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

ID: ALA4643366

PubChem CID: 155665860

Max Phase: Preclinical

Molecular Formula: C21H20ClF4N7

Molecular Weight: 481.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1CCN(c2ccc(Nc3ncc(Cl)c(Nc4ccc(F)c(C(F)(F)F)c4)n3)nc2)CC1

Standard InChI:  InChI=1S/C21H20ClF4N7/c1-32-6-8-33(9-7-32)14-3-5-18(27-11-14)30-20-28-12-16(22)19(31-20)29-13-2-4-17(23)15(10-13)21(24,25)26/h2-5,10-12H,6-9H2,1H3,(H2,27,28,29,30,31)

Standard InChI Key:  BWRICAUVTXMEPX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.1549  -11.3965    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5842  -11.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5842  -10.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718   -9.8320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1554  -10.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -9.8298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423   -9.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255   -8.5938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7255   -7.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407   -7.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4407   -6.5354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242   -6.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242   -5.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421   -4.8888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421   -4.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1540   -5.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1540   -6.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -7.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -8.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1554  -11.0640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718  -11.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718  -12.3004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1557  -12.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1557  -13.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4374  -13.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230  -13.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230  -12.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160  -12.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4434  -12.6222    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.0160  -11.6359    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4471  -11.9613    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4413  -12.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0103  -13.9433    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  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 27 32  2  0
 32 23  1  0
 26 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4643366

   ---

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: 481.89

Molecular Weight (Monoisotopic): 481.1405

AlogP: 4.92

#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: 5.16

CX LogD: 4.72

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.50

Np Likeness Score: -1.95

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