N-(4-Pyridin-3-yl-pyrimidin-2-yl)-benzene-1,3-diamine

ID: ALA57553

Cas Number: 152460-06-5

PubChem CID: 9943194

Max Phase: Preclinical

Molecular Formula: C15H13N5

Molecular Weight: 263.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1cccc(Nc2nccc(-c3cccnc3)n2)c1

Standard InChI:  InChI=1S/C15H13N5/c16-12-4-1-5-13(9-12)19-15-18-8-6-14(20-15)11-3-2-7-17-10-11/h1-10H,16H2,(H,18,19,20)

Standard InChI Key:  ZQTRXPRIWRFHRY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.2321    4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1603    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2942    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1603    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4282    1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4282    2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5622    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5000    2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2942    0.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    3.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641    2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6962    2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0
  1  5  1  0
  2  3  2  0
  2  7  1  0
  3 11  1  0
  4 12  1  0
  5 13  2  0
  6  8  2  0
  6 14  1  0
  7 17  2  0
  8 18  1  0
  9 12  2  0
  9 13  1  0
 10 11  2  0
 10 17  1  0
 11 14  1  0
 12 16  1  0
 13 19  1  0
 14 20  2  0
 15 18  2  0
 15 19  1  0
 15 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA57553

   N-(3-aminophenyl)-4-(3-pyridyl)-2-pyrimidine-amine

2. Alternative Forms:

   

   ALA57553

   3-N-(4-pyridin-3-ylpyrimidin-2-yl)benzene-1,3-diamine;dihydrochloride

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: 263.30

Molecular Weight (Monoisotopic): 263.1171

AlogP: 2.86

#Rotatable Bonds: 3

Polar Surface Area: 76.72

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.44

CX Basic pKa: 4.67

CX LogP: 2.15

CX LogD: 2.15

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: -1.51

References

1. Zimmermann J, Buchdunger E, Mett H, Meyer T, Lydon NB.  (1997)  Potent and selective inhibitors of the Abl-kinase: phenylamino-pyrimidine (PAP) derivatives,  7  (2): [10.1016/S0960-894X(96)00601-4]

2. 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]

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