5-chloro-N4-(2-fluorophenyl)-N2-[5-(4-methylpiperazin-1-yl)-2-pyridyl]pyrimidine-2,4-diamine

ID: ALA4646735

PubChem CID: 155665813

Max Phase: Preclinical

Molecular Formula: C20H21ClFN7

Molecular Weight: 413.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ccc(Nc3ncc(Cl)c(Nc4ccccc4F)n3)nc2)CC1

Standard InChI:  InChI=1S/C20H21ClFN7/c1-28-8-10-29(11-9-28)14-6-7-18(23-12-14)26-20-24-13-15(21)19(27-20)25-17-5-3-2-4-16(17)22/h2-7,12-13H,8-11H2,1H3,(H2,23,24,25,26,27)

Standard InChI Key:  JDYJRRCAXPQDJY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   22.1677   -5.3668    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.5969   -5.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5969   -4.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8824   -3.8002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1679   -4.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4557   -3.8019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7414   -4.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0249   -3.8072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3164   -4.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3164   -5.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6034   -5.4604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8899   -5.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1802   -5.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1802   -6.2914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6117   -6.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8976   -6.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6034   -6.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0329   -5.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7414   -5.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1679   -5.0376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8824   -5.4502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8824   -6.2758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1682   -6.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1682   -7.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4476   -7.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7351   -7.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7351   -6.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4557   -6.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8789   -7.9207    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 11  1  0
 10 18  1  0
 18 19  2  0
 19  7  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 21 22  1  0
 22 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
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4646735

   ---

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: 413.89

Molecular Weight (Monoisotopic): 413.1531

AlogP: 3.90

#Rotatable Bonds: 5

Polar Surface Area: 69.21

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.61

CX Basic pKa: 7.65

CX LogP: 4.28

CX LogD: 3.84

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.97

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