2-(3-Bromophenyl)carbonylamino-3-cyano-6-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene

ID: ALA5199357

PubChem CID: 3591044

Max Phase: Preclinical

Molecular Formula: C17H15BrN2OS

Molecular Weight: 375.29

Names and Identifiers

Canonical SMILES:  CC1CCc2c(sc(NC(=O)c3cccc(Br)c3)c2C#N)C1

Standard InChI:  InChI=1S/C17H15BrN2OS/c1-10-5-6-13-14(9-19)17(22-15(13)7-10)20-16(21)11-3-2-4-12(18)8-11/h2-4,8,10H,5-7H2,1H3,(H,20,21)

Standard InChI Key:  IYGFYQAAUZVGPL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -2.8418    0.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8418   -0.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -1.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298    0.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4177    0.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178   -0.8106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365   -1.0645    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1535   -0.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6365    0.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812    1.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    1.8316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -0.3998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0839   -1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9090   -1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714   -1.8288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -1.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1432   -1.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565   -1.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1396   -0.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -0.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5496    0.3162    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5565   -1.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  5  4  1  0
  3  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  9 10  1  0
 10 11  3  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 19 21  1  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5199357

   3-bromo-N-(3-cyano-6-methyl-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)benzamide

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: 375.29

Molecular Weight (Monoisotopic): 374.0088

AlogP: 4.76

#Rotatable Bonds: 2

Polar Surface Area: 52.89

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.63

CX Basic pKa: ┄

CX LogP: 5.51

CX LogD: 5.51

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -2.15

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