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

ID: ALA4638522

PubChem CID: 155665825

Max Phase: Preclinical

Molecular Formula: C20H21ClFN7

Molecular Weight: 413.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ccc(Nc3ncc(Cl)c(Nc4ccc(F)cc4)n3)nc2)CC1

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

Standard InChI Key:  WXGZTKYOSGMKGD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.6704   -5.9195    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0980   -5.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0980   -4.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3809   -4.3501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677   -4.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9486   -4.3519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357   -4.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5163   -4.3531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -4.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092   -5.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935   -6.0098    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3772   -5.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689   -6.0159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689   -6.8447    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849   -7.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935   -6.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513   -7.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245   -6.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2357   -5.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677   -5.5871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3809   -5.9995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3809   -6.8290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6639   -7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6639   -8.0649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9445   -8.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293   -8.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2293   -7.2332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9485   -6.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5158   -8.4745    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
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4638522

   ---

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: -1.88

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