55841-58-2

Usage

Chemical family

Isoquinolinium family It belongs to a group of organic compounds derived from isoquinoline.

Type of compound

Quaternary ammonium compound It contains a central nitrogen atom bonded to four organic groups.

Ions present

Contains a bromide ion The compound has a positively charged nitrogen atom and a negatively charged bromide ion, making it a salt.

Functional groups

Methoxy group and oxoethyl group These groups are attached to the isoquinolinium core, contributing to the compound's reactivity and properties.

Usage

Reactant in organic synthesis It is used as a building block for the synthesis of more complex organic molecules.

Pharmaceutical intermediate

Used in the synthesis of pharmaceuticals It serves as a precursor to various drugs and drug candidates.

Medicinal applications

Studied for potential use in medicine The compound has been investigated for its potential therapeutic effects.

Antitumor activity

Investigated for potential anti-cancer properties It has been studied for its ability to inhibit the growth of cancer cells.

Antifungal activity

Investigated for potential antifungal properties It has been studied for its ability to inhibit the growth of fungi.

Structure and properties

Suitable for a wide range of chemical reactions The compound's structure allows it to participate in various types of chemical reactions, making it a versatile building block in organic chemistry.

Upstream product

• 119-65-3 isoquinoline 
• 96-32-2 bromoacetic acid methyl ester 
• 698396-17-7 (1H-isoquinolin-2-yl)-acetic acid methyl ester 

Downstream Products

• 113305-92-3 1-methoxycarbonyl-2-methylthio-1-(1-isoquinolinio)-2-(N-p-toluenesulfonylimino)ethylide 
• 113305-93-4 methyl 2-methylthioimidazo<2,1-a>isoquinoline-3-carboxylate 
• 142011-54-9 methyl 1-cyano-2-(p-toluenesulfonylamino)pyrrolo<2,1-a>isoquinoline-3-carboxylate 
• 142011-51-6 dimethyl 2-(p-toluenesulfonylamino)pyrrolo<2,1-a>isoquinoline-1,3-dicarboxylate 
• 109833-20-7 C₁₅H₂₄N₄O₁₀ 
• 130090-72-1 triethyl 2-[(1E)-N-(ethoxycarbonyl)-2-oxo-2-phenylethanehydrazonoyl]hydrazine-1,1,2-tricarboxylate 
• 698396-17-7 (1H-isoquinolin-2-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and photophysical insights of new fused N-heterocyclic derivatives with isoquinoline skeleton

Six new fused isoquinoline based compounds (compounds 5a–c with pyrrolo[2,1-a] isoquinoline structure and compounds 6a–c with imidazo[2,1-a]isoquinoline skeleton) have been synthesized using the [3 + 2] cycloaddition of the several in situ generated cycloimmonium ylides to ethyl propiolate or ethyl cyanoformate. All the synthesized compounds have been investigated in solution by UV–VIS absorption, steady and time-resolved fluorescence methods. The effect of the substituents on the spectral characteristics has been demonstrated. These derivatives displayed an intense emission between 360 and 420 nm. The emission quantum yields (Φ = 0.54–0.64) of pyrroloisoquinoline derivatives in dimethylsulfoxide (DMSO) were significantly higher than those of imidazoquinolines (0.03–0.16). The fluorescence decay of isoquinoline derivatives follows a biexponential law. A noticeable response of these isoquinoline derivatives to sodium hydroxide was observed.

External oxidant-free oxidation/[3+2] cycloaddition/aromatization cascade: Electrochemical synthesis of polycyclic N-heterocycles

Here, we describe an efficient and environmentally friendly synthesis of polycyclic N-heterocycles under electrochemical external oxidant-free conditions. The extent of the sequential electrochemical oxidative aromatization can be regulated with the assistance of redox mediators.

Synthesis of 2-aminoindolizines by 1,3-dipolar cycloaddition of pyridinium ylides with electron-deficient ynamides

Electron-deficient ynamides, possessing an ynoate or an ynone moiety, have been successfully involved for the first time in a 1,3-dipolar cycloaddition with stabilized pyridinium ylides. These reactions afford an efficient and general access toward a variety of substituted 2-aminoindolizines which can serve as useful precursors for the synthesis of other more complex nitrogen heterocycles.

1,2-Dihydroisoquinoline-N-Acetic Acid Derivatives as New Carriers for Specific Brain Delivery I: Synthesis and Estimation of Oxidation Kinetics Using Multivariate Calibration Method

In order to overcome the slow oxidation of 1,2-dihydro-N-alkylisoquinoline, 1,2-dihydroisoquinoline-N-acetic acid derivatives (3 b-d) were designed and synthesized as new chemical delivery systems (CDS) for the brain. Molecular orbital calculations for th

Preparation of 1-trifluoroacetyl indolizines and their derivatives via the cycloaddition of pyridinium N-ylides with 4-4-ethoxy1-1,1,1-trifluorobut-3-en-one

Under basic reaction conditions pyridinium or isoquinolinium N-ylides (C5H5N+ CH2YBr- or C9H7N+CH2YBr-, Y : CO2R, CN, PhCO) reacted readily with 4-ethoxyl-1,1,1-trifluorobut-3-en-2-one to give the corresponding 1-trifluoroacetyl substituted indolizines or pyrrolo-[1,2-a]isoquinolines. The molecular structure of 1-trifluoromethyl-3-methoxyl-pyrrolo-[1,2-a]isoquinoline is presented.

Stereoselective Cycloaddition of Pyridinium or Isoquinolinium Methylides with Olefinic Dipolarophiles and Subsequent Cycloadditions of the Cycloadducts with Nitrile Oxides

Pyridinium or isoquinolinium methylides undergo highly stereo- and regioselective cycloadditions with olefinic dipolarophiles to form unstable tetrahydroindolizine derivatives.One of the two double bonds existing in the dihydro heteroaromatic ring of the cycloadducts reacts with nitrile oxides, in the same flask, in stereo-, regio-, and periselective fashions to lead to stable isoxazole-fused tetrahydroindolizines in good yields.