22246-04-4

Basic information

• Product Name: 7-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE
• Synonyms: 7-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE;1(2H)-Isoquinolinone, 3,4-dihydro-7-Methoxy-;7-methoxy-1,2,3,4-tetrahydroisoquinolin-1-one;7-methoxy-3,4-dihydroisoquinolin-1-ol;7-methoxy-3,4-dihydroisoquinolin-1-one
• CAS NO: 22246-04-4
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• EINECS: 200-258-5
• Mol File: 22246-04-4.mol
• Article Data: 36

Chemical Properties

• Melting Point: 112-114 °C(Solv: chloroform (67-66-3); ethyl ether (60-29-7))
• Boiling Point: 435.789 °C at 760 mmHg
• Flash Point: 217.358 °C
• Appearance: /
• Density: 1.16 g/cm³
• 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: 7-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(22246-04-4)
• EPA Substance Registry System: 7-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE(22246-04-4)

Safety Data

• Hazardous Substances Data: 22246-04-4(Hazardous Substances Data)

Usage

General Description

7-METHOXY-3,4-DIHYDRO-2H-ISOQUINOLIN-1-ONE is a chemical compound that belongs to the isoquinolinone class. It is a derivative of isoquinolinone, a heterocyclic compound that contains a benzene ring fused to a nitrogen-containing pyridine ring. This particular compound has a methoxy group attached to the 7th carbon atom of the isoquinolinone ring, and a dihydro group at the 3rd and 4th carbon atoms. It has potential biological and pharmacological activities, and its structure may be of interest for medicinal chemistry and drug discovery. It is important to note that the compound may have various properties and uses depending on its specific context and application.

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

Upstream product

• 16027-16-0 7-methoxy-2H-isoquinolin-1-one 
• 91247-71-1 2-4-methoxyphenylethylcarbamic acid methyl ester 
• 136390-01-7 ethyl-N-<2-(4-methoxyphenyl)ethyl>-carbamate 
• 4697-58-9 2,9,10-trimethoxy-berbine 
• 55-81-2 4-Methoxyphenethylamine 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 
• 101033-24-3 4-methoxycinnamyl isocyanate 
• 13623-25-1 6-methoxy-2,3-dihydro-1H-inden-1-one 
• 33543-63-4 ethyl-N-<2-(3-methoxyphenyl)ethyl>-carbamate 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 541-41-3 chloroformic acid ethyl ester 
• 1616291-03-2 8-chloro-7-methoxyisoquinolin-1(2H)-one 
• 86269-98-9 2-chloro-3-methoxybenzoyl chloride 

Downstream Products

• 22246-05-5 7-hydroxy-3,4-dihydro-1-oxo-2(1H)-isoquinoline 
• 190604-11-6 7-(benzyloxy)-3,4-dihydroisoquinolin-1(2H)-one 
• 190604-12-7 (7-Benzyloxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester 
• 190604-14-9 [7-(4-Cyano-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 1027994-02-0 {6-[2-(4-Carbamimidoyl-phenyl)-ethoxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester 
• 1026177-04-7 [1-Oxo-7-(4-thiocarbamoyl-benzyloxy)-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 1027514-28-8 [7-(4-Carbamimidoyl-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 1026846-42-3 [7-(4-Methylsulfanylcarbonimidoyl-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid tert-butyl ester 
• 190604-15-0 {7-[4-(tert-Butoxycarbonylamino-imino-methyl)-benzyloxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid tert-butyl ester 
• 1354030-55-9 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-3,4-dihydroisoquinolin-1(2H)-one 
• 1354030-67-3 7-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propoxy)-3,4-dihydroisoquinolin-1(2H)-one 
• 1354030-69-5 7-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-3,4-dihydroisoquinolin-1(2H)-one 
• 1354030-23-1 7-(3-(4-(2,3-dichlorophenyl)-1,4-diazepan-1-yl)propoxy)-3,4-dihydroisoquinolin-1(2H)-one 
• 1354030-25-3 UNC₉₉₇₅ 

Relevant articles and documents

Synthesis, in vitro cytotoxicity, and molecular docking study of novel 3,4-dihydroisoquinolin-1(2H)-one based piperlongumine analogues

With the aim of expanding the scope of SAR on piperlongumine (PL), a naturally occurring anticancer molecule, we have designed a novel hybrid molecule bearing 3,4-dihydroisoquinolin-1(2H)-one and trans-cinnamic acids. The structure, based on hybridization strategy, is used for hybridization of naturally occurring scaffolds. We have synthesized 14 hybrid molecules by coupling 3,4-dihydroisoquinolin-1(2H)-one core with cinnamic acids using the mix anhydride approach. The newly synthesized inhibitors were evaluated for cell viability against breast cancer MCF-7 and cervical cancer HeLa cell lines. Furthermore, the active compounds were screened for their potential in breast cancer MDA-MB-231, cervical cancer C33A cell lines, prostate cancer DU-145, PC-3, and normal VERO cells. From the series, compound 10g was seen to inhibit MCF-7 cell growth significantly with GI50 50 = 20 μM) and C33A (GI50 = 3.2 μM). While the inhibitor 10i inhibits MCF-7 breast cancer cell growth GI50 = 3.42 μM along with inhibition of cell growth in MDA-MB-231 (GI50 = 30 μM), HeLa (GI50 = 7.67 μM), C33A (GI50 = 13 μM), DU-145 (GI50 = 6.45 μM), PC-3 (GI50 = 8.68 μM), and VERO (GI50 = 2.93 μM), respectively. Furthermore, molecular docking study demonstrated these compounds could bind tightly to the colchicine domain of tubulin through a network of favorable steric and electrostatic interactions and thus act as a tubulin polymerization inhibitor.

Preparation method of amide-like derivative and intermediate thereof

The invention discloses a preparation method of an amide-like derivative and an intermediate thereof. The invention provides a preparation method of a compound as shown in a formula VI and an intermediate thereof, the compound as shown in the formula VI c

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.