1048371-03-4

Basic information

• Product Name: 5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one
• Synonyms: 5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one;UPF 1069;5-(2-Oxo-2-phenylethoxy)-1(2H)-isoquinolinone;1(2H)-Isoquinolinone, 5-(2-oxo-2-phenylethoxy)-;UPF1069/UPF-1069
• CAS NO: 1048371-03-4
• Molecular Formula: C17H13NO3
• Molecular Weight: 281
• Product Categories: Inhibitor;Inhibitors
• Mol File: 1048371-03-4.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Storage Temp.: Store at RT
• Solubility: Soluble in DMSO (up to 40 mg/ml).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
• CAS DataBase Reference: 5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one(1048371-03-4)
• EPA Substance Registry System: 5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one(1048371-03-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 1048371-03-4(Hazardous Substances Data)

Usage

Description

5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one is a chemical compound that belongs to the isoquinolinone family. It is characterized by the presence of a phenylethoxy group attached to the 5-position of the isoquinolinone core, which contributes to its unique chemical properties and potential applications.

Uses

Used in Pharmaceutical Industry:
5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one is used as a selective PARP-2 inhibitor for its potential therapeutic applications in various diseases. Its high selectivity for PARP-2 (IC50=0.3 μM) and ~27-fold selectivity against PARP-1 make it a promising candidate for targeted therapies.
Used in Neuroprotection:
In the context of neuroprotection, 5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one has been shown to increase apoptosis in hippocampal slices, which could be beneficial in certain neurological conditions. Additionally, it protects cortical cells in models of post-ischemic brain damage, suggesting its potential use in treating stroke and other ischemic injuries.
Used in Cancer Therapy:
5-(2-Oxo-2-phenylethoxy)-3,4-dihydroisoquinolin-1(2H)-one has demonstrated its ability to block the interaction between PARP-2 and FOXA1, which in turn attenuates androgen receptor-mediated gene expression. This action leads to the inhibition of androgen receptor-positive prostate cancer growth, making it a potential therapeutic agent for the treatment of prostate cancer.

References

1) Pellicciari?et al.?(2008),?On the way to selective PARP-2 inhibitors. Design, synthesis, and preliminary evaluation of a series of isoquinolinone derivatives; Chem. Med. Chem.,?3?914 2) Thorsell?et al.?(2017),?Structural Basis for Potency and Promiscuity in Poly(ADP-ribose) Polymerase (PARP) and Tankyrase Inhibitors; J. Med. Chem.,?60?1262 3) Moroni?et al.?(2009),?Selective PARP-2 inhibitors increase apoptosis in hippocampal slices but protect cortical cells in models of post-ischaemic brain damage; Br. J. Pharmacol.,?157?854 4) Gui?et al.?(2019),?Selective targeting of PARP-2 inhibits androgen receptor signaling and prostate cancer growth through disruption of FOXA1 function; Proc. Natl. Acad. Sci. USA,?116?14573