: 4.40

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: -1.58

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. 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