22246-12-4

Usage

Uses

Used in Chemical Research and Experimentations:
6-Methoxy-3,4-dihydro-2H-isoquinolin-1-one is used as a chemical compound in chemical research and experimentations for its complex structure and properties. It is often utilized in organic chemistry for creating numerous pharmacological substances.
Used in Organic Chemistry:
6-Methoxy-3,4-dihydro-2H-isoquinolin-1-one is used as a building block in organic chemistry for the synthesis of various pharmacological substances. Its complex structure allows for the creation of a wide range of compounds with potential applications in the pharmaceutical industry.
Used in Pharmaceutical Industry:
6-Methoxy-3,4-dihydro-2H-isoquinolin-1-one is used as a precursor in the pharmaceutical industry for the development of new drugs. Its potential applications in creating pharmacological substances make it a valuable compound for research and development in this field.
Note: Since the specific biological activities, safety, and efficacy of 6-Methoxy-3,4-dihydro-2H-isoquinolin-1-one are not comprehensively studied and acknowledged yet, its uses in other industries or applications may be limited or require further research and validation.

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

Upstream product

• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 5111-70-6 5-methoxy-1-indanone 
• 33543-63-4 ethyl-N-<2-(3-methoxyphenyl)ethyl>-carbamate 
• 62334-10-5 1-isocyano-2-(3-methoxyphenyl)ethane 
• 75-09-2 dichloromethane 
• 74-85-1 ethene 
• 1293990-75-6 N-tert-pentanoyloxy-p-methoxybenzamide 
• 1190890-94-8 tert-butyl-N-[(3-methoxyphenyl)ethyl]carbamate 
• 110192-21-7 N-(methoxycarbonyl)-2-(3'-methoxyphenyl)ethylamine 
• 337913-25-4 phosphorus pentaoxide 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 163713-49-3 3-(3-Methoxy-phenyl)-propionyl azide 
• 40478-49-7 3-(3-methoxyphenyl)propanoyl chloride 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 

Downstream Products

• 645388-69-8 6-methoxy-2-phenyl-3,4-dihydroisoquinolin-1(2H)-one 
• 573674-53-0 6-methoxy-2-(3-methoxyphenyl)-3,4-dihydro-2H-isoquinolin-1-one 
• 645388-86-9 6-methoxy-2-(4-chlorophenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 645388-75-6 6-methoxy-2-(4-fluorophenyl)-3,4-dihydroisoquinolin-1(2H)-one 
• 645388-73-4 2-(p-methylphenyl)-6-methoxy-3,4-dihydroisoquinolin-1-one 
• 645388-93-8 2-(3-chloro-phenyl)-6-methoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 645388-92-7 2-(3-fluorophenyl)-6-methoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 645389-09-9 2-(3-dimethylamino-phenyl)-6-methoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 645388-88-1 2-(4-isopropylphenyl)-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one 
• 645389-03-3 2-(3-isopropylphenyl)-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one 
• 96719-60-7 1-(4-bromophenyl)-6-methoxy-2-phenyl-3,4-dihydro-1H-isoquinoline 
• 844431-65-8 1-(4-bromophenyl)-2-(3-fluorophenyl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 844431-64-7 1-(4-bromo-phenyl)-2-(4-fluoro-phenyl)-6-methoxy-1,2,3,4-tetrahydro-isoquinoline 
• 844431-66-9 1-(4-bromo-phenyl)-6-methoxy-2-(3-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinoline 

Relevant academic research and scientific papers

1-[2-(1-Cyclobutylpiperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]propan-1-one: a Histamine H3 Receptor Inverse Agonist with Efficacy in Animal Models of Cognition

A series of chemical optimizations, which was guided by in vitro affinity at histamine H3 receptor (H3R), modulation of lipophilicity, ADME properties and preclinical efficacy resulted in the identification of 1-[2-(1-cyclobutylpiperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]propan-1-one (45 e) as a potent and selective (Ki=4.0 nM) H3R inverse agonist. Dipsogenia induced by (R)-α-methylhistamine was dose dependently antagonized by 45 e, confirming its functional antagonism at H3R. It is devoid of hERG and phospholipidosis issues. Compound 45 e has adequate oral exposures and favorable half-life in both rats and dogs. It has demonstrated high receptor occupancy (ED80=0.22 mg/kg) and robust efficacy in object recognition task and, dose dependently increased acetylcholine levels in brain. The sub-therapeutic doses of 45 e in combination with donepezil significantly increased acetylcholine levels. The potent affinity, selectivity, in vivo efficacy and drug like properties together with safety, warrant for further development of this molecule for potential treatment of cognitive disorders associated with Alzheimer's disease.

Rhodium(III)-Catalyzed C-H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds

We describe a simple and robust procedure for the Rh(III)-catalyzed [4+2] cycloaddition of feedstock gases enabled through C-H activation. A diverse set of 3,4-dihydroisoquinolones and 3-methylisoquinolones have been prepared in good to excellent yields.

Easy Access to 2,4-Disubstituted Cyclopentenones by a Gold(III)-Catalyzed A3-Coupling/Cyclization Cascade

An efficient and convenient synthesis of 2,4-disubstituted cyclopentenones has been achieved through a Au(III)-catalyzed isomerization-A3-coupling/cyclization cascade. A possible mechanism involving an initial Au(III)-catalyzed isomerization, A3-type coupling, and cyclization via an enol intermediate is postulated.

FLUOROALLYLAMINE DERIVATIVE AND USE THEREOF

The present invention relates to a fluoroallylamine derivative and use thereof. In particular, the present invention relates to a compound as shown in Formula I, a prodrug, an isomer, an isotope-labeled compound, a solvate or a pharmaceutically acceptable salt thereof, which has VAP-1/SSAO inhibitory activity, and can be used for treating a disease associated with VAP-1/SSAO overactivity.

Discovery of 5-phenoxy-2-aminopyridine derivatives as potent and selective irreversible inhibitors of bruton’s tyrosine kinase

As a member of the tyrosine protein kinase Tec (TEC) family, Bruton’s tyrosine kinase (BTK) is considered a promising therapeutic target due to its crucial roles in the B cell receptor (BCR) signaling pathway. Although many types of BTK inhibitors have been reported, there is an unmet need to achieve selective BTK inhibitors to reduce side effects. To obtain BTK selectivity and efficacy, we designed a novel series of type II BTK inhibitors which can occupy the allosteric pocket induced by the DFG-out conformation and introduced an electrophilic warhead for targeting Cys481. In this article, we have described the structure-activity relationships (SARs) leading to a novel series of potent and selective piperazine and tetrahydroisoquinoline linked 5-phenoxy-2-aminopyridine irreversible inhibitors of BTK. Compound 18g showed good potency and selectivity, and its biological activity was evaluated in hematological tumor cell lines. The in vivo efficacy of 18g was also tested in a Raji xenograft mouse model, and it significantly reduced tumor size, with 46.8% inhibition compared with vehicle. Therefore, we have presented the novel, potent, and selective irreversible inhibitor 18g as a type II BTK inhibitor.

Isoquinolinone derivatives as potent CNS multi-receptor D2/5-HT1A/5-HT2A/5-HT6/5-HT7 agents: Synthesis and pharmacological evaluation

In this study, a series of novel Isoquinolinone derivatives were synthesized as potential multi-target antipsychotics. Among these, compound 13 showed high affinity for dopamine D2 and serotonin 5-HT1A, 5-HT2A, 5-HT6, and 5-HT7 receptors, showed low affinity for off-target receptors (5-HT2C, H1, and α1), and negligible effects on ether-a-gogo-related gene (hERG; i.e., reduced QT interval prolongation). An animal behavioral study revealed that compound 13 reversed APO-induced hyperlocomotion, MK-801-induced hyperactivity, and DOI-induced head twitch. Moreover, compound 13 exhibited a high threshold for acute toxicity, a lack of tendency to induce catalepsy, and did not cause prolactin secretion or weight gain when compared to risperidone. Furthermore, in the forced swim test, tail suspension test, and novel object recognition test, treatment with compound 13 resulted in improvements in depression and cognitive impairment. In addition, compound 13 had a favorable pharmacokinetic profile in rats. Thus, the antipsychotic drug-like effects of compound 13 indicate that it may be useful for developing a novel class of drugs for the treatment of schizophrenia.

INDOLINONE COMPOUNDS FOR USE AS MAP4K1 INHIBITORS

The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein ring A, ring C, X1, X2, L1, R1, R2, R3, R4, R5, R6, R7, m and n are as defined herein, which are useful as MAP4K1 inhibitors, processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by MAP4K1.

Quinoline and Isoquinoline Based HDAC Inhibitors and Methods of Use Thereof

The present invention relates to methods of modulating activity of histone deacetylases (HDACs). The present invention also relates to methods of treating HDAC-associated diseases including, but not limited to, cancers, inflammatory disorders, and neurode

Catalyst-free cyclization of anthranils and cyclic amines: One-step synthesis of rutaecarpine

An efficient synthesis of a variety of quinazolinone derivatives via a direct cyclization reaction between commercially available anthranils and cyclic amines is described. The developed transformation proceeds with the merits of high step- and atom-efficiency, a broad substrate scope, and good to excellent yields, without additional catalysts, and offers a practical way for the preparation of rutaecarpine and its derivatives with structural diversity.

Synthesis and evaluation of tetrahydroisoquinoline-benzimidazole hybrids as multifunctional agents for the treatment of Alzheimer's disease

A novel series of tetrahydroisoquinoline-benzimidazole hybrids have been designed and synthesized as multifunctional agents against Alzheimer's disease (AD). These compounds were evaluated for their inhibition of neuroinflammation and human β-secretase (hBACE1), and neuroprotective activity. Among them, compound BD3 possessed significant anti-neuroinflammatory activity (IC50 = 5.07 μM against nitric oxide production) through inhibiting the expression and secretion of proinflammatory cytokines in BV2 cells. Compound BD3 also exhibited moderate hBACE1 inhibitory activity (65.7% inhibition at 20 μM) and potent neuroprotective effect by increasing GSH level and reducing ROS production (91.8% cell viability at 5 μM). Parallel artificial membrane permeation assay demonstrated that BD3 could cross the blood-brain barrier (BBB). Thus, this study demonstrates that the compounds with tetrahydroisoquinoline-benzimidazole scaffold are potential anti-AD agents, and they are worth for the further development.