4H,5H-thieno[2,3-c]isoquinolin-5-one

• ChemBase ID: 154287
• Molecular Formular: C11H7NOS
• Molecular Mass: 201.24438
• Monoisotopic Mass: 201.02483485
• SMILES: c1ccc2c(c1)c1ccsc1[nH]c2=O
• Canonical SMILES: O=c1[nH]c2sccc2c2c1cccc2
• InChI: InChI=1S/C11H7NOS/c13-10-8-4-2-1-3-7(8)9-5-6-14-11(9)12-10/h1-6H,(H,12,13)
• InChIKey: LQJVOLSLAFIXSV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4H,5H-thieno[2,3-c]isoquinolin-5-one
• IUPAC Traditional name: 4H-thieno[2,3-c]isoquinolin-5-one
• Synonyms: TIQ-A; Thieno[2,3-c]isoquinolin-5-one; TIQ-A

Database IDs

• CAS Number: 420849-22-5
• MDL Number: MFCD06407947
• PubChem SID: 162248426; 24724630
• PubChem CID: 9899130

CALCULATED PROPERTIES

• Acid pKa: 9.476169
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.6855044
• LogD (pH = 7.4): 2.6821005
• Log P: 2.685548
• Molar Refractivity: 56.9354 cm^3
• Polarizability: 22.227135 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble16 mg/mL
• Apperance: Dark Brownish Blue Solid; solid
• Melting Point: 256-258°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H7NOS

DETAILS

Sigma Aldrich - T2825

Biochem/physiol Actions
TIQ-A is a potent inhibitor of PARP, anti-apoptotic.

Toronto Research Chemicals - T445100

A cell permeable, potent PARP inhibitor with an IC50 of 450nM. Shown to be neuroprotective against oxygen-glucose deprivation injury in vitro in cultured murine cortical cells ( IC50 of 150nM) and in vivi in rat transient focal ischemia model (3 mg/kg i

REFERENCES

• Chiarugi, A., et al.: J. Pharmacol. Exp. Ther., 305, 43 (2003)
• pellicciari, R., et al.: Farmaco., 58, 851 (2003)