22245-98-3

Basic information

• Product Name: 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE
• Synonyms: 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE;6-Hydroxy-3,4-dihydro-1(2H)-isoquinolinone ,97%;6-hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one;1(2H)-Isoquinolinone,3,4-dihydro-6-hydroxy-;3,4-Dihydro-6-hydroxyisoquinolin-1(2H)-one
• CAS NO: 22245-98-3
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.18
• Mol File: 22245-98-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 503.151 °C at 760 mmHg
• Flash Point: 258.097 °C
• Appearance: /
• Density: 1.283 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE(22245-98-3)
• EPA Substance Registry System: 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE(22245-98-3)

Safety Data

• Hazardous Substances Data: 22245-98-3(Hazardous Substances Data)

Usage

General Description

6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE is a chemical compound with the molecular formula C9H9NO2. It is a derivative of isoquinolinone and is found in the roots of plants from the family Papaveraceae. 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE has been studied for its potential pharmacological properties, including its ability to act as an antioxidant and anti-inflammatory agent. It has also been investigated for its potential in treating neurological disorders and as a therapeutic agent for cardiovascular diseases. Additionally, 6-HYDROXY-3,4-DIHYDRO-1(2H)-ISOQUINOLINONE may have potential applications in the design and development of new pharmaceutical drugs. Further research is needed to fully understand the effects and potential uses of this compound.

InChI:InChI=1/C9H9NO2/c11-7-1-2-8-6(5-7)3-4-10-9(8)12/h1-2,5,11H,3-4H2,(H,10,12)

Upstream product

• 22246-12-4 6-methoxy-1,2,3,4-tetrahydro-1-oxoisoquinoline 
• 3470-49-3 5-hydroxy-2,3-dihydro-1H-indene-1-one 
• 33543-63-4 ethyl-N-<2-(3-methoxyphenyl)ethyl>-carbamate 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 5111-70-6 5-methoxy-1-indanone 
• 76-03-9 trichloroacetic acid 
• 110192-21-7 N-(methoxycarbonyl)-2-(3'-methoxyphenyl)ethylamine 
• 588-05-6 m-tyramine 

Downstream Products

• 164147-66-4 6-(benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one 
• 164147-67-5 (6-Benzyloxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester 
• 190604-20-7 6-[(4-cyanophenyl)-(E)-ethenyl]-3,4-dihydro-1-oxo-2(1H)-isoquinolineacetic acid 1,1-dimethylethyl ester 
• 164147-72-2 [6-(4-Cyano-phenylethynyl)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 1027969-04-5 [6-(3-Aminomethyl-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 164147-69-7 [6-(4-Cyano-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 164148-48-5 [6-(4-Aminomethyl-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 190604-17-2 {6-[2-(4-Cyano-phenyl)-ethoxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester 
• 1027422-55-4 {1-Oxo-6-[(E)-2-(4-thiocarbamoyl-phenyl)-vinyl]-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester 
• 1026228-40-9 {6-[(E)-2-(4-Carbamimidoyl-phenyl)-vinyl]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester 
• 164147-78-8 (6-Benzyloxycarbonylamino-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester 
• 164147-70-0 [6-(4-Carbamimidoyl-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 164147-80-2 [6-(4-Cyano-benzoylamino)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 1026339-13-8 [1-Oxo-6-(4-thiocarbamoyl-phenylethynyl)-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 

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.

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.

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.