N-[4-(4-Chloro-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide

ID: ALA335326

PubChem CID: 10666499

Max Phase: Preclinical

Molecular Formula: C16H13ClN2O2S2

Molecular Weight: 364.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)Nc2nc(-c3ccc(Cl)cc3)cs2)cc1

Standard InChI:  InChI=1S/C16H13ClN2O2S2/c1-11-2-8-14(9-3-11)23(20,21)19-16-18-15(10-22-16)12-4-6-13(17)7-5-12/h2-10H,1H3,(H,18,19)

Standard InChI Key:  NHZJRACGGVBOLR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  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
    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   -2.8125    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
    1.8875   -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
    5.5167   -2.5042    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
    1.3667   -2.5292    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
    0.8500   -2.8292    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   -3.7042    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
    0.3292   -3.7292    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -3.7042    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  3  1  0
  7  6  1  0
  8  1  1  0
  9  1  2  0
 10  1  2  0
 11  5  1  0
 12  8  2  0
 13  8  1  0
 14 11  1  0
 15 11  2  0
 16 18  2  0
 17 14  2  0
 18 15  1  0
 19 13  2  0
 20 12  1  0
 21 19  1  0
 22 16  1  0
 23 21  1  0
 21 20  2  0
  7  5  2  0
 17 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA335326

   N-[4-(4-Chloro-phenyl)-thiazol-2-yl]-4-methyl-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: 364.88

Molecular Weight (Monoisotopic): 364.0107

AlogP: 4.57

#Rotatable Bonds: 4

Polar Surface Area: 59.06

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.78

CX Basic pKa: ┄

CX LogP: 4.95

CX LogD: 4.41

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.74

Np Likeness Score: -2.19

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]

2. Hitchin JR, Blagg J, Burke R, Burns S, Cockerill MJ, Fairweather EE, Hutton C, Jordan AM, McAndrew C, Mirza A, Mould D, Thomson GJ, Waddell I, Ogilvie DJ.  (2013)  Development and evaluation of selective, reversible LSD1 inhibitors derived from fragments,  4  (11): [10.1039/C3MD00226H]

Source

Source(1):

• Scientific Literature