128502-56-7

Usage

Uses

Used in Pharmaceutical Industry:
L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is used as a histone deacetylases (HDACs) inhibitor for its potential role in the development of novel therapeutics targeting various diseases, including cancer. HDACs are enzymes that remove acetyl groups from an ε-N-acetyl lysine amino acid on the histones, which leads to the tightening of DNA and decreased gene expression. Inhibiting HDACs can result in the relaxation of chromatin and increased gene expression, which may have therapeutic benefits.
Additionally, L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is used in the design of boronic acid-based autotaxin inhibitors. Autotaxin is an enzyme involved in the regulation of lysophosphatidic acid (LPA) levels, which has been implicated in various pathological conditions, including cancer, fibrosis, and inflammatory diseases. Inhibiting autotaxin can potentially reduce LPA levels and provide therapeutic benefits in these conditions.
Used in Chemical Research:
L-7-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid is also used as a research compound in the field of medicinal chemistry. Its unique chemical properties make it a valuable tool for studying the structure-activity relationships of various biologically active molecules and for the development of new drugs targeting specific enzymes or receptors.

InChI:InChI=1/C10H11NO3/c12-8-2-1-6-4-9(10(13)14)11-5-7(6)3-8/h1-3,9,11-12H,4-5H2,(H,13,14)

Upstream product

• 109-87-5 Dimethoxymethane 
• 60-18-4 L-tyrosine 
• 300-39-0 3,5-diiodo-l-tyrosine 
• 142335-40-8 (S)-1,2,3,4-Tetrahydro-7-hydroxy-6,8-diiodoisoquinoline-3-carboxylic acid 

Downstream Products

• 201413-65-2 (3S)-N-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid 
• 201413-66-3 methyl (3S)-N-benzyloxycarbonyl-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylate 
• 1312201-56-1 (S)-2-(4-fluorobenzyl)-7-hydroxy-10,10a-dihydroimidazo-[1,5-b]isoquinoline-1,3(2H,5H)-dione 
• 1312201-58-3 (S)-(4-(((2-(4-fluorobenzyl)-1,3-dioxo-1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolin-7-yl)oxy)methyl)phenyl)boronic acid 
• 142335-42-0 (3S)-2-(tert-butoxycarbonyl)-7-hydroxy-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid 

Relevant academic research and scientific papers

Discovery of potent heterodimeric antagonists of inhibitor of apoptosis proteins (IAPs) with sustained antitumor activity

The prominent role of IAPs in controlling cell death and their overexpression in a variety of cancers has prompted the development of IAP antagonists as potential antitumor therapies. We describe the identification of a series of heterodimeric antagonists with highly potent antiproliferative activities in cIAP- and XIAP-dependent cell lines. Compounds 15 and 17 further demonstrate curative efficacy in human melanoma and lung cancer xenograft models and are promising candidates for advanced studies.

A facile synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid, a conformationally constrained tyrosine analogue

A rapid synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid is given. Pictet-Spengler reaction on diiodo- or dibromo-substituted tyrosine (3-(3,5-dihalo-4-hydroxyphenyl)-2-aminopropanoic acid), followed by catalytic dehalogenation gives the desired compound in high optical purity.

PROTEOLYSIS-TARGETING CHIMERAS

The present disclosure provides compounds of the formula (I) wherein these compounds contain a ligand which binds to one or more target proteins such as CDK4 or CDK6 and a ligand which binds to the machinery associated with the ubiquitinating protein machinery. Also provided herein are methods of using these compounds in compositions or methods of treating patients with these compounds for the treatment of a disease or disorders such as cancer.

NOVEL BENZODIAZEPINE DERIVATIVES AND USES THEREOF

The present disclosure provides compounds and compositions capable of extending lifespan, and methods of use thereof.

IAP ANTAGONISTS

There are disclosed compounds that modulate the activity of inhibitors of apoptosis (IAPs), pharmaceutical compositions containing said compounds and methods of treating proliferative disorders and disorders of dysregulated apoptosis, such as cancer, utilizing the compounds of the invention.

Design, synthesis and preliminary activity assay of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as novel Histone deacetylases (HDACs) inhibitors

Histone deacetylases (HDACs) are enzymes involved in tumor genesis and development. Herein, we report a novel series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as HDACs inhibitors. The preliminary biological screening showed that most