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

ID: ALA4645060

PubChem CID: 155665853

Max Phase: Preclinical

Molecular Formula: C21H24ClN7O

Molecular Weight: 425.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(Nc2nc(Nc3ccc(N4CCN(C)CC4)cn3)ncc2Cl)cc1

Standard InChI:  InChI=1S/C21H24ClN7O/c1-28-9-11-29(12-10-28)16-5-8-19(23-13-16)26-21-24-14-18(22)20(27-21)25-15-3-6-17(30-2)7-4-15/h3-8,13-14H,9-12H2,1-2H3,(H2,23,24,25,26,27)

Standard InChI Key:  JJKRSPZQJWOKSJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    6.5031  -26.0098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019  -26.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2100  -27.2383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9197  -26.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9168  -26.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2082  -25.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6280  -27.2363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6230  -25.5949    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7939  -27.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0865  -26.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0917  -26.0111    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3852  -25.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6762  -26.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6781  -26.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3853  -27.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682  -25.6019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9678  -24.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607  -26.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5528  -25.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599  -24.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524  -24.7855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444  -24.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3351  -26.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0401  -27.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7467  -26.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7458  -26.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0325  -25.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3288  -26.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4524  -25.5968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1613  -26.0033    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  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 26 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4645060

   ---

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: 425.92

Molecular Weight (Monoisotopic): 425.1731

AlogP: 3.77

#Rotatable Bonds: 6

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: 11.64

CX Basic pKa: 7.65

CX LogP: 3.98

CX LogD: 3.54

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.62

Np Likeness Score: -1.57

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