129075-49-6

Usage

Uses

Used in Pharmaceutical Research:
5-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE is used as a research compound for exploring its potential as a pharmaceutical agent, particularly in the field of neuroscience. Its activity as an NMDA receptor antagonist makes it a candidate for studying its effects on cognitive functions such as learning and memory.
Used in Neuroscience Applications:
In the neuroscience industry, 5-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE is used as a research tool to investigate its role in modulating NMDA receptor activity, which could have implications for the treatment of neurological disorders associated with cognitive impairment.
Used in Dopamine Receptor Research:
5-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE is also used in research focused on dopamine receptor antagonism, which may provide insights into its potential applications in treating conditions related to dopamine dysregulation, such as Parkinson's disease or addiction.

InChI:InChI=1/C10H11NO2/c1-13-9-4-2-3-8-7(9)5-6-11-10(8)12/h2-4H,5-6H2,1H3,(H,11,12)

Upstream product

• 258882-54-1 N-(methoxycarbonyl)-2-(2-methoxyphenyl)ethylamine 
• 56469-02-4 3,4-dihydro-5-hydroxy-1(2H)-isoquinolinone 
• 333-27-7 methyl trifluoromethanesulfonate 
• 103205-24-9 4-methoxy-1-indanone oxime 
• 13336-31-7 4-methoxylindanone 
• 40731-98-4 4-hydroxy-2,3-dihydroindan-1-one 
• 74-88-4 methyl iodide 
• 2045-79-6 o-methoxy-2-phenylethylamine 

Downstream Products

• 103030-70-2 5-methoxy-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

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.

Structure-Based Design and Discovery of New M2 Receptor Agonists

Muscarinic receptor agonists are characterized by apparently strict restraints on their tertiary or quaternary amine and their distance to an ester or related center. On the basis of the active state crystal structure of the muscarinic M2 receptor in complex with iperoxo, we explored potential agonists that lacked the highly conserved functionalities of previously known ligands. Using structure-guided pharmacophore design followed by docking, we found two agonists (compounds 3 and 17), out of 19 docked and synthesized compounds, that fit the receptor well and were predicted to form a hydrogen-bond conserved among known agonists. Structural optimization led to compound 28, which was 4-fold more potent than its parent 3. Fortified by the discovery of this new scaffold, we sought a broader range of chemotypes by docking 2.2 million fragments, which revealed another three micromolar agonists unrelated either to 28 or known muscarinics. Even pockets as tightly defined and as deeply studied as that of the muscarinic reveal opportunities for the structure-based design and the discovery of new chemotypes.

17a-HYDROXYLASE/C17,20-LYASE INHIBITORS

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

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.

17α-HYDROXYLASE/C17,20-LYASE INHIBITORS

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

CYCLOHEXYL AMIDE DERIVATIVES AS CRF RECEPTOR ANTAGONISTS

There are described cydohexyl amide derivatives useful as corticotropin releasing factor (CRF) receptor antagonists

A study on the conversion of indanones into carbostyrils

We have surveyed the utility of Beckmann rearrangement for the conversion of indanones into carbostyrils. Initial attempts at the conversion of 6-methoxy indanone oxime under classical conditions resulted in the formation of the two unusual products: 2-sulfonyloxyindanone and the dimeric product. This unusual rearrangement was also observed by the treatment of some metal triflates species. Further investigation has led to the development of reliable conditions starting from oxime mesylate (not oxime tosylate), in which some strong Lewis acid catalyst (ZrCl4) was employed in either a conventional or non-conventional solvent system. The advantage of the new protocol is highlighted by the simple work up and direct isolation of the product in 65% isolated yield.

Interesting reaction of the indanone oximes under Beckmann rearrangement conditions

Attempted Beckmann rearrangement of the 6-methoxyindanone oximes in conventional conditions resulted in the formation of the two kinds of unexpected products: 2-sulfonyloxyindanone and the dimeric product. Related rearrangement was also observed in the re

A structure-affinity relationship study on derivatives of N-[2-[4-(4- chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide, a high-affinity and selective D4 receptor ligand

N-[2-[4-(4-Chlorophenyl)piperazin-1-yl]ethyl]-3-methoxybenzamide (1), a high-affinity and selective dopamine D4 receptor ligand, was chosen as a lead, and structural modifications were done on its amide bond and on its alkyl chain linking the b

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.