22446-41-9

Basic information

• Product Name: 3-hydroxyphenylacetamide
• Synonyms: 3-Hydroxybenzeneacetamide;m-Hydroxyphenylacetamide
• CAS NO: 22446-41-9
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 22446-41-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-hydroxyphenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxyphenylacetamide(22446-41-9)
• EPA Substance Registry System: 3-hydroxyphenylacetamide(22446-41-9)

Safety Data

• Hazardous Substances Data: 22446-41-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxyphenylacetamide is used as a key intermediate in the synthesis of [18F]Maleimide-based Glycogen synthase kinase-3β (GSK-3β) ligands. These ligands are specifically designed for use in positron emission tomography (PET) imaging, a non-invasive diagnostic technique that allows for the visualization of molecular processes within the body.
In the context of PET imaging, 3-hydroxyphenylacetamide plays a crucial role in the development of radiotracers that can selectively bind to GSK-3β, a protein kinase involved in various cellular processes, including glycogen synthesis, cell cycle regulation, and gene expression. Abnormalities in GSK-3β activity have been implicated in several neurological disorders, such as Alzheimer's disease and bipolar disorder, making it an important target for diagnostic and therapeutic interventions.
By incorporating 3-hydroxyphenylacetamide into the structure of [18F]Maleimide-based GSK-3β ligands, researchers can create radiotracers that exhibit high affinity and selectivity for GSK-3β. This enables the PET imaging technique to detect and monitor the activity of this enzyme in vivo, providing valuable insights into the underlying mechanisms of diseases associated with GSK-3β dysregulation and guiding the development of targeted therapies.

InChI:InChI=1S/C8H9NO2/c9-8(11)5-6-2-1-3-7(10)4-6/h1-4,10H,5H2,(H2,9,11)

Upstream product

• 42058-59-3 3-hydroxy-benzeneacetic acid, methyl ester 
• 22446-38-4 ethyl 3-hydroxyphenylacetate 
• 621-37-4 m-hydroxyphenylacetic acid 

Downstream Products

• 868697-61-4 C₃₁H₃₂N₃O₇P 

Relevant articles and documents

[18F]MALEIMIDE-BASED GLYCOGEN SYNTHASE KINASE-3BETA LIGANDS FOR POSITRON EMISSION TOMOGRAPHY IMAGING AND RADIOSYNTHESIS METHOD

The present invention provides a compound having the structure: (Formula I), and a method of inhibiting Glycogen synthase kinase-3 β (GSK-3β) in a subject comprising administering to the subject said compound, so as to thereby inhibit the GSK-3β in the subject.

Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging

Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.

Phosphonate-based irreversible inhibitors of human γ-glutamyl transpeptidase (GGT). GGsTop is a non-toxic and highly selective inhibitor with critical electrostatic interaction with an active-site residue Lys562 for enhanced inhibitory activity

γ-Glutamyl transpeptidase (GGT, EC 2.3.2.2) that catalyzes the hydrolysis and transpeptidation of glutathione and its S-conjugates is involved in a number of physiological and pathological processes through glutathione metabolism and is an attractive phar

3,4-DISUBSTITUTED MALEIMIDES FOR USE AS VASCULAR DAMAGING AGENTS

This invention relates to novel compounds of Formula (I) for use as vascular damaging agents: Formula (I) wherein Rl, R7, R8, R9, ARI, AR2, AR3, p, q and r are as described in the specification. The invention also relates to methods for preparing compounds of Formula (I), to their use as medicaments (including methods for the treatment of angiogenesis or disease states associated with angiogenesis) and to pharmaceutical compositions containing compounds of Formula (I).