420849-22-5

Basic information

• Product Name: TIQ-A
• Synonyms: Thieno[2,3-c]isoquinolin-5(4H)-one
• CAS NO: 420849-22-5
• Molecular Formula: C11H7NOS
• Molecular Weight: 201.248
• Product Categories: Inhibitors
• Mol File: 420849-22-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 256-258°C
• Boiling Point: 282.167°C at 760 mmHg
• Flash Point: 124.451°C
• Appearance: /solid
• Density: 1.359g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.675
• Storage Temp.: 2-8°C
• Solubility: DMSO: 16 mg/mL, soluble
• PKA: 13.04±0.20(Predicted)
• CAS DataBase Reference: TIQ-A(CAS DataBase Reference)
• NIST Chemistry Reference: TIQ-A(420849-22-5)
• EPA Substance Registry System: TIQ-A(420849-22-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• WGK Germany: 3
• Hazardous Substances Data: 420849-22-5(Hazardous Substances Data)

Usage

Description

TIQ-A, also known as a potent PARP inhibitor, is a cell permeable compound with an IC50 of 450nM. It is characterized by its dark brown solid appearance and has demonstrated neuroprotective properties against oxygen-glucose deprivation injury in both in vitro and in vivo models.

Uses

Used in Pharmaceutical Industry:
TIQ-A is used as a potent PARP inhibitor for its neuroprotective effects against oxygen-glucose deprivation injury. It has shown to be effective in cultured murine cortical cells with an IC50 of 150nM and in rat transient focal ischemia model with a dosage of 3 mg/kg intraperitoneally.
Used in Research Applications:
TIQ-A is used as a research tool for studying the role of PARP in various cellular processes and its potential therapeutic applications in conditions involving oxidative stress and neurodegenerative diseases.

InChI:InChI=1/C11H7NOS/c13-10-8-4-2-1-3-7(8)9-5-6-14-11(9)12-10/h1-6H,(H,12,13)

Upstream product

• 10341-88-5 3-phenyl-thiophen-2-carboxylic acid 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

Continuous flow synthesis of thieno[2,3-c ]isoquinolin-5(4 H)-one scaffold: A valuable source of PARP-1 inhibitors

An efficient multistep method for the continuous flow synthesis of thieno[2,3-c]isoquinolin-5(4H)-one-A (TIQ-A), an important pharmacological tool and building block for PARP-1 inhibitors, has been developed. The synthesis involves a Suzuki coupling reaction to generate 3-phenylthiophene-2-carboxylic acid which is transformed into the corresponding acyl azide and readily cyclized by a thermal Curtius rearrangement. A statistical design of experiments (DoE) was employed as a valuable support for decision-making of further experiments enabling the development of a robust and reliable protocol for large-scale preparation. As a result, the reactions are facile, safe, and easy to scale-up. The large-scale applicability of this improved flow method was tested by conducting the reactions on multigram scale to produce the desired product in high yield and quality for biopharmacological appraisals.

Towards new neuroprotective agents: Design and synthesis of 4H-thieno[2,3-c] isoquinolin-5-one derivatives as potent PARP-1 inhibitors

An excessive activation of poly(ADP-ribose) polymerase-1 (PARP-1), a nuclear enzyme able to catalyze the transfer of ADP-ribose from NAD to acceptor proteins, is involved in the progression of neuronal damage after brain insult. Potent and selective PARP-