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

ID: ALA136328

PubChem CID: 10407177

Max Phase: Preclinical

Molecular Formula: C15H12N4O4S2

Molecular Weight: 376.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(S(=O)(=O)Nc2nc(-c3cccc([N+](=O)[O-])c3)cs2)cc1

Standard InChI:  InChI=1S/C15H12N4O4S2/c16-11-4-6-13(7-5-11)25(22,23)18-15-17-14(9-24-15)10-2-1-3-12(8-10)19(20)21/h1-9H,16H2,(H,17,18)

Standard InChI Key:  SAJMJWKYJRZVSC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  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
    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
    1.3667   -3.7292    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
    1.8875   -2.8292    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
    5.5167   -2.5042    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
    6.0417   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -3.7042    0.0000 N   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   -3.7042    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   -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  9  1  0
  6  4  1  0
  7  3  1  0
  8  7  1  0
  9 14  2  0
 10  1  1  0
 11  6  1  0
 12  1  2  0
 13  1  2  0
 14 11  1  0
 15  5  1  0
 16  5  2  0
 17 10  1  0
 18 10  2  0
 19 22  2  0
 20 19  1  0
 21 17  2  0
 22 18  1  0
 23 25  2  0
 24 11  2  0
 25 24  1  0
 19 21  1  0
  8  6  2  0
  9 23  1  0
M  CHG  2   5   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA136328

   4-Amino-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: 376.42

Molecular Weight (Monoisotopic): 376.0300

AlogP: 3.10

#Rotatable Bonds: 5

Polar Surface Area: 128.22

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.91

CX Basic pKa: 2.13

CX LogP: 2.95

CX LogD: 2.47

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.40

Np Likeness Score: -2.16

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