3-(3,5-difluorophenylsulfonyl)-7-fluoro-4-(3-methoxyphenyl)quinoline

ID: ALA4099016

PubChem CID: 25167717

Max Phase: Preclinical

Molecular Formula: C22H14F3NO3S

Molecular Weight: 429.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2c(S(=O)(=O)c3cc(F)cc(F)c3)cnc3cc(F)ccc23)c1

Standard InChI:  InChI=1S/C22H14F3NO3S/c1-29-17-4-2-3-13(7-17)22-19-6-5-14(23)11-20(19)26-12-21(22)30(27,28)18-9-15(24)8-16(25)10-18/h2-12H,1H3

Standard InChI Key:  IJSNUNHOXBEUSN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   18.4658  -12.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8816  -13.4578    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.2949  -12.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4515  -15.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7405  -14.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7419  -13.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0309  -13.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3144  -13.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3151  -14.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0323  -15.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4501  -13.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4493  -12.6429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7384  -12.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7376  -11.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4479  -10.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1630  -11.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1636  -12.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1673  -13.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6065  -13.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6058  -14.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3202  -15.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0417  -14.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0300  -13.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3135  -13.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1659  -14.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7365  -13.4403    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.3194  -15.9290    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.6034  -15.1101    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.0251  -10.9925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0235  -10.1708    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
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 11 12  1  0
 12 13  2  0
 14 13  1  0
 15 14  2  0
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 12 17  1  0
 18 11  2  0
 18  2  1  0
  2 19  1  0
 19 20  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
 25 18  1  0
  4 25  2  0
 23 26  1  0
 21 27  1  0
  9 28  1  0
 14 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099016

   3-(3,5-Difluorophenyl)sulfonyl-7-fluoro-4-(3-methoxyphenyl)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: 429.42

Molecular Weight (Monoisotopic): 429.0646

AlogP: 5.16

#Rotatable Bonds: 4

Polar Surface Area: 56.26

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.26

CX LogP: 5.00

CX LogD: 5.00

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: -1.16

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