55507-15-8

Basic information

• Product Name: 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 55507-15-8
• Molecular Formula: C₁₇H₁₈ClNO₂
• Molecular Weight: 303.78
• Mol File: 55507-15-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(55507-15-8)
• EPA Substance Registry System: 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(55507-15-8)

Safety Data

• Hazardous Substances Data: 55507-15-8(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry Research:
1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline is used as a research compound for exploring its potential pharmacological properties. Its unique molecular structure and substitution pattern make it a promising candidate for studying the structure-activity relationships of tetrahydroisoquinoline derivatives, which can contribute to the development of new drugs and therapeutic agents.
Used in Drug Discovery and Development:
In the pharmaceutical industry, 1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline is used as a lead compound for the development of potential therapeutic agents. Its specific chemical properties and biological activities are of interest for targeting various medical conditions, making it a valuable molecule in the search for novel treatments and cures.
Used in Structure-Activity Relationship Studies:
1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline is utilized as a key molecule in structure-activity relationship studies. These studies aim to understand how the specific molecular structure of the compound influences its biological activity, which can guide the design and synthesis of more effective and selective drugs.

Upstream product

• 5467-91-4 1,3-bis[2-(3,4-dimethoxyphenyl)ethyl]urea 
• 104-88-1 4-chlorobenzaldehyde 
• 15994-13-5 N-(4-chlorobenzylidene)-2-(3,4-dimethoxyphenyl)ethanamine 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 910108-64-4 2-(chloroacetyl)-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1161432-36-5 (R,S)-1-(4'-chlorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamide 
• 76201-90-6 6,7-dimethoxy-1-<(para-chloro)phenyl>-3,4-dihydroisoquinoline 
• 75448-45-2 1-(4-chlorophenyl)-6,7-dimethoxyisoquinoline 
• 1448701-62-9 (-)-1-(4-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1147279-87-5 N-tert-butyl-1-(4-chlorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1147279-71-7 1-(4-chlorophenyl)-N-isopropyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-carboxamide 
• 1147279-80-8 N-butyl-1-(4-chlorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxamide 
• 1147279-54-6 1-(4-chlorophenyl)-N-ethyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-carboxamide 
• 1147279-95-5 1-(4-chlorophenyl)-N-cyclopentyl-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-carboxamide 
• 1019906-98-9 ethyl 2-[1-(4-chlorophenyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl]-2-oxoacetate 
• 879290-26-3 10b-(4-chlorophenyl)-8,9-dimethoxy-6,10b-dihydro-5H-isoxazolo[3,2-a]isoquinoline-1,2-dicarboxylic acid dimethyl ester 
• 861221-63-8 N-acetyl-1-(4'-chlorophenyl)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 886035-16-1 N-acetyl-1-(4'-chlorophenyl)-6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Synthesis, resolution, stereochemistry, and molecular modeling of (R)- and (S)-2-acetyl-1-(4′-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline AMPAR antagonists

Recently we identified (R,S)-2-acetyl-1-(4′-chlorophenyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (6) as a potent non-competitive AMPA receptor antagonist able to prevent epileptic seizures. We report here the optimized synthesis of compound 6, its r

Tetrahydroisoquinoline-Derived Urea and 2,5-Diketopiperazine Derivatives as Selective Antagonists of the Transient Receptor Potential Melastatin 8 (TRPM8) Channel Receptor and Antiprostate Cancer Agents

Tetrahydroisoquinoline derivatives containing embedded urea functions were identified as selective TRPM8 channel receptor antagonists. Structure-activity relationships were investigated, with the following conclusions: (a) The urea function and the tetrahydroisoquinoline system are necessary for activity. (b) Bis(1-aryl-6,7dimethoxy-1,2,3,4-tetrahydroisoquinolyl)ureas are more active than compounds containing one tetrahydroisoquinoline ring and than an open phenetylamine ureide. (c) Trans compounds are more active than their cis isomers. (d) Aryl substituents are better than alkyls at the isoquinoline C-1 position. (e) Electron-withdrawing substituents lead to higher activities. The most potent compound is the 4-F derivative, with IC50 in the 10-8 M range and selectivities around 1000:1 for most other TRP receptors. Selected compounds were found to be active in reducing the growth of LNCaP prostate cancer cells. TRPM8 inhibition reduces proliferation in the tumor cells tested but not in nontumor prostate cells, suggesting that the activity against prostate cancer is linked to TRPM8 inhibition.

Probing Molecular Interactions between Human Carbonic Anhydrases (hCAs) and a Novel Class of Benzenesulfonamides

On the basis of X-ray crystallographic studies of the complex of hCA II with 4-(3,4-dihydro-1H-isoquinoline-2-carbonyl)benzenesulfonamide (3) (PDB code 4Z1J), a novel series of 4-(1-aryl-3,4-dihydro-1H-isoquinolin-2-carbonyl)benzenesulfonamides (23-33) wa

In Vivo Evaluation of Selective Carbonic Anhydrase Inhibitors as Potential Anticonvulsant Agents

Epilepsy is a common neurological disorder caused by an imbalance between inhibitory and excitatory neurotransmission. It is well known that neuronal excitability is related to γ-aminobutyric acid (GABA)ergic depolarization. HCO3?-dependent depolarization can be suppressed by membrane-permeable inhibitors of carbonic anhydrase. We previously identified some isoquinoline sulfonamides as potent and selective inhibitors of the human carbonic anhydrase II and VII (hCA II and hCA VII) isoforms. Given that hCA II and hCA VII are specific isoforms involved in GABA-mediated neuronal excitation, we hypothesized that they could represent the biological target for the development of new anticonvulsant agents. Therefore, for selected isoquinoline sulfonamides, we preliminarily tested their ability to prevent audiogenic seizures in DBA/2 mice. All compounds were evaluated after intraperitoneal administration, and some of them proved to protect the mice against convulsions. Among this series of compounds, several derivatives showed combined in vivo efficacy with inhibitory effects toward the targeted carbonic anhydrases (i.e., hCA II and hCA VII). Specifically, the most interesting molecule was 1-(4-aminophenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamide (6), which proved to be a more active and selective hCA VII inhibitor than the reference compound topiramate. Further studies to explore the in vivo pharmacokinetic profile of the most active compounds may help to provide insight into the future design of selective hCA VII inhibitors.

Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst

Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts.

Synthesis and evaluation of pharmacological profile of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides

In previous studies we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives displaying potent anticonvulsant effects in different animal models of epilepsy. With the aim to deepen the structure-activity relationships (SAR) fo

Synthesis of carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7- dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as new potential PET AMPA receptor ligands

New carbon-11 and fluorine-18 labeled N-acetyl-1-aryl-6,7-dimethoxy-1,2,3, 4-tetrahydroisoquinoline derivatives were designed and synthesized as potential positron emission tomography AMPA (2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic acid) recep

Synthesis, antibacterial activity and QSAR studies of 1,2-disubstituted-6, 7-dimethoxy-1,2,3,4-tetrahydroisoquinolines

Some new substituted-tetrahydroisoquinoline derivatives were synthesized and evaluated for their in vitro antimicrobial activities against the standard Gram positive and Gram negative strains: Staphylococcus aureus (ATCC 25923), S.:epidermidis (WHO-6), Es

Synthesis and anticonvulsant properties of tetrahydroisoquinoline derivatives

As a follow up of our previous structure-activity relationship and molecular modeling studies, we synthesized a novel series of 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as potential non-competitive AMPA receptor antagonists. When te

Discovery of a novel and highly potent noncompetitive AMPA receptor antagonist

N-Acetyl-1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives were designed and synthesized as potential noncompetitive AMPA receptor antagonists on the basis of molecular modeling studies. Sound-induced seizure testing showed that this class o