N-(4-bromophenyl)-3-cyano-2-(1-methyl-1H-pyrazole-4-carboxamido)-4,7-dihydrothieno[2,3-c]pyridine-6(5H)-carboxamide

ID: ALA5201403

PubChem CID: 168291088

Max Phase: Preclinical

Molecular Formula: C20H17BrN6O2S

Molecular Weight: 485.37

Names and Identifiers

Canonical SMILES:  Cn1cc(C(=O)Nc2sc3c(c2C#N)CCN(C(=O)Nc2ccc(Br)cc2)C3)cn1

Standard InChI:  InChI=1S/C20H17BrN6O2S/c1-26-10-12(9-23-26)18(28)25-19-16(8-22)15-6-7-27(11-17(15)30-19)20(29)24-14-4-2-13(21)3-5-14/h2-5,9-10H,6-7,11H2,1H3,(H,24,29)(H,25,28)

Standard InChI Key:  WOWCHARCBNEZJP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -1.2062   -0.5115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2166   -0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    0.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4968    0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958    0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776   -0.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9957   -0.7652    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027   -0.0986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7172   -0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5423   -0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0267   -1.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107   -1.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8107   -0.3998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0267   -0.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3026   -1.5286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094    1.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4230    2.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9187   -0.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9184   -1.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4769    0.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6317   -0.5122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3443   -0.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0528   -0.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7648   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7649   -1.7460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0469   -2.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3378   -1.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4769   -2.1588    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
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 29 24  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5201403

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 485.37

Molecular Weight (Monoisotopic): 484.0317

AlogP: 3.96

#Rotatable Bonds: 3

Polar Surface Area: 103.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.80

CX Basic pKa: 1.16

CX LogP: 3.31

CX LogD: 3.31

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.59

Np Likeness Score: -2.77

References

1. Jin W, Zhang T, Zhou W, He P, Sun Y, Hu S, Chen H, Ma X, Peng Y, Yi Z, Liu M, Chen Y..  (2022)  Discovery of 2-Amino-3-cyanothiophene Derivatives as Potent STAT3 Inhibitors for the Treatment of Osteosarcoma Growth and Metastasis.,  65  (9.0): [PMID:35476936] [10.1021/acs.jmedchem.2c00004]

Source

Source(1):

• Scientific Literature