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

ID: ALA4645617

PubChem CID: 155665837

Max Phase: Preclinical

Molecular Formula: C21H21ClF3N7O

Molecular Weight: 479.89

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H21ClF3N7O/c1-31-8-10-32(11-9-31)15-4-7-18(26-12-15)29-20-27-13-17(22)19(30-20)28-14-2-5-16(6-3-14)33-21(23,24)25/h2-7,12-13H,8-11H2,1H3,(H2,26,27,28,29,30)

Standard InChI Key:  GVNBXUWQTFPDDE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   34.8258   -6.1289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.2548   -5.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2548   -4.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5423   -4.5639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8296   -4.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1111   -4.5655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3987   -4.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6840   -4.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9732   -4.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9732   -5.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2621   -6.2212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5464   -5.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8383   -6.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8383   -7.0528    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2698   -7.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5539   -7.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2621   -7.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6920   -6.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3987   -5.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8296   -5.8003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.5423   -6.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5423   -7.0374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8259   -7.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8259   -8.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1071   -8.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3924   -8.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6801   -8.6756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9656   -8.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3921   -8.5840    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.9656   -7.5984    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.3971   -7.9268    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.3924   -7.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1151   -7.0329    0.0000 C   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
 26 32  1  0
 32 33  2  0
 33 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4645617

   ---

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: 479.89

Molecular Weight (Monoisotopic): 479.1448

AlogP: 4.66

#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: 5.57

CX LogD: 5.13

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.53

Np Likeness Score: -1.67

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