3-(1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-4H-1λ6,2,4-benzothiadiazine-1,1-dione

• ChemBase ID: 163424
• Molecular Formular: C20H19N3O4S
• Molecular Mass: 397.44756
• Monoisotopic Mass: 397.1096271
• SMILES: c1ccc2c(c1)n(c(=O)c(c2O)C1=NS(=O)(=O)c2c(N1)cccc2)CCCC
• Canonical SMILES: CCCCn1c(=O)c(C2=NS(=O)(=O)c3c(N2)cccc3)c(c2c1cccc2)O
• InChI: InChI=1S/C20H19N3O4S/c1-2-3-12-23-15-10-6-4-8-13(15)18(24)17(20(23)25)19-21-14-9-5-7-11-16(14)28(26,27)22-19/h4-11,24H,2-3,12H2,1H3,(H,21,22)
• InChIKey: NQKPXUGRVIESOZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(1-butyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)-4H-1λ^6,2,4-benzothiadiazine-1,1-dione
• IUPAC Traditional name: 3-(1-butyl-4-hydroxy-2-oxoquinolin-3-yl)-4H-1λ^6,2,4-benzothiadiazine-1,1-dione
• Synonyms: 1-Butyl-3-(1,1-dioxido-2H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-2(1H)-quinolinone

Database IDs

• CAS Number: 303776-83-2
• PubChem SID: 162257559
• PubChem CID: 6258714

CALCULATED PROPERTIES

• Acid pKa: 6.4137783
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.1886582
• LogD (pH = 7.4): 1.2105623
• Log P: 2.2385912
• Molar Refractivity: 107.6276 cm^3
• Polarizability: 40.85385 Å^3
• Polar Surface Area: 99.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B691765

Heterocyclic inhibitor of the RNA-dependent RNA polymerase enzyme transcribed by the Hepatitis C virus.

REFERENCES

• Mashino, T., et al.: Bioorg. Med. Chem. Lett., 15, 1107 (2005)
• Liu, Y., et al.: Biochem., 45, 11312 (2005)
• Tedesco, R., et al.: J. Med. Chem., 49, 971 (2005)