5-Chloro-N4-(3-methoxybenzyl)-N2-(5-(4-methylpiperazin-1-yl)pyridin-2-yl)pyrimidine-2,4-diamine

ID: ALA4645755

PubChem CID: 155665856

Max Phase: Preclinical

Molecular Formula: C22H26ClN7O

Molecular Weight: 439.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(CNc2nc(Nc3ccc(N4CCN(C)CC4)cn3)ncc2Cl)c1

Standard InChI:  InChI=1S/C22H26ClN7O/c1-29-8-10-30(11-9-29)17-6-7-20(24-14-17)27-22-26-15-19(23)21(28-22)25-13-16-4-3-5-18(12-16)31-2/h3-7,12,14-15H,8-11,13H2,1-2H3,(H2,24,25,26,27,28)

Standard InChI Key:  CGAOUCZITPFFDG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    6.6682  -18.7912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6670  -19.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3751  -20.0197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0847  -19.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0819  -18.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3733  -18.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7931  -20.0178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7881  -18.3764    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9590  -20.0188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2516  -19.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568  -18.7926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5503  -18.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412  -18.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8432  -19.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5504  -20.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1333  -18.3834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1329  -17.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258  -18.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7179  -18.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4250  -17.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175  -17.5669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095  -17.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5002  -19.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2085  -20.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2052  -20.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9127  -21.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6207  -20.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6168  -20.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9087  -19.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3224  -19.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0322  -20.0002    0.0000 C   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
  5  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 17 20  1  0
 19 21  1  0
 21 20  1  0
 21 22  1  0
  7 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 28 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4645755

   ---

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: 439.95

Molecular Weight (Monoisotopic): 439.1887

AlogP: 3.64

#Rotatable Bonds: 7

Polar Surface Area: 78.44

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.69

CX Basic pKa: 7.65

CX LogP: 3.74

CX LogD: 3.30

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -1.61

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