25263-48-3

Upstream product

• 100-52-7 benzaldehyde 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 19712-49-3 6-methoxy-1-phenyl-3,4-dihydroisoquinoline 
• 3278-19-1 N-[2-(4-methoxyphenyl)ethyl]benzamide 
• 110339-54-3 N-[2-(3-methoxy-phenyl)-ethyl]-formamide 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 19712-48-2 N-benzoyl-2-(3-methoxyphenyl)ethylamine 

Downstream Products

• 19712-47-1 6-methoxy-2-methyl-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 347979-00-4 2,2,2-Trifluoro-1-(6-methoxy-1-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)ethanone 
• 347979-10-6 2,2,2-Trifluoro-1-(6-hydroxy-1-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)ethanone 
• 19712-46-0 N-methyl-6-hydroxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 1349743-77-6 (R,S)-6-methoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-sulfonamide 

Relevant academic research and scientific papers

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.

Synthesis and biological profile of new 1,2,3,4-tetrahydroisoquinolines as selective carbonic anhydrase inhibitors

In a previous paper we identified several 1-aryl-6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline-2-sulfonamides that displayed inhibitory effects toward selected carbonic anhydrase isozymes at micromolar concentration. In order to deepen the structure-activ

Strategies and synthetic methods directed toward the preparation of libraries of substituted isoquinolines

Strategies for the production of substituted isoquinoline libraries were developed and explored. Routes involving microwave-assisted variants of the Bischler-Napieralski or Pictet-Spengler reaction allowed for cyclization of substituted β-arylethylamine derivatives. The dihydroisoquinolines and tetrahydroisoquinolines thus generated could then be oxidized to their corresponding isoquinoline analogues. An alternate strategy, however, involving the preparation and activation of isoquinolin-1(2H)-ones is demonstrated to be a more practical, rapid, and efficient route to C1- and C4-substituted isoquinoline libraries.

O-Benzenedisulfonimide as a reusable acid catalyst for an easy, efficient, and green synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines through Pictet-Spengler reaction

The synthesis of tetrahydroisoquinolines and tetrahydro-β-carbolines, using the Pictet-Spengler reaction, was carried out in the presence of a catalytic amount of o-benzenedisulfonimide, which worked as a Br?nsted acid organocatalyst. The reaction conditi

3D pharmacophore models for 1,2,3,4-tetrahydroisoquinoline derivatives acting as anticonvulsant agents

A 3D pharmacophore model predicting anticonvulsant activity was obtained for a series of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives recently disclosed as a new class of non-competitive AMPA receptor antagonists. The training set included 17

Tetrahydroisoquinolines as subtype selective estrogen agonists/antagonists

Two series of 6-hydroxy and 7-hydroxy tetrahydroisoquinolines were prepared. Evaluating a range of C-1, C-4, and N-substituents led to the discovery of ER α and ER β selective analogs.

Tetrahydroisoquinoline compounds as estrogen agonists/antagonists

This invention relates to compounds useful for treating or preventing obesity, breast cancer, osteoporosis, endometriosis, cardiovascular disease, prostatic disease, and the like, and to pharmaceutical composition, methods, and kits comprising such compou

Abnormal products in the Bischler-Napieralski isoquinoline synthesis

Reaction of N-[2-(4-methoxyphenyl)ethyl]benzamides with phosphorus pentoxide (and phosphoryl chloride) gives 7-methoxy-1-phenyl-3,4-dihydroisoquinolines (a normal Bischler-Napieralski reaction product) and 6-methoxy-1-phenyl-3,4-dihydroisoquinolines (an abnormal reaction product). The reaction mechanism is discussed.

Synthesis and Molecular Modeling of 1-Phenyl-1,2,3,4-tetrahydroisoquinolines and Related 5,6,8,9-Tetrahydro-13bH-dibenzoquinolizines as D1 Dopamine Antagonists

New 1-phenyl-1,2,3,4-tetrahydroisoquinolines and related 5,6,8,9-tetrahydro-13bH-dibenzo-quinolizines were prepared as ring-contracted analogs of the prototypical 1-phenyl-2,3,4,5-tetrahydrobenzazepines (e.g., SCH23390) as a continuation of our studi