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

ID: ALA4100326

PubChem CID: 25167449

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)c1cnc2cc(F)ccc2c1-c1ccc(Cl)cc1

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

Standard InChI Key:  LDYYLSZINRPCHM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   44.3264   -2.8024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.7392   -3.5123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   45.1476   -2.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.3178   -5.1562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.6099   -4.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6135   -3.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9055   -3.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1939   -3.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1944   -4.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4827   -5.1576    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   41.9065   -5.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3169   -3.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3164   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6085   -2.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6079   -1.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3155   -1.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3274   -0.2459    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   44.0235   -1.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0239   -2.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0290   -3.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4564   -3.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4586   -4.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1661   -5.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.8838   -4.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.6078   -5.1405    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   46.8733   -3.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.1617   -3.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0253   -4.7495    0.0000 C   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
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 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
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 24 25  1  0
 26 24  1  0
 27 26  2  0
 21 27  1  0
 28 20  1  0
  4 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100326

   4-(4-Chlorophenyl)-7-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: 0.34

CX LogP: 5.62

CX LogD: 5.62

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -1.39

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