56469-02-4

Basic information

• Product Name: 5-HYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• Synonyms: 5-HYDROXY-1,2,3,4-TETRAHYDROISOQUINOLIN-1-ONE;5-HYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE;3,4-DIHYDRO-5-HYDROXY-1(2H)-ISOQUINOLINONE;5-hydroxy-3,4-dihydroisoquinolin-1(2H)-one
• CAS NO: 56469-02-4
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• Mol File: 56469-02-4.mol

Chemical Properties

• Boiling Point: 473.848 °C at 760 mmHg
• Flash Point: 240.375 °C
• Appearance: /
• Density: 1.282 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• PKA: 9.23±0.20(Predicted)
• CAS DataBase Reference: 5-HYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(56469-02-4)
• EPA Substance Registry System: 5-HYDROXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(56469-02-4)

Safety Data

• Hazardous Substances Data: 56469-02-4(Hazardous Substances Data)

Usage

Uses

5-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one is a useful research chemical.

InChI:InChI=1/C9H9NO2/c11-8-3-1-2-7-6(8)4-5-10-9(7)12/h1-3,11H,4-5H2,(H,10,12)

Upstream product

• 40731-98-4 4-hydroxy-2,3-dihydroindan-1-one 
• 5154-02-9 1,5-dihydroxy-1(2H)-isoquinoline 
• 5154-02-9 isoquinoline-1,5-diol 

Downstream Products

• 129075-49-6 3,4-dihydro-5-methoxy-1(2H)-isoquinolinone 
• 129075-87-2 3,4-dihydro-5-(3-chloropropoxy)-1(2H)-isoquinolinone 

Relevant articles and documents

Development of 3,4-dihydroisoquinolin-1(2H)-one derivatives for the Positron Emission Tomography (PET) imaging of σ2 receptors

σ2 Receptors are promising biomarkers for cancer diagnosis given the relationship between the proliferative status of tumors and their density. With the aim of contributing to the research of σ2 receptor Positron Emission Tomography (PET) probes, we developed 2-[3-[6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]propyl]-3, 4-dihydroisoquinolin-1(2H)-one (3), with optimal σ2 pharmacological properties and appropriate lipophilicity. Hence, 3 served as the lead compound for the development of a series of dihydroisoquinolinones amenable to radiolabeling. Radiosynthesis for compound 26, which displayed the most appropriate σ2 profile, was developed and σ2 specific binding for the corresponding [18F]-26 was confirmed by in vitro autoradiography on rat brain slices. Despite the excellent in vitro properties, [18F]-26 could not successfully image σ2 receptors in the rat brain in vivo, maybe because of its interaction with P-gp. Nevertheless, [18F]-26 may still be worthy of further investigation for the imaging of σ2 receptors in peripheral tumors devoid of P-gp overexpression.

Synthesis of 3,4-dihydro-1(2H)-isoquinolinones

Approaches toward the preparative-scale synthesis of target 3,4-dihydro-1(2H)-isoquinolinones 1-3 are presented. Compounds 1 and 2 were prepared via a Schmidt rearrangement on easily obtained indanone precursors, but in low overall yield. A better method

Synthesis of 3,4-dihydro-5-[11C]methoxy-1(2H)-isoquinolinone as a Potential Tracer for Poly(ADP-ribose) Synthetase

Synthesis of 3,4-dihydro-5-[11C]methoxy-1(2H)-isoquinolinone ([11C]MIQO), a potent poly (ADP-ribose) synthetase inhibitor, was devised in order to evaluate whether it is possible to image excessive activation of poly(ADP-ribose) synthetase (PARS) by positron emission tomography. [11C]MIQO was prepared by O-[11C]methylation of 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone, obtained by a Schmidt reaction with 4-hydroxy-1-indanone, sodium azide and trichloroacetic acid, with [11C]methyl triflate. Total synthesis time from EOB was 35 minutes. The radiochemical yield based on [11C]carbon dioxide was 31 +/- 8 percent (n=8; decay corrected). The final product had a specific activity of 76 GBq/umol at EOS, and the radiochemical purity of [11C]MIQO was over 99 percent.

Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process

The invention is selected, novel, and known analogs of isoquinolinones of the formula and pharmaceutically acceptable salts thereof; novel pharmaceutical compositions; and a method for enhancing the lethal effects for tumor cells to treatment having DNA damaging activity such as ionizing radiation or with chemotherapeutic agents.

BICYCLIC NITROGEN HETEROCYCLIC ETHERS AND THIOETHERS, AND THEIR PHARMACEUTICAL USES

A class of bicyclic nitrogen heterocyclic ether and thioether compounds exhibiting pharmacological activity including cytoprotective, H. sub.2-antagonist, anti-secretory and anti-ulcerogenic activity, pharmaceutical compositions comprising these compounds, and methods for the treatment of gastrointestinal hyperacidity and ulcerogenic disorders in mammals using said compositions are disclosed.