4-Chloro-N-(3-pyridin-2-yl-isoquinolin-1-yl)-benzamidine

ID: ALA339097

PubChem CID: 44352279

Max Phase: Preclinical

Molecular Formula: C21H15ClN4

Molecular Weight: 358.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(Nc1nc(-c2ccccn2)cc2ccccc12)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H15ClN4/c22-16-10-8-14(9-11-16)20(23)26-21-17-6-2-1-5-15(17)13-19(25-21)18-7-3-4-12-24-18/h1-13H,(H2,23,25,26)

Standard InChI Key:  IULSXRJQCDYYRM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    6.0667   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -5.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -4.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -3.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -6.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -3.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3667   -5.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042   -7.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3417   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -8.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3417   -7.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -7.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6167   -9.1417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -3.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2167   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7  8  1  0
  8  6  2  0
  9  4  1  0
 10  5  1  0
 11 10  2  0
 12  4  2  0
 13  9  2  0
 14  9  1  0
 15 16  1  0
 16 14  2  0
 17 13  1  0
 18 15  1  0
 19  8  1  0
 20  6  1  0
 21 11  1  0
 22 10  1  0
 23 25  1  0
 24 26  1  0
 25 20  2  0
 26 22  2  0
  5  7  2  0
 23 19  2  0
 17 15  2  0
 21 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA339097

   4-Chloro-N-(3-pyridin-2-yl-isoquinolin-1-yl)-benzamidine

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: 358.83

Molecular Weight (Monoisotopic): 358.0985

AlogP: 5.39

#Rotatable Bonds: 3

Polar Surface Area: 61.66

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.83

CX LogP: 5.25

CX LogD: 5.24

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: -0.87

References

1. van Muijlwijk-Koezen JE, Timmerman H, Link R, van der Goot H, IJzerman AP..  (1998)  A novel class of adenosine A3 receptor ligands. 1. 3-(2-Pyridinyl)isoquinoline derivatives.,  41  (21): [PMID:9767636] [10.1021/jm980036q]

2. de Zwart MA, van der Goot H, Timmerman H..  (1989)  Synthesis and copper-dependent antimycoplasmal activity of 1-amino-3-(2-pyridyl)isoquinoline derivatives. 2. Amidines.,  32  (2): [PMID:2913309] [10.1021/jm00122a033]

Source

Source(1):

• Scientific Literature