Tert-butyl 4-((2,4-difluorophenyl)amino)-5,8-dihydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(6H)-carboxylate

ID: ALA4560334

PubChem CID: 155558154

Max Phase: Preclinical

Molecular Formula: C20H20F2N4O2S

Molecular Weight: 418.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N1CCc2c(sc3ncnc(Nc4ccc(F)cc4F)c23)C1

Standard InChI:  InChI=1S/C20H20F2N4O2S/c1-20(2,3)28-19(27)26-7-6-12-15(9-26)29-18-16(12)17(23-10-24-18)25-14-5-4-11(21)8-13(14)22/h4-5,8,10H,6-7,9H2,1-3H3,(H,23,24,25)

Standard InChI Key:  CPKVWABPQNYDQL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   17.2834  -17.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2823  -18.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9903  -18.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7000  -18.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6971  -17.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9885  -17.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5742  -18.7848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5736  -19.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5724  -21.2348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2828  -20.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2803  -20.0073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8645  -20.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8614  -20.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0894  -21.0799    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.6072  -20.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0857  -19.7642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7575  -19.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9497  -18.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4714  -19.5943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8004  -20.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6542  -19.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2504  -18.8784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2408  -20.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4237  -20.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0103  -20.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0199  -19.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6029  -20.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4033  -17.1423    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.5756  -17.1488    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  1  0
  8 13  2  0
 12  9  2  0
  9 10  1  0
 10 11  2  0
 11  8  1  0
 12 13  1  0
 13 16  1  0
 15 14  1  0
 14 12  1  0
 15 16  2  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  5 28  1  0
  1 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560334

   ---

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: 418.47

Molecular Weight (Monoisotopic): 418.1275

AlogP: 5.01

#Rotatable Bonds: 2

Polar Surface Area: 67.35

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.64

CX Basic pKa: 2.45

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -2.34

References

1. Zhang M, Jiang L, Tao J, Pan Z, He M, Su D, He G, Jiang Q..  (2019)  Design, synthesis and biological evaluation of 4-aniline-thieno[2,3-d]pyrimidine derivatives as MNK1 inhibitors against renal cell carcinoma and nasopharyngeal carcinoma.,  27  (11): [PMID:31014565] [10.1016/j.bmc.2019.04.022]

Source

Source(1):

• Scientific Literature