4-(4-Chlorophenyl)-3-((4-fluorophenyl)sulfonyl)quinoline-7-carbonitrile

ID: ALA4084830

PubChem CID: 53335885

Max Phase: Preclinical

Molecular Formula: C22H12ClFN2O2S

Molecular Weight: 422.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc2c(-c3ccc(Cl)cc3)c(S(=O)(=O)c3ccc(F)cc3)cnc2c1

Standard InChI:  InChI=1S/C22H12ClFN2O2S/c23-16-4-2-15(3-5-16)22-19-10-1-14(12-25)11-20(19)26-13-21(22)29(27,28)18-8-6-17(24)7-9-18/h1-11,13H

Standard InChI Key:  XJSYBGUWCVYNIB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   31.1152   -9.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5279  -10.1200    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.9363   -9.4076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1066  -11.7639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3986  -11.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4022  -10.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6943  -10.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9826  -10.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9831  -11.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2714  -11.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6952  -11.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1056  -10.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1052   -9.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3972   -8.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3967   -8.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1042   -7.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1161   -6.8536    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.8122   -8.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8127   -8.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8177  -10.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2451  -10.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2473  -11.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9549  -11.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6725  -11.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3965  -11.7482    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.6621  -10.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9504  -10.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8141  -11.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5637  -12.1739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  6  5  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11  5  2  0
 12  6  1  0
 12 13  1  0
 13 14  2  0
 15 14  1  0
 16 15  2  0
 16 17  1  0
 18 16  1  0
 19 18  2  0
 13 19  1  0
 20 12  2  0
 20  2  1  0
  2 21  1  0
 21 22  2  0
 23 22  1  0
 24 23  2  0
 24 25  1  0
 26 24  1  0
 27 26  2  0
 21 27  1  0
 28 20  1  0
  4 28  2  0
 10 29  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084830

   4-(4-Chlorophenyl)-3-(4-fluorophenyl)sulfonylquinoline-7-carbonitrile

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: 422.87

Molecular Weight (Monoisotopic): 422.0292

AlogP: 5.40

#Rotatable Bonds: 3

Polar Surface Area: 70.82

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.34

CX LogD: 5.34

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: -1.62

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