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

ID: ALA4637018

PubChem CID: 155665810

Max Phase: Preclinical

Molecular Formula: C21H21ClF3N7O

Molecular Weight: 479.89

Molecule Type: Unknown

Names and Identifiers

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

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

Standard InChI Key:  FAMMAJJGTGZIMK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   33.9034  -14.3702    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.3321  -14.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3321  -13.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6192  -12.8043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9022  -13.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1875  -12.8061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4748  -13.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7597  -12.8073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0486  -13.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0486  -14.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3372  -14.4624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6212  -14.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9129  -14.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9129  -15.2944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3440  -15.6272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6287  -15.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3372  -15.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7637  -14.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4748  -14.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9022  -14.0414    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6192  -14.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6192  -15.2789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9025  -15.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9025  -16.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1835  -16.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1835  -17.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4609  -18.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4609  -18.8172    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.8920  -17.8267    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.8872  -18.4842    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.4685  -16.5081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4685  -15.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1874  -15.2744    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  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 25 31  2  0
 31 32  1  0
 32 33  2  0
 33 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4637018

   ---

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: -1.78

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