4-(3-chlorophenyl)-8-fluoro-3-(4-fluorophenylsulfonyl)quinoline

ID: ALA4099425

PubChem CID: 25168656

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-c1cccc(Cl)c1

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

Standard InChI Key:  QFNIQTXZNSPEMV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    9.5663   -3.3263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9820   -4.0402    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.3952   -3.3225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -5.6963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8411   -5.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8425   -4.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1316   -4.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4152   -4.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159   -5.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1330   -5.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5506   -4.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5499   -3.2252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8390   -2.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8382   -1.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5485   -1.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2635   -1.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2642   -2.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2677   -4.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7069   -4.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7061   -5.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4204   -5.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1419   -5.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1301   -4.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4137   -4.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2663   -5.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1344   -6.5181    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8568   -5.6758    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.1258   -1.5750    0.0000 Cl  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
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  2 19  1  0
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  4 25  2  0
 10 26  1  0
 22 27  1  0
 14 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099425

   4-(3-Chlorophenyl)-8-fluoro-3-(4-fluorophenyl)sulfonylquinoline

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: -1.55

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