4-(4-Chlorophenyl)-8-fluoro-3-((4-fluorophenyl)sulfonyl)quinoline

ID: ALA4092590

PubChem CID: 25168657

Max Phase: Preclinical

Molecular Formula: C21H12ClF2NO2S

Molecular Weight: 415.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1ccc(F)cc1)c1cnc2c(F)cccc2c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H12ClF2NO2S/c22-14-6-4-13(5-7-14)20-17-2-1-3-18(24)21(17)25-12-19(20)28(26,27)16-10-8-15(23)9-11-16/h1-12H

Standard InChI Key:  ZKWGJICQXOQLFW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   28.0652   -2.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4779   -3.5040    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.8863   -2.7916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0566   -5.1479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3486   -4.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3522   -3.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6442   -3.5126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9326   -3.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9331   -4.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6452   -5.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0556   -3.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0552   -2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3472   -2.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3467   -1.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0542   -1.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0661   -0.2376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.7622   -1.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7626   -2.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7677   -3.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1951   -3.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1973   -4.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9048   -5.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6225   -4.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3465   -5.1322    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.6120   -3.9051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9004   -3.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7640   -4.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6468   -5.9679    0.0000 F   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
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 12 13  2  0
 14 13  1  0
 15 14  2  0
 15 16  1  0
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 12 18  1  0
 19 11  2  0
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  2 20  1  0
 20 21  2  0
 22 21  1  0
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 26 25  2  0
 20 26  1  0
 27 19  1  0
  4 27  2  0
 10 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092590

   4-(4-Chlorophenyl)-8-fluoro-3-[(4-fluorophenyl)sulfonyl]quinoline

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: 415.85

Molecular Weight (Monoisotopic): 415.0245

AlogP: 5.67

#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: 5.62

CX LogD: 5.62

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.50

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