4-(3-Pentafluorophenyl-ureido)-benzenesulfonamide

ID: ALA316779

Chembl Id: CHEMBL316779

PubChem CID: 11245996

Max Phase: Preclinical

Molecular Formula: C13H8F5N3O3S

Molecular Weight: 381.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 4-(3-(Perfluorophenyl)Ureido)Benzenesulfonamide | 4-{[(Pentafluorophenyl)Carbamoyl]Amino}Benzenesulfonamide | 4-{[(Pentafluorophenyl)carbamoyl]amino}benzenesulfonamide|CHEMBL316779|3n0n|SCHEMBL673008|IOSBUNBTXXXMFG-UHFFFAOYSA-N|BDBM50146756|4-(3-(Perfluorophenyl)Ureido)Benzenesulfonamide|4-(3-Pentafluorophenyl-ureido)-benzenesulfonamide|Q27464314|P9B

Canonical SMILES:  NS(=O)(=O)c1ccc(NC(=O)Nc2c(F)c(F)c(F)c(F)c2F)cc1

Standard InChI:  InChI=1S/C13H8F5N3O3S/c14-7-8(15)10(17)12(11(18)9(7)16)21-13(22)20-5-1-3-6(4-2-5)25(19,23)24/h1-4H,(H2,19,23,24)(H2,20,21,22)

Standard InChI Key:  IOSBUNBTXXXMFG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA316779

   4-{[(Pentafluorophenyl)carbamoyl]amino}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: 381.28

Molecular Weight (Monoisotopic): 381.0207

AlogP: 2.67

#Rotatable Bonds: 3

Polar Surface Area: 101.29

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.34

CX Basic pKa: ┄

CX LogP: 2.44

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: -1.62

References

1. de Leval X, Ilies M, Casini A, Dogné JM, Scozzafava A, Masini E, Mincione F, Starnotti M, Supuran CT..  (2004)  Carbonic anhydrase inhibitors: synthesis and topical intraocular pressure lowering effects of fluorine-containing inhibitors devoid of enhanced reactivity.,  47  (11): [PMID:15139757] [10.1021/jm031116j]

2. 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]

3. 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]

4. 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