4-Methyl-N-(3-pyridin-2-yl-isoquinolin-1-yl)-benzamide

ID: ALA339261

Cas Number: 112575-49-2

PubChem CID: 10359831

Max Phase: Preclinical

Molecular Formula: C22H17N3O

Molecular Weight: 339.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)Nc2nc(-c3ccccn3)cc3ccccc23)cc1

Standard InChI:  InChI=1S/C22H17N3O/c1-15-9-11-16(12-10-15)22(26)25-21-18-7-3-2-6-17(18)14-20(24-21)19-8-4-5-13-23-19/h2-14H,1H3,(H,24,25,26)

Standard InChI Key:  XKGYBIWGVCSKAC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
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   -0.8708    0.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -0.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -1.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8708    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3958    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083    0.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -1.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    0.7583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333   -0.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4000   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -2.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4250   -0.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875    1.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3625    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    0.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750    1.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1500    1.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  1  1  0
  7  8  1  0
  8  6  1  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 14  2  0
 16 13  1  0
 17 15  1  0
 18  8  2  0
 19  6  2  0
 20 11  1  0
 21 10  1  0
 22 17  1  0
 23 25  2  0
 24 26  1  0
 25 19  1  0
 26 21  2  0
  5  7  2  0
 18 23  1  0
 16 17  2  0
 20 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA339261

   4-methyl-N-(3-(pyridin-2-yl)isoquinolin-1-yl)benzamide

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: 339.40

Molecular Weight (Monoisotopic): 339.1372

AlogP: 4.86

#Rotatable Bonds: 3

Polar Surface Area: 54.88

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.96

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: -1.11

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. 2. Structure affinity profile of a series of isoquinoline and quinazoline compounds.,  41  (21): [PMID:9767637] [10.1021/jm980037i]

2. de Zwart MA, van der Goot H, Timmerman H..  (1988)  Synthesis and copper-dependent antimycoplasmal activity of 1-amino-3-(2-pyridyl)isoquinoline derivatives. 1. Amides.,  31  (4): [PMID:3351847] [10.1021/jm00399a005]

3. Tafi A, Bernardini C, Botta M, Corelli F, Andreini M, Martinelli A, Ortore G, Baraldi PG, Fruttarolo F, Borea PA, Tuccinardi T..  (2006)  Pharmacophore based receptor modeling: the case of adenosine A3 receptor antagonists. An approach to the optimization of protein models.,  49  (14): [PMID:16821770] [10.1021/jm051112+]

Source

Source(1):

• Scientific Literature