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

ID: ALA4560849

PubChem CID: 155558190

Max Phase: Preclinical

Molecular Formula: C20H20BrFN4O2S

Molecular Weight: 479.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N1CCc2c(sc3ncnc(Nc4ccc(F)cc4Br)c23)C1

Standard InChI:  InChI=1S/C20H20BrFN4O2S/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(22)8-13(14)21/h4-5,8,10H,6-7,9H2,1-3H3,(H,23,24,25)

Standard InChI Key:  GUGASMLZENOCDQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   27.2218  -17.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2206  -18.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9287  -18.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6383  -18.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6355  -17.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9269  -17.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5126  -18.7187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5120  -19.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5107  -21.1688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2211  -20.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2186  -19.9413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8028  -20.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7997  -19.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0278  -21.0139    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.5456  -20.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0241  -19.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6958  -18.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8880  -18.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4098  -19.5283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7388  -20.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5926  -19.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1888  -18.8123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1792  -20.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3620  -20.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9487  -20.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9582  -19.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5412  -20.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3417  -17.0763    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.5140  -17.0827    0.0000 Br  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:

   

   ALA4560849

   ---

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: 479.38

Molecular Weight (Monoisotopic): 478.0474

AlogP: 5.63

#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: ┄

CX Basic pKa: 2.50

CX LogP: 5.25

CX LogD: 5.25

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -2.29

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