5-chloro-N4-(3-fluorophenyl)-N2-[5-(4-methylpiperazin-1-yl)-2-pyridyl]pyrimidine-2,4-diamine

ID: ALA4648605

PubChem CID: 155665836

Max Phase: Preclinical

Molecular Formula: C20H21ClFN7

Molecular Weight: 413.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ccc(Nc3ncc(Cl)c(Nc4cccc(F)c4)n3)nc2)CC1

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

Standard InChI Key:  GDVOZEDGMULABW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.4558  -13.9363    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8835  -13.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8835  -12.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1661  -12.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4529  -12.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7338  -12.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0207  -12.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3053  -12.3697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940  -12.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5940  -13.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781  -14.0267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1617  -13.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4533  -14.0369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4533  -14.8617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1695  -15.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781  -14.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7356  -15.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3093  -14.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0207  -13.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4529  -13.6040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1661  -14.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1661  -14.8418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4490  -15.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4490  -16.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7297  -16.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0143  -16.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0143  -15.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337  -14.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7297  -17.3203    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
 15 16  1  0
 16 11  1  0
 14 17  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
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4648605

   ---

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: 11.64

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