3-{[(4-aminophenyl)sulfonyl]amino}benzenesulfonamide

ID: ALA14182

Chembl Id: CHEMBL14182

Cas Number: 16840-26-9

PubChem CID: 10663960

Max Phase: Preclinical

Molecular Formula: C12H13N3O4S2

Molecular Weight: 327.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(S(=O)(=O)Nc2cccc(S(N)(=O)=O)c2)cc1

Standard InChI:  InChI=1S/C12H13N3O4S2/c13-9-4-6-11(7-5-9)21(18,19)15-10-2-1-3-12(8-10)20(14,16)17/h1-8,15H,13H2,(H2,14,16,17)

Standard InChI Key:  BYERREGDQUCYJP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA14182

   4-amino-N-(3-sulfamoylphenyl)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: 327.39

Molecular Weight (Monoisotopic): 327.0347

AlogP: 0.72

#Rotatable Bonds: 4

Polar Surface Area: 132.35

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.21

CX Basic pKa: 2.08

CX LogP: 0.24

CX LogD: 0.18

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.71

Np Likeness Score: -1.78

References

1. Scozzafava A, Supuran CT..  (2000)  Carbonic anhydrase inhibitors: synthesis of N-morpholylthiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV.,  10  (10): [PMID:10843231] [10.1016/s0960-894x(00)00178-5]

2. Scozzafava A, Briganti F, Ilies MA, Supuran CT..  (2000)  Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes.,  43  (2): [PMID:10649985] [10.1021/jm990479+]

3. Scozzafava A, Briganti F, Mincione G, Menabuoni L, Mincione F, Supuran CT..  (1999)  Carbonic anhydrase inhibitors: synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route.,  42  (18): [PMID:10479300] [10.1021/jm9901879]

4. Agrawal VK, Singh J, Khadikar PV, Supuran CT..  (2006)  QSAR study on topically acting sulfonamides incorporating GABA moieties: a molecular connectivity approach.,  16  (7): [PMID:16458003] [10.1016/j.bmcl.2005.08.071]

5. Sethi KK, Verma SM, Prasanthi N, Sahoo SK, Parhi RN, Suresh P..  (2010)  3D-QSAR study of benzene sulfonamide analogs as carbonic anhydrase II inhibitors.,  20  (10): [PMID:20443227] [10.1016/j.bmcl.2010.03.104]

6. Vullo D, Luca VD, Scozzafava A, Carginale V, Rossi M, Supuran CT, Capasso C..  (2013)  The alpha-carbonic anhydrase from the thermophilic bacterium Sulfurihydrogenibium yellowstonense YO3AOP1 is highly susceptible to inhibition by sulfonamides.,  21  (6): [PMID:22883029] [10.1016/j.bmc.2012.07.024]

Source

Source(1):

• Scientific Literature