2-(2,1,3-benzothiadiazole-4-sulfonamido)-5-chloro-N-(3,4-dichlorophenyl)benzamide

• ChemBase ID: 179789
• Molecular Formular: C19H11Cl3N4O3S2
• Molecular Mass: 513.80464
• Monoisotopic Mass: 511.93381527
• SMILES: S(=O)(=O)(c1c2nsnc2ccc1)Nc1c(C(=O)Nc2cc(c(cc2)Cl)Cl)cc(cc1)Cl
• Canonical SMILES: Clc1ccc(c(c1)C(=O)Nc1ccc(c(c1)Cl)Cl)NS(=O)(=O)c1cccc2c1nsn2
• InChI: InChI=1S/C19H11Cl3N4O3S2/c20-10-4-7-15(12(8-10)19(27)23-11-5-6-13(21)14(22)9-11)26-31(28,29)17-3-1-2-16-18(17)25-30-24-16/h1-9,26H,(H,23,27)
• InChIKey: JAEDBTTYEUJZJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,1,3-benzothiadiazole-4-sulfonamido)-5-chloro-N-(3,4-dichlorophenyl)benzamide
• IUPAC Traditional name: 2-(2,1,3-benzothiadiazole-4-sulfonamido)-5-chloro-N-(3,4-dichlorophenyl)benzamide
• Synonyms: Triclazan

Database IDs

• PubChem SID: 164235699
• PubChem CID: 1380896

CALCULATED PROPERTIES

• Acid pKa: 6.1986847
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.43913
• LogD (pH = 7.4): 4.7295732
• Log P: 5.5085588
• Molar Refractivity: 123.3205 cm^3
• Polarizability: 48.04985 Å^3
• Polar Surface Area: 101.05 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Putative type III secretion inhibitor in Yersinia

Product Information

• Application(s): Anthelmintic; Antiseptic

REFERENCES

• Kauppi AM,Andersson CD,Norberg HA,Sundin C,Linusson A,Elofsson M (2007)
• Inhibitors of type III secretion in Yersinia: design, synthesis and multivariate QSAR of 2-arylsulfonylamino-benzanilides.
• Bioorganic & medicinal chemistry 15, 6994-7011