3,4-Dichloro-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

ID: ALA136826

PubChem CID: 10526613

Max Phase: Preclinical

Molecular Formula: C15H9Cl2N3O4S2

Molecular Weight: 430.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cccc(-c2csc(NS(=O)(=O)c3ccc(Cl)c(Cl)c3)n2)c1

Standard InChI:  InChI=1S/C15H9Cl2N3O4S2/c16-12-5-4-11(7-13(12)17)26(23,24)19-15-18-14(8-25-15)9-2-1-3-10(6-9)20(21)22/h1-8H,(H,18,19)

Standard InChI Key:  SIXKRNBZGWCFKP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  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
    1.3667   -4.3292    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
    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
    2.4000   -1.9250    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
    1.3667   -3.7292    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
    5.5250   -3.7042    0.0000 C   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
    4.1167   -1.8417    0.0000 O   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
    0.8500   -4.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -4.6375    0.0000 O   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
    6.0375   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -4.3042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -3.7042    0.0000 Cl  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   -2.5292    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
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5 11  1  0
  6  4  1  0
  7  1  1  0
  8  3  1  0
  9  8  1  0
 10  7  2  0
 11 16  2  0
 12  6  1  0
 13 10  1  0
 14  1  2  0
 15  1  2  0
 16 12  1  0
 17  5  1  0
 18  5  2  0
 19 21  1  0
 20  7  1  0
 21 20  2  0
 22 13  1  0
 23 19  1  0
 24 26  2  0
 25 12  2  0
 26 25  1  0
 19 13  2  0
  9  6  2  0
 11 24  1  0
M  CHG  2   5   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA136826

   3,4-Dichloro-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-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: 430.29

Molecular Weight (Monoisotopic): 428.9412

AlogP: 4.83

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.71

CX Basic pKa: ┄

CX LogP: 4.99

CX LogD: 4.41

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.46

Np Likeness Score: -2.52

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