22246-12-4

Basic information

• Product Name: 6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• Synonyms: 6-METHOXY-3,4-DIHYDROISOQUINOLIN-1(2H)-ONE;6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE;6-METHOXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE;6-METHOXY-3,4-1(1H)-ISOQUINOLINONE;6-Methyl-3,4-dihydroisoquinolin-1(2H)-one;1(2H)-Isoquinolinone, 3,4-dihydro-6-methoxy-;6-(Methyloxy)-3,4-dihydro-1(2H)-isoquinolinone;6-Methoxy-1,2,3,4-tetrahydroisoquinolin-1-one
• CAS NO: 22246-12-4
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: 1308068-626-2
• Product Categories: Quinoline series
• Mol File: 22246-12-4.mol
• Article Data: 49

Chemical Properties

• Melting Point: 136-138℃
• Boiling Point: 439.787 °C at 760 mmHg
• Flash Point: 219.775 °C
• Appearance: /
• Density: 1.159
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.77±0.20(Predicted)
• CAS DataBase Reference: 6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(22246-12-4)
• EPA Substance Registry System: 6-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(22246-12-4)

Safety Data

• Hazardous Substances Data: 22246-12-4(Hazardous Substances Data)

Usage

General Description

6-Methoxy-3,4-dihydro-2H-isoquinolin-1-one is a chemical compound generally recognized for its role in chemical research and experimentations. It is a derivative of Isoquinoline, an organic compound and a heterocyclic aromatic alkaloid. Owing to its complex structure and properties, it is often utilized in organic chemistry for creating numerous pharmacological substances. However, specific biological activities, safety, and efficacy of 6-Methoxy-3,4-dihydro-2H-isoquinolin-1-one are not comprehensively studied and acknowledged yet, thus handling the compound requires professional skill and care.

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

• 5111-70-6 5-methoxy-1-indanone 
• 75-09-2 dichloromethane 
• 74-85-1 ethene 
• 1293990-75-6 N-tert-pentanoyloxy-p-methoxybenzamide 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 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 
• 40478-49-7 3-(3-methoxyphenyl)propanoyl chloride 
• 10516-71-9 3-(3-Methoxy-phenyl)-propionic acid 
• 62334-10-5 1-isocyano-2-(3-methoxyphenyl)ethane 
• 33543-63-4 ethyl-N-<2-(3-methoxyphenyl)ethyl>-carbamate 
• 163713-49-3 3-(3-Methoxy-phenyl)-propionyl azide 

Downstream Products

• 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 
• 844431-68-1 2-(4-fluoro-phenyl)-6-methoxy-1-(4-pyridin-4-yl-phenyl)-1,2,3,4-tetrahydro-isoquinoline 
• 844431-69-2 2-(3-fluorophenyl)-6-methoxy-1-[4-pyridin-4-ylphenyl]-1,2,3,4-tetrahydroisoquinoline 
• 844431-70-5 6-methoxy-2-(3-methoxy-phenyl)-1-(4-pyridin-4-yl-phenyl)-1,2,3,4-tetrahydro-isoquinoline 
• 844431-48-7 6-methoxy-2-(3-methoxyphenyl)-1-[4-(4-methylpiperazin-1-yl)phenyl]-1,2,3,4-tetrahydroisoquinoline 
• 938156-14-0 6-methoxy-2-(3-methoxy-phenyl)-1-[4-(1-methyl-piperidin-4-yl)-phenyl]-1,2,3,4-tetrahydro-isoquinoline 
• 938156-10-6 2-(3-fluoro-phenyl)-6-methoxy-1-[4-(1-methyl-piperidin-4-yl)-phenyl]-1,2,3,4-tetrahydro-isoquinoline 
• 938155-47-6 2-(4-fluoro-phenyl)-6-methoxy-1-[4-(1-methyl-piperidin-4-yl)-phenyl]-1,2,3,4-tetrahydro-isoquinoline 
• 844431-49-8 1-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-6-methoxy-2-(3-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinoline 
• 844431-50-1 1-[4-(4-isobutyl-piperazin-1-yl)-phenyl]-6-methoxy-2-(3-methoxy-phenyl)-1,2,3,4-tetrahydro-isoquinoline 

Relevant articles and documents

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.

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.

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.