4-(Piperazin-1-yl)-2-(pyridin-4-yl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-b]pyridine

ID: ALA4649467

PubChem CID: 156022110

Max Phase: Preclinical

Molecular Formula: C20H22N4S

Molecular Weight: 350.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  c1cc(-c2cc(N3CCNCC3)c3c4c(sc3n2)CCCC4)ccn1

Standard InChI:  InChI=1S/C20H22N4S/c1-2-4-18-15(3-1)19-17(24-11-9-22-10-12-24)13-16(23-20(19)25-18)14-5-7-21-8-6-14/h5-8,13,22H,1-4,9-12H2

Standard InChI Key:  CAXRWBVAXDTUMZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
    5.5426   -6.4948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2523   -6.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2494   -5.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -4.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8346   -6.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8358   -5.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0576   -6.3369    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.5786   -5.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -5.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357   -4.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9217   -4.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4366   -4.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7655   -5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5370   -4.0403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9571   -6.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9570   -7.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6646   -7.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3726   -7.3080    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3687   -6.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6606   -6.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2463   -3.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445   -2.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5367   -2.4090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8291   -2.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -3.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  9  1  0
  8  7  1  0
  7  5  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  4 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  2 15  1  0
 14 21  1  0
 14 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4649467

   ---

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: 350.49

Molecular Weight (Monoisotopic): 350.1565

AlogP: 3.65

#Rotatable Bonds: 2

Polar Surface Area: 41.05

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.82

CX LogP: 3.97

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -1.68

References

1. Liu X, Wilson MW, Liu K, Lee P, Yeomans L, Hagen SE, Lin CM, Wen B, Sun D, White AD, Showalter HD, Antonetti DA..  (2020)  Synthesis and structure-activity relationships of thieno[2,3-d]pyrimidines as atypical protein kinase C inhibitors to control retinal vascular permeability and cytokine-induced edema.,  28  (11): [PMID:32327351] [10.1016/j.bmc.2020.115480]

Source

Source(1):

• Scientific Literature