2-(3-((dimethylamino)methyl)phenyl)-4-(4-methyl-1H-indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitrile

ID: ALA402818

PubChem CID: 25066843

Max Phase: Preclinical

Molecular Formula: C26H23N5S

Molecular Weight: 437.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(Nc2c(C#N)cnc3sc(-c4cccc(CN(C)C)c4)cc23)ccc2[nH]ccc12

Standard InChI:  InChI=1S/C26H23N5S/c1-16-20-9-10-28-23(20)8-7-22(16)30-25-19(13-27)14-29-26-21(25)12-24(32-26)18-6-4-5-17(11-18)15-31(2)3/h4-12,14,28H,15H2,1-3H3,(H,29,30)

Standard InChI Key:  CSCOHEYTBLBQMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   11.7250    2.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7238    1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4383    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1543    1.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4365    2.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1526    2.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7679    3.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4320    3.7602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6092    3.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0108    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0094    1.2142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0088    0.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0076   -1.2579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7243   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7218   -0.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4347    0.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1465    0.8120    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2933   -0.8442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2947   -0.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5079    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0200   -0.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5055   -1.0986    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1980   -0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875    0.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9638    0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5494   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9649   -1.1402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7873   -1.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5530    1.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9669    1.7189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5562    2.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7914    1.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 12  1  0
  4  6  1  0
 15 16  1  0
  6  7  1  0
 16 17  3  0
 18 19  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  5  1  1  0
  1 10  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
  5  6  2  0
  2 11  1  0
 23 24  2  0
 24 25  1  0
 11 12  1  0
 25 26  2  0
 12 19  2  0
 26 27  1  0
  2  3  1  0
 27 28  2  0
 28 23  1  0
 21 23  1  0
 18 13  2  0
 25 29  1  0
  1  2  2  0
 29 30  1  0
 13 14  1  0
 30 31  1  0
  3  4  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA402818

   2-(3-((dimethylamino)methyl)phenyl)-4-(4-methyl-1H-indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitrile

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: 437.57

Molecular Weight (Monoisotopic): 437.1674

AlogP: 6.43

#Rotatable Bonds: 5

Polar Surface Area: 67.74

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.96

CX LogP: 5.49

CX LogD: 3.93

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: -1.57

References

1. Boschelli DH, Wu B, Barrios Sosa AC, Chen J, Asselin M, Cole DC, Lee J, Yang X, Chaudhary D..  (2008)  Synthesis and PKCtheta inhibitory activity of a series of 4-(indol-5-ylamino)thieno[2,3-b]pyridine-5-carbonitriles.,  18  (9): [PMID:18434148] [10.1016/j.bmcl.2008.03.077]

2. Wu B, Boschelli DH, Lee J, Yang X, Chaudhary D..  (2009)  Second generation 4-(4-methyl-1H-indol-5-ylamino)-2-phenylthieno[2,3-b]pyridine-5-carbonitrile PKCtheta inhibitors.,  19  (3): [PMID:19111463] [10.1016/j.bmcl.2008.12.021]

Source

Source(1):

• Scientific Literature