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

ID: ALA4101273

PubChem CID: 57577152

Max Phase: Preclinical

Molecular Formula: C21H12Cl2FNO2S

Molecular Weight: 432.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1ccc(F)cc1)c1cnc2ccc(Cl)cc2c1-c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C21H12Cl2FNO2S/c22-14-3-1-13(2-4-14)21-18-11-15(23)5-10-19(18)25-12-20(21)28(26,27)17-8-6-16(24)7-9-17/h1-12H

Standard InChI Key:  KKSHKWLTQLJETO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    4.3336  -10.3057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7463  -11.0156    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547  -10.3032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3250  -12.6595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170  -12.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206  -11.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9127  -11.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010  -11.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4889  -11.0185    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2015  -12.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136  -12.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240  -11.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3236  -10.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6156   -9.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   -8.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3227   -8.5641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3345   -7.7492    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0306   -8.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0311   -9.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0361  -11.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4635  -11.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4657  -12.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1733  -12.6521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8909  -12.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6150  -12.6438    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8805  -11.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1688  -11.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0325  -12.2528    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  1  0
  8 10  2  0
 10 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
M  END

Alternative Forms

1. Parent:

   

   ALA4101273

   6-Chloro-4-(4-chlorophenyl)-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: 432.30

Molecular Weight (Monoisotopic): 430.9950

AlogP: 6.18

#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: 6.08

CX LogD: 6.08

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -1.43

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