111631-72-2

Usage

Uses

Used in Medicinal Chemistry:
2-(CHLOROACETYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE is used as a compound with potential applications in medicinal chemistry due to its pharmacological activities, such as antifungal and antibacterial properties. Its structure and properties make it a valuable target for research in drug discovery and development.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(CHLOROACETYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE is used as a reagent in chemical reactions, leveraging its unique chemical properties to facilitate the synthesis of other compounds.
Used in Drug Discovery and Development:
2-(CHLOROACETYL)-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE is utilized as a target in drug discovery and development, given its potential to exhibit pharmacological activities that can be harnessed for the creation of new therapeutic agents.

InChI:InChI=1/C13H16ClNO3/c1-17-11-5-9-3-4-15(13(16)7-14)8-10(9)6-12(11)18-2/h5-6H,3-4,7-8H2,1-2H3

Upstream product

• 121580-37-8 [2-(3,4-Dimethoxy-phenyl)-ethyl]-methylene-amine 
• 79-11-8 chloroacetic acid 
• 2328-12-3 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride 
• 79-04-9 chloroacetyl chloride 
• 15365-56-7 6, 7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 50-00-0 formaldehyd 
• 14301-30-5 dichloro-acetic acid-(3,4-dimethoxy-phenethylamide) 

Downstream Products

• 1218949-61-1 2-[4-(2-chloro-6-fluorobenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-ethanone 
• 1218949-62-2 2-[4-(2,4-difluorobenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-ethanone 
• 1218949-49-5 2-(4-benzylpiperazin-1-yl)-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]ethanone 
• 1218949-64-4 1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-2-[4-phenylmethylpiperazin-1-yl]-ethanone 
• 1218949-56-4 1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-2-[4-(4-methylbenzyl)piperazin-1-yl]-ethanone 
• 1218949-55-3 1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-2-[4-(3-methylbenzyl)piperazin-1-yl]-ethanone 
• 1218949-51-9 2-[4-(4-chlorobenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]ethanone 
• 1218949-50-8 2-[(4-bromobenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]ethanone 
• 1218949-59-7 2-[4-(4-t-butylbenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-ethanone 
• 1218949-57-5 1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-2-[4-(4-methoxybenzyl)piperazin-1-yl]-ethanone 
• 1218949-60-0 2-[4-(3,4-dichlorobenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-ethanone 
• 1218949-54-2 1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-2-[4-(4-fluorobenzyl)piperazin-1-yl]-ethanone 
• 1218949-53-1 1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-2-[4-(3-fluorobenzyl)piperazin-1-yl]-ethanone 
• 1218949-63-3 1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-2-[4-(2,4,6-trimethylbenzyl)piperazin-1-yl]-ethanone 

Relevant academic research and scientific papers

Synthesis of σ Receptor Ligands with a Spirocyclic System Connected with a Tetrahydroisoquinoline Moiety via Different Linkers

With the aim to develop new σ2 receptor ligands, spirocyclic piperidines or cyclohexanamines with 2-benzopyran and 2-benzofuran scaffolds were connected to the 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline moiety by variable linkers. In addition to flexible alkyl chains, linkers containing an amide as functional group were synthesized. The 2-benzopyran and 2-benzofuran scaffold of the spirocyclic compounds were synthesized from 2-bromobenzaldehyde. The amide linkers were constructed by acylation of amines with chloroacetyl chloride and subsequent nucleophilic substitution, the alkyl linkers were obtained by LiAlH4 reduction of the corresponding amides. For the development of σ2 receptor ligands, the spirocyclic 2-benzopyran scaffold is more favorable than the ring-contracted 2-benzofuran system. Compounds bearing an alkyl chain as linker generally show higher σ affinity than acyl linkers containing an amide as functional group. A higher σ1 affinity for the cis-configured cyclohexanamines than for the trans-configured derivatives was found. The highest σ2 affinity was observed for cis-configured spiro[[2]benzopyran-1,1′-cyclohexan]-4′-amine connected to the tetrahydroisoquinoline system by an ethylene spacer (cis-31, Ki (σ2)=200 nM; the highest σ1 affinity was recorded for the corresponding 2-benzofuran derivative with a CH2C=O linker (cis-29, Ki (σ1)=129 nM).

Identification of dipeptidyl peptidase IV inhibitors: Virtual screening, synthesis and biological evaluation

Inhibition of dipeptidyl peptidase IV is an important approach for the treatment of type-2 diabetes. In this study, we reported a multistage virtual screening workflow that integrated 3D pharmacophore models, structural consensus docking, and molecular mechanics/generalized Born surface area binding energy calculation to identify novel dipeptidyl peptidase IV inhibitors. After screening our in-house database, two hit compounds, HWL-405 and HWL-892, having persistent high performance in all stages of virtual screening were identified. These two hit compounds together with several analogs were synthesized and evaluated for in vitro inhibition of dipeptidyl peptidase IV. The experimental data indicated that most designed compounds exhibited significant dipeptidyl peptidase IV inhibitory activity. Among them, compounds 35f displayed the greatest potency against dipeptidyl peptidase IV in vitro with the IC 50 value of 78 nm. In an oral glucose tolerance test in normal male Kunming mice, compound 35f reduced blood glucose excursion in a dose-dependent manner. Several compounds with Tetrahydroisoquinoline scaffold were identified by multi-stage virtual screening as the antidiabetic drugs candidates against DPP-4.

Synthesis and biological evaluation of new benzimidazole-thiazolidinedione hybrids as potential cytotoxic and apoptosis inducing agents

A series of new benzimidazole-thiazolidinedione hybrids has been synthesized and evaluated for their cytotoxic potential against a selected human cancer cell lines of prostate (PC-3 and DU-145), breast (MDA-MB-231), lung (A549) and a normal breast epithelial cells (MCF10A). Among the tested compounds, 11p exhibited promising cytotoxicity with IC50value of 11.46?±?1.46?μM on A549 lung cancer cell line and did not show significant toxicity on normal MCF10A cells. Lung cancer cells (A549) have been used to know the mechanism of cell growth inhibition and apoptosis inducing effect with compound 11p. The treatment of A549?cells with 11p showed typical apoptotic morphology like cell shrinkage, chromatin condensation and horseshoe shaped nuclei formation. Flow-cytometry analysis revealed the G2/M phase of cell cycle arrest in a dose dependent manner. Preliminary mechanistic studies suggested that the cell migration was inhibited through the disruption of F-actin protein. Acridine orange-ethidium bromide (AO-EB), DAPI, annexin V-FITC/propidium iodide, rhodamine-123 and MitoSOX assays suggested the induction of apoptosis in A549 cells by compound 11p.

N-substituted isoquinoline derivatives as potential AChE inhibitors

(Chemical Equation Presented) N-substituted donepezil-related isoquinolines have been prepared as potential acetylcholinesterase inhibitors (AChEIs). Microwave assisted procedures and solution-phase parallel synthesis were chosen to optimize the synthetic approach and improve the yields. All synthesized compounds were tested for their AChE inhibitory activity by colorimetric Ellman method and some of them (10, 13, and 28) displayed low inhibitory effects at μM concentrations.

Synthesis and pharmacological evaluation of piperidinoalkanoyl-1,2,3,4- tetrahydroisoquinoline derivatives as novel specific bradycardic agents

A series of piperidinoalkanoyl-1,2,3,4-tetrahydroisoquinoline derivatives were synthesized, and their bradycardic activities were investigated in the isolated right atria of guinea pigs and in conscious rats. These efforts identified the achiral compound 2f, which exhibited potent and long-lasting bradycardic activity with minimal effects on mean blood pressure in conscious rats.

Improved methods for the synthesis of N-acyltetrahydroisoquinolines

One-pot procedures for the synthesis of N-acyltetrahydroisoquinolines have been developed from 2-phenylethylamines, acyl chlorides or carboxylic acids and aldehydes.