4456-77-3

Usage

Uses

Used in Pharmaceutical Development:
1,2,3,4-Tetrahydroisoquinoline-1,3-dione is used as a pharmaceutical precursor for its potential to be developed into new drugs, leveraging its antioxidant and anti-inflammatory properties for therapeutic applications.
Used in Organic Synthesis:
In the field of organic chemistry, 1,2,3,4-Tetrahydroisoquinoline-1,3-dione is used as an intermediate in the synthesis of various organic compounds, contributing to the creation of a wide range of chemical products.

InChI:InChI=1/C9H7NO2/c11-8-5-6-3-1-2-4-7(6)9(12)10-8/h1-4H,5H2,(H,10,11,12)

Upstream product

• 4476-30-6 2-carbamoylmethyl-benzoic acid 
• 3759-28-2 (2-cyanophenyl)acetonitrile 
• 89-51-0 Homophthalic acid 
• 95-50-1 1,2-dichloro-benzene 
• 201230-82-2 carbon monoxide 
• 76746-89-9 ethyl 3-methyl-1-oxo-1H-isochromene-4-carboxylate 
• 25113-15-9 methyl 3-methyl-1-oxo-1H-isochromene-4-carboxylate 
• 59048-59-8 2-carbamoylmethyl-benzoic acid methyl ester 
• 1033330-27-6 7-bromoisoquinoline-1,3(2H,4H)-dione 
• 179897-89-3 5-Bromo-2-fluoro-benzonitrile 
• 925672-89-5 5-bromo-2-(cyanomethyl)benzonitrile 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 103-82-2 phenylacetic acid 
• 1118-02-1 trimethylsilyl isocyanate 

Downstream Products

• 60813-44-7 4-phenylmethylene-1,2,3,4-tetrahydroisoquinoline-1,3-dione 
• 29777-47-7 4,4-dibenzyl-4H-isoquinoline-1,3-dione 
• 41058-61-1 Diallylhomophthalid 
• 119-65-3 isoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 5488-36-8 4,4-dimethyl-4H-isoquinoline-1,3-dione 
• 56055-60-8 4-Isonitroso-homophthalimid 
• 17247-29-9 4,4-Dibrom-1,3-dioxo-1,2,3,4-tetrahydroisochinolin 
• 4476-30-6 2-carbamoylmethyl-benzoic acid 
• 23362-56-3 Homophthalsaeuremonoamid-(1) 
• 38209-13-1 1-hydroxy-2-phenyl-5H-pyrano[2,3-c]isoquinoline-3,6-dione 
• 38324-88-8 2-benzyl-1-hydroxy-5H-pyrano[2,3-c]isoquinoline-3,6-dione 
• 76694-25-2 2-Chloro-3-(4'-homophthalimido)-1,4-naphthoquinone 
• 76694-26-3 12-(2'-carboxyamidophenyl)naphth<2,3-b>indolizine-6,11-dione 

Relevant academic research and scientific papers

4-benzylideneisoquinoline-1,3(2H,4H)-diones as tyrosyl DNA phosphodiesterase 2 (TDP2) inhibitors

Tyrosyl-DNA phosphodiesterase 2 (TDP2) repairs topoisomerase II (Top2) mediated DNA damages, including double-strand breaks (DSBs) that underpin the anticancer mechanism of clinical Top2 poisons such as etoposide (ETP). Inhibition of TDP2 could sensitize

FUSED-GLUTARIMIDE CRBN LIGANDS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same. The present invention also relates to compounds and methods useful for binding and modulating the activity of cereblon (CRBN), especially for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.

Enantioselective synthesis of isoquinoline-1,3(2: H,4 H)-dione derivatives via a chiral phosphoric acid catalyzed aza-Friedel-Crafts reaction

A highly enantioselective aza-Friedel-Crafts reaction of structurally new ketimines with indoles and pyrrole is developed by using a chiral phosphoric acid as the catalyst. This protocol enables the first enantioselective synthesis of isoquinoline-1,3(2H,

A Cu-Doped ZIF-8 metal organic framework as a heterogeneous solid catalyst for aerobic oxidation of benzylic hydrocarbons

Mixed-metal metal organic frameworks have received considerable attention in recent years and it has been shown that the activity of the parent metal organic framework (MOF) is often enhanced upon doping with external metal ions within the framework. In this context, Cu2+ ions with different loadings were incorporated within the ZIF-8 framework to obtain a series of Cu-doped ZIF-8 materials and their activity was examined in the aerobic oxidation of hydrocarbons. The as-synthesized Cu-doped solids were characterized by powder X-ray diffraction (XRD), ultraviolet diffuse reflectance spectroscopy (UV-DRS), scanning electron microscopy (SEM), Fourier Transform infrared (FT-IR), electron paramagnetic resonance (EPR) and inductively coupled plasma (ICP) analysis. The experimental results revealed that the activity of Cu-doped ZIF-8 is much higher than that of the parent ZIF-8 in all the tested substrates at 120 °C. Furthermore, the activity of the Cu-doped ZIF-8 with the highest Cu loading was eight fold higher than that of the parent ZIF-8 in the aerobic oxidation of cyclooctane (1) at 120 °C with more than 80% selectivity to the corresponding cyclooctanol/cyclooctanone (ol/one) mixture. Cu-doped ZIF-8 was reused two times with no significant drop in its activity under identical conditions. Furthermore, comparison of the two times reused solid with that of the fresh solid by powder XRD and SEM analysis revealed identical structural integrity and morphology, respectively during the oxidation reactions.

Superelectrophiles in Synthesis: Preparation of Aromatic Imides

Aromatic carboxylic acids are found to undergo reactions with isocyanates, wherein triflic acid promotes the formation of aromatic imide products in fair to good yields. It is proposed that the carboxylic acid group directs the isocyanate electrophile to

Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)-cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.

2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions

The synthesis of biologically relevant homophthalimide and 3-aminoisocoumarin nuclei via palladium-catalyzed carbonylation of 2-(2-iodoaryl)acetamides has been developed. The degree of N-substitution on the starting amide substrate dictates whether C?N or

Exploration of the nicotinamide-binding site of the tankyrases, identifying 3-arylisoquinolin-1-ones as potent and selective inhibitors in vitro

Tankyrases-1 and -2 (TNKS-1 and TNKS-2) have three cellular roles which make them important targets in cancer. Using NAD+ as a substrate, they poly(ADP-ribosyl)ate TRF1 (regulating lengths of telomeres), NuMA (facilitating mitosis) and axin (in wnt/β-catenin signalling). Using molecular modelling and the structure of the weak inhibitor 5-aminoiso quinolin-1-one, 3-aryl-5-substituted-isoquinolin-1-ones were designed as inhibitors to explore the structure-activity relationships (SARs) for binding and to define the shape of a hydrophobic cavity in the active site. 5-Amino-3-arylisoquinolinones were synthesised by Suzuki-Miyaura coupling of arylboronic acids to 3-bromo-1-methoxy-5-nitro-isoquinoline, reduction and O-demethylation. 3-Aryl-5-methylisoquinolin-1-ones, 3-aryl-5-fluoroisoquinolin-1-ones and 3-aryl-5-methoxyisoquinolin-1-ones were accessed by deprotonation of 3-substituted-N,N,2-trimethylbenzamides and quench with an appropriate benzonitrile. SAR around the isoquinolinone core showed that aryl was required at the 3-position, optimally with a para-substituent. Small meta-substituents were tolerated but groups in the ortho-positions reduced or abolished activity. This was not due to lack of coplanarity of the rings, as shown by the potency of 4,5-dimethyl-3-phenylisoquinolin-1-one. Methyl and methoxy were optimal at the 5-position. SAR was rationalised by modelling and by crystal structures of examples with TNKS-2. The 3-aryl unit was located in a large hydrophobic cavity and the para-substituents projected into a tunnel leading to the exterior. Potency against TNKS-1 paralleled potency against TNKS-2. Most inhibitors were highly selective for TNKSs over PARP-1 and PARP-2. A range of highly potent and selective inhibitors is now available for cellular studies.

DENGUE AND WEST NILE VIRUS PROTEASE INHIBITORS

Compounds and methods of treating or preventing a Flavivirus infection in a subject are provided. The methods comprise administering to the subject a therapeutically effective amount of a compound as described herein. The methods are useful in treating and/or preventing Flavivirus infections such as, for example, West Nile Virus, Dengue Virus, and Japanese Encephalitis Virus. Methods of inhibiting a Flavivirus protease in a cell are also provided.

Pyridine- and isoquinoline-derivatives as Syk and JAK kinase inhibitors

The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by inhibition of Syk kinase and/or Janus kinases.