7-Chloro-4-(4-chlorophenyl)-6-fluoro-3-((4-fluorophenyl)-sulfonyl)quinoline

ID: ALA4102752

PubChem CID: 137657953

Max Phase: Preclinical

Molecular Formula: C21H11Cl2F2NO2S

Molecular Weight: 450.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1ccc(F)cc1)c1cnc2cc(Cl)c(F)cc2c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H11Cl2F2NO2S/c22-13-3-1-12(2-4-13)21-16-9-18(25)17(23)10-19(16)26-11-20(21)29(27,28)15-7-5-14(24)6-8-15/h1-11H

Standard InChI Key:  HRZDDKSTWRLIST-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   13.3021   -3.7599    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.7105   -3.0475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8807   -5.4038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1728   -4.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1764   -4.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4684   -3.7685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7568   -4.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0447   -3.7629    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7573   -4.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0456   -5.4052    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4694   -5.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8798   -3.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8793   -2.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1714   -2.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1708   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8784   -1.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8903   -0.4935    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.5864   -1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5868   -2.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5919   -4.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0193   -4.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0215   -4.9861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7290   -5.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4467   -4.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1707   -5.3881    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.4362   -4.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7246   -3.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5882   -4.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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  4  5  1  0
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  2 22  1  0
 22 23  2  0
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 22 28  1  0
 29 21  1  0
  4 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102752

   ---

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: 450.29

Molecular Weight (Monoisotopic): 448.9856

AlogP: 6.32

#Rotatable Bonds: 3

Polar Surface Area: 47.03

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.23

CX LogD: 6.23

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -1.57

References

1. Galambos J, Bielik A, Krasavin M, Orgován Z, Domány G, Nógrádi K, Wágner G, Balogh GT, Béni Z, Kóti J, Szakács Z, Bobok A, Kolok S, Mikó-Bakk ML, Vastag M, Sághy K, Laszy J, Halász AS, Balázs O, Gál K, Greiner I, Szombathelyi Z, Keserű GM..  (2017)  Discovery and Preclinical Characterization of 3-((4-(4-Chlorophenyl)-7-fluoroquinoline-3-yl)sulfonyl)benzonitrile, a Novel Non-acetylenic Metabotropic Glutamate Receptor 5 (mGluR5) Negative Allosteric Modulator for Psychiatric Indications.,  60  (6): [PMID:28212015] [10.1021/acs.jmedchem.6b01858]

Source

Source(1):

• Scientific Literature