ID: ALA379206

Max Phase: Preclinical

Molecular Formula: C12H11N3O3S

Molecular Weight: 277.31

Molecule Type: Small molecule

Representations

Synonyms (2): 4-((4-Hydroxyphenyl)Diazenyl)Benzenesulfonamide | 4-(4'-Hydroxyphenyl)Diazenylbenzenesulfonamide
Synonyms from Alternative Forms(2):

Canonical SMILES:  NS(=O)(=O)c1ccc(/N=N/c2ccc(O)cc2)cc1

Standard InChI:  InChI=1S/C12H11N3O3S/c13-19(17,18)12-7-3-10(4-8-12)15-14-9-1-5-11(16)6-2-9/h1-8,16H,(H2,13,17,18)/b15-14+

Standard InChI Key:  IPPFWRRJWLCWGK-CCEZHUSRSA-N

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

Properties

Molecular Weight: 277.31

Molecular Weight (Monoisotopic): 277.0521

AlogP: 2.46

#Rotatable Bonds: 3

Polar Surface Area: 105.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.91

CX Basic pKa: 0.42

CX LogP: 2.68

CX LogD: 2.56

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.84

Np Likeness Score: -0.77

References

1. Tsai WJ, Shiao YJ, Lin SJ, Chiou WF, Lin LC, Yang TH, Teng CM, Wu TS, Yang LM..  (2006)  Selective COX-2 inhibitors. Part 1: synthesis and biological evaluation of phenylazobenzenesulfonamides.,  16  (17): [PMID:16814546] [10.1016/j.bmcl.2006.06.036]

2. Maresca A, Carta F, Vullo D, Scozzafava A, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Inhibition of the Rv1284 and Rv3273 beta-carbonic anhydrases from Mycobacterium tuberculosis with diazenylbenzenesulfonamides.,  19  (17): [PMID:19651511] [10.1016/j.bmcl.2009.07.088]

3. Carta F, Maresca A, Scozzafava A, Vullo D, Supuran CT..  (2009)  Carbonic anhydrase inhibitors. Diazenylbenzenesulfonamides are potent and selective inhibitors of the tumor-associated isozymes IX and XII over the cytosolic isoforms I and II.,  17  (20): [PMID:19773173] [10.1016/j.bmc.2009.09.003]

4. PubChem BioAssay data set, 

5. De Luca L, Ferro S, Damiano FM, Supuran CT, Vullo D, Chimirri A, Gitto R..  (2014)  Structure-based screening for the discovery of new carbonic anhydrase VII inhibitors.,  71  [PMID:24287559] [10.1016/j.ejmech.2013.10.071]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays