N-[4-(2-Fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzenesulfonamide

ID: ALA140071

PubChem CID: 10457047

Max Phase: Preclinical

Molecular Formula: C18H14F4N2O4S2

Molecular Weight: 462.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)Nc2nc(-c3cc(C(F)(F)F)ccc3F)cs2)cc1OC

Standard InChI:  InChI=1S/C18H14F4N2O4S2/c1-27-15-6-4-11(8-16(15)28-2)30(25,26)24-17-23-14(9-29-17)12-7-10(18(20,21)22)3-5-13(12)19/h3-9H,1-2H3,(H,23,24)

Standard InChI Key:  HEONEOMFRWFNEL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    4.4792   -2.5167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -2.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -2.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -2.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -1.9167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -2.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -2.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -3.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -1.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5167   -2.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500   -3.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667   -3.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -1.9292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -2.8292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -2.2292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -3.7292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -4.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -3.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -4.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  1  0
  7 12  1  0
  8  1  1  0
  9  3  1  0
 10  6  2  0
 11  9  1  0
 12 10  1  0
 13  8  2  0
 14  1  2  0
 15  1  2  0
 16 13  1  0
 17  6  1  0
 18 25  1  0
 19  8  1  0
 20 21  1  0
 21 17  2  0
 22  7  1  0
 23  7  1  0
 24  7  1  0
 25 19  2  0
 26 17  1  0
 27 16  1  0
 28 18  1  0
 29 27  1  0
 30 28  1  0
 18 16  2  0
 11  5  2  0
 20 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA140071

   N-[4-(2-Fluoro-5-trifluoromethyl-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzenesulfonamide

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: 462.45

Molecular Weight (Monoisotopic): 462.0331

AlogP: 4.79

#Rotatable Bonds: 6

Polar Surface Area: 77.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.75

CX Basic pKa: ┄

CX LogP: 4.54

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: -1.94

References

1. Röver S, Cesura AM, Huguenin P, Kettler R, Szente A..  (1997)  Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high-affinity inhibitors of kynurenine 3-hydroxylase.,  40  (26): [PMID:9435907] [10.1021/jm970467t]

Source

Source(1):

• Scientific Literature