N-Cyclopentyl-4-methyl-5-(2-((5-(piperazin-1-yl)pyridin-2-yl)-amino)pyrimidin-4-yl)thiazol-2-amine

ID: ALA4071812

PubChem CID: 126534285

Max Phase: Preclinical

Molecular Formula: C22H28N8S

Molecular Weight: 436.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(NC2CCCC2)sc1-c1ccnc(Nc2ccc(N3CCNCC3)cn2)n1

Standard InChI:  InChI=1S/C22H28N8S/c1-15-20(31-22(26-15)27-16-4-2-3-5-16)18-8-9-24-21(28-18)29-19-7-6-17(14-25-19)30-12-10-23-11-13-30/h6-9,14,16,23H,2-5,10-13H2,1H3,(H,26,27)(H,24,25,28,29)

Standard InChI Key:  JTZWTKLEXMYEMU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    2.5465   -3.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7192   -2.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4733   -2.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3881   -1.7992    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814   -1.6266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468   -0.8724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -0.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745   -0.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1773   -0.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331   -1.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9029   -1.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679   -2.3405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1872   -3.0332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9022   -2.6216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6163   -3.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3313   -2.6235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0452   -3.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7603   -2.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4742   -3.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4731   -3.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1871   -4.2773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9021   -3.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6161   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6149   -5.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8999   -5.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1860   -5.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7580   -4.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0441   -3.8620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6152   -3.8601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001   -4.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1862   -3.8582    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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  7 11  1  0
  5 12  2  0
  2 12  1  0
  3 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 21 26  1  0
 20 27  1  0
 27 28  2  0
 17 28  1  0
 15 29  2  0
 29 30  1  0
 30 31  2  0
 13 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4071812

   ---

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: 436.59

Molecular Weight (Monoisotopic): 436.2158

AlogP: 3.81

#Rotatable Bonds: 6

Polar Surface Area: 90.89

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.35

CX Basic pKa: 8.86

CX LogP: 3.45

CX LogD: 1.98

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: -1.63

References

1. Tadesse S, Yu M, Mekonnen LB, Lam F, Islam S, Tomusange K, Rahaman MH, Noll B, Basnet SK, Teo T, Albrecht H, Milne R, Wang S..  (2017)  Highly Potent, Selective, and Orally Bioavailable 4-Thiazol-N-(pyridin-2-yl)pyrimidin-2-amine Cyclin-Dependent Kinases 4 and 6 Inhibitors as Anticancer Drug Candidates: Design, Synthesis, and Evaluation.,  60  (5): [PMID:28156111] [10.1021/acs.jmedchem.6b01670]

Source

Source(1):

• Scientific Literature