5-Chloro-N4-(2-(isopropylsulfonyl)phenyl)-N2-(2-methoxy-4-(4-(piperidin-1-ylmethyl)thiazol-2-yl)phenyl)pyrimidine-2,4-diamine

ID: ALA4160984

PubChem CID: 145956712

Max Phase: Preclinical

Molecular Formula: C29H33ClN6O3S2

Molecular Weight: 613.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-c2nc(CN3CCCCC3)cs2)ccc1Nc1ncc(Cl)c(Nc2ccccc2S(=O)(=O)C(C)C)n1

Standard InChI:  InChI=1S/C29H33ClN6O3S2/c1-19(2)41(37,38)26-10-6-5-9-24(26)33-27-22(30)16-31-29(35-27)34-23-12-11-20(15-25(23)39-3)28-32-21(18-40-28)17-36-13-7-4-8-14-36/h5-6,9-12,15-16,18-19H,4,7-8,13-14,17H2,1-3H3,(H2,31,33,34,35)

Standard InChI Key:  SQAJZADVUTUJJT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 45  0  0  0  0  0  0  0  0999 V2000
    9.2698   -3.9745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8653   -4.6844    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6823   -4.6797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4075   -8.3490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5873   -8.3442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7605   -6.3896    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.0812   -6.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3083   -7.6372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1280   -7.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4075   -6.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3096   -6.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2881   -5.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5674   -5.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8681   -5.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8895   -6.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6103   -6.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5459   -4.5388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8251   -4.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1473   -5.3959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4480   -5.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7272   -5.4331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0279   -5.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0494   -6.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7702   -7.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4695   -6.6443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3071   -5.4703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6078   -5.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8871   -5.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1878   -5.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2092   -6.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9300   -7.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6293   -6.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1691   -4.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4481   -4.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1911   -3.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3501   -7.1101    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.8101   -9.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6267   -9.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0447   -8.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6400   -7.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8173   -7.6377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  6 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  1  0
 13 17  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 27 32  2  0
 33 34  1  0
 33 35  1  0
  2 33  1  0
 28  2  1  0
 26 27  1  0
 22 26  1  0
 23 36  1  0
 19 20  1  0
 14 19  1  0
  7 11  1  0
  5  9  1  0
  4  5  1  0
  4 37  1  0
  4 41  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4160984

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 613.21

Molecular Weight (Monoisotopic): 612.1744

AlogP: 6.92

#Rotatable Bonds: 10

Polar Surface Area: 109.34

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.46

CX Basic pKa: 7.41

CX LogP: 6.12

CX LogD: 5.82

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.20

Np Likeness Score: -1.91

References

1. Wang Y, Chen S, Hu G, Wang J, Gou W, Zuo D, Gu Y, Gong P, Zhai X..  (2018)  Discovery of novel 2,4-diarylaminopyrimidine analogues as ALK and ROS1 dual inhibitors to overcome crizotinib-resistant mutants including G1202R.,  143  [PMID:29174809] [10.1016/j.ejmech.2017.11.008]

Source

Source(1):

• Scientific Literature