4-(5-Chloro-6-fluoroindole-3-yl)-6,7-dimethoxyquinazoline

ID: ALA515401

PubChem CID: 24863865

Max Phase: Preclinical

Molecular Formula: C18H13ClFN3O2

Molecular Weight: 357.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ncnc(-c3c[nH]c4cc(F)c(Cl)cc34)c2cc1OC

Standard InChI:  InChI=1S/C18H13ClFN3O2/c1-24-16-4-10-15(6-17(16)25-2)22-8-23-18(10)11-7-21-14-5-13(20)12(19)3-9(11)14/h3-8,21H,1-2H3

Standard InChI Key:  CKNICHHQTFEWGN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    4.2011    2.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1999    1.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9151    1.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9133    3.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291    2.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6299    1.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3456    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0610    1.7691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0562    2.5996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3399    3.0071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3494    0.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8703   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3617   -0.8050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1368    0.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1433   -0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8568   -0.9419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5642   -0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5536    0.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8396    0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2630    0.7217    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4860    3.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7712    2.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4846    1.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7701    1.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2835   -0.9297    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 12 13  1  0
 13 15  1  0
 14 11  1  0
  7 11  1  0
  3  6  2  0
  6  7  1  0
 14 15  2  0
  1  2  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  5  4  2  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19 14  1  0
  4  1  1  0
 18 20  1  0
  9 10  2  0
  1 21  1  0
 10  5  1  0
 21 22  1  0
 11 12  2  0
  2 23  1  0
 23 24  1  0
  2  3  1  0
 17 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA515401

   4-(5-Chloro-6-fluoroindole-3-yl)-6,7-dimethoxyquinazoline

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: 357.77

Molecular Weight (Monoisotopic): 357.0680

AlogP: 4.59

#Rotatable Bonds: 3

Polar Surface Area: 60.03

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.39

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -0.78

References

1. Lüth A, Löwe W..  (2008)  Syntheses of 4-(indole-3-yl)quinazolines: a new class of epidermal growth factor receptor tyrosine kinase inhibitors.,  43  (7): [PMID:17981366] [10.1016/j.ejmech.2007.09.018]

Source

Source(1):

• Scientific Literature