5-Chloro-N2-(4-chloropyridin-2-yl)-N4-(o-tolyl)pyrimidine-2,4-diamine

ID: ALA4644616

PubChem CID: 155665844

Max Phase: Preclinical

Molecular Formula: C16H13Cl2N5

Molecular Weight: 346.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccccc1Nc1nc(Nc2cc(Cl)ccn2)ncc1Cl

Standard InChI:  InChI=1S/C16H13Cl2N5/c1-10-4-2-3-5-13(10)21-15-12(18)9-20-16(23-15)22-14-8-11(17)6-7-19-14/h2-9H,1H3,(H2,19,20,21,22,23)

Standard InChI Key:  LHPRBIBRVGNOET-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   32.8513  -25.9767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8502  -26.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5582  -27.2052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2679  -26.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2651  -25.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5564  -25.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9762  -27.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6833  -26.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3883  -27.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0949  -26.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0941  -25.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3807  -25.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6771  -25.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3884  -28.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9712  -25.5619    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.1421  -27.2043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4348  -26.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4399  -25.9781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7334  -25.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0244  -25.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0264  -26.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7335  -27.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3198  -27.2091    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  9 14  1  0
  5 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4644616

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 346.22

Molecular Weight (Monoisotopic): 345.0548

AlogP: 4.97

#Rotatable Bonds: 4

Polar Surface Area: 62.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.69

CX Basic pKa: 1.97

CX LogP: 5.30

CX LogD: 5.30

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -1.59

References

1. Wang Y, Chen X, Yan Y, Zhu X, Liu M, Liu X..  (2020)  Discovery and SARs of 5-Chloro-N4-phenyl-N2-(pyridin-2-yl)pyrimidine-2,4-diamine Derivatives as Oral Available and Dual CDK 6 and 9 Inhibitors with Potent Antitumor Activity.,  63  (6): [PMID:32129996] [10.1021/acs.jmedchem.9b02121]

Source

Source(1):

• Scientific Literature