4-(3-(3-nitrophenyl)ureido)benzenesulfonamide

ID: ALA1614844

Chembl Id: CHEMBL1614844

PubChem CID: 50909907

Max Phase: Preclinical

Molecular Formula: C13H12N4O5S

Molecular Weight: 336.33

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-{[(3'-Nitrophenyl)Carbamoyl]Amino}Benzenesulfonamide | 4-{[(3-Nitrophenyl)carbamoyl]amino}benzenesulfonamide|CHEMBL1614844|4-{[(3'-Nitrophenyl)Carbamoyl]Amino}Benzenesulfonamide|AYX|3n2p|SCHEMBL672979|MTGVDZIMBQRGPD-UHFFFAOYSA-N|BDBM50334349|4-(3-(3-nitrophenyl)ureido)benzenesulfonamide|Q27458130|4-{[(3''-Nitrophenyl)carbamoyl]amino}benzenesulfonamide

Canonical SMILES:  NS(=O)(=O)c1ccc(NC(=O)Nc2cccc([N+](=O)[O-])c2)cc1

Standard InChI:  InChI=1S/C13H12N4O5S/c14-23(21,22)12-6-4-9(5-7-12)15-13(18)16-10-2-1-3-11(8-10)17(19)20/h1-8H,(H2,14,21,22)(H2,15,16,18)

Standard InChI Key:  MTGVDZIMBQRGPD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1614844

   4-{[(3-Nitrophenyl)carbamoyl]amino}benzenesulfonamide

2. Alternative Forms:

   

   ALA1614844

   1-(3-nitrophenyl)-3-(4-sulfamoylphenyl)(11C)urea

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: 336.33

Molecular Weight (Monoisotopic): 336.0528

AlogP: 1.89

#Rotatable Bonds: 4

Polar Surface Area: 144.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.16

CX Basic pKa: ┄

CX LogP: 1.66

CX LogD: 1.66

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -2.05

References

1. Pacchiano F, Carta F, Vullo D, Scozzafava A, Supuran CT..  (2011)  Inhibition of β-carbonic anhydrases with ureido-substituted benzenesulfonamides.,  21  (1): [PMID:21145236] [10.1016/j.bmcl.2010.11.064]

2. Pacchiano F, Carta F, McDonald PC, Lou Y, Vullo D, Scozzafava A, Dedhar S, Supuran CT..  (2011)  Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.,  54  (6): [PMID:21361354] [10.1021/jm101541x]

3. Vullo D, Leewattanapasuk W, Mühlschlegel FA, Mastrolorenzo A, Capasso C, Supuran CT..  (2013)  Carbonic anhydrase inhibitors: inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with sulfonamides, sulfamates and sulfamides.,  23  (9): [PMID:23511020] [10.1016/j.bmcl.2013.02.092]

4. Güzel-Akdemir O, Biswas S, Lastra K, McKenna R, Supuran CT..  (2013)  Structural study of the location of the phenyl tail of benzene sulfonamides and the effect on human carbonic anhydrase inhibition.,  21  (21): [PMID:24012377] [10.1016/j.bmc.2013.08.011]

5. Lomelino CL, Mahon BP, McKenna R, Carta F, Supuran CT..  (2016)  Kinetic and X-ray crystallographic investigations on carbonic anhydrase isoforms I, II, IX and XII of a thioureido analog of SLC-0111.,  24  (5): [PMID:26810836] [10.1016/j.bmc.2016.01.019]

Source

Source(1):

• Scientific Literature