780004-18-4

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLATE is used as a building block for the synthesis of various pharmaceutical compounds due to its diverse pharmacological activities and potential therapeutic applications.
Used in Neurodegenerative Disease Treatment:
In the field of neurology, ETHYL 6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLATE is used as a potential candidate for the treatment of neurodegenerative diseases, leveraging its pharmacological properties to address these conditions.
Used in Antioxidant Formulations:
ETHYL 6-HYDROXY-1,2,3,4-TETRAHYDRO-ISOQUINOLINE-1-CARBOXYLATE is utilized as an antioxidant in formulations to combat oxidative stress, which is implicated in various pathological conditions.
Used in Anti-inflammatory and Analgesic Applications:
It is also considered in anti-inflammatory and analgesic applications due to its potential to reduce inflammation and alleviate pain, making it a candidate for treatments in these areas.

InChI:InChI=1/C12H15NO3/c1-2-16-12(15)11-10-4-3-9(14)7-8(10)5-6-13-11/h3-4,7,11,13-14H,2,5-6H2,1H3

Upstream product

• 125068-10-2 3 
• 125068-05-5 N-[2-(3-methoxyphenyl)-ethyl]oxalamic acid ethyl ester 
• 2039-67-0 2-(3-methoxyphenyl)-1-ethanamine 
• 64-17-5 ethanol 
• 38449-59-1 2-(3-hydroxyphenyl)ethylamine hydrobromide 
• 91523-50-1 rac-6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid 

Relevant academic research and scientific papers

Efficient dynamic kinetic resolution method for the synthesis of enantiopure 6-hydroxy- and 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Enantiomeric 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), useful in the synthesis of modulators of nuclear receptors, including liver X receptor and its analogue 6-methoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (ee >99%), a source of the above enantiomer was synthesized through Candida antarctica lipase B-catalysed dynamic kinetic hydrolysis of the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic esters (±)-4·HCl and (±)-5. (R)-Selective hydrolysis in both organic solvents and an aqueous NH4OAc buffer at pH 8.5 was observed and the amino acids were obtained in good chemical yields (>87%).

6-Substituted decahydroisoquinoline-3-carboxylic acids as potent and selective conformationally constrained NMDA receptor antagonists

We have prepared a series of 6-substituted decahydroisoquinoline-3- carboxylic acids, and structurally similar analogs, as potential N-methyl-D- aspartate receptor antagonists. There is a large body of evidence to support the use of such compounds as cerebroprotective agents in a variety of acute and chronic neurodegenerative disorders, where some component of glutamate- mediated excitotoxicity may exist. The compounds prepared were evaluated in vitro in both receptor binding assays ([3H]CGS19755, [3H]AMPA, and [3H]kainic acid) and in a cortical wedge preparation (versus NMDA, AMPA, and kainic acid) to determine affinity, potency, and selectivity. The new amino acids were also evaluated in vivo for their ability to block NMDA-induced lethality in mice. We synthesized many of the possible diastereomers of the decahydroisoquinoline nucleus in order to examine the spatial and steric requirements for affinity at the NMDA receptor and activity as NMDA antagonists. From our structure-activity relationship we identified two potent and selective NMDA receptor antagonists, the phosphonate- and tetrazole-substituted amino acids 31a and 32a, respectively, that show good activity in animals following systemic administration. For example, 31a and 32a selectively displaced [3H]CGS19755 binding with IC50s of 55 ± 14 and 856 ± 136 nM, respectively, and selectively antagonized responses due to NMDA in a cortical wedge preparation with IC50s of 0.15 ± 0.01 and 1.39 ± 0.29 μM, respectively. And compounds 31a and 32a blocked NMDA-induced lethality in mice with minimum effective doses of 1.25 and 2.5 mg/kg (intraperitoneal), respectively. These novel amino acids are among some of the most potent NMDA antagonists described thus far, and are excellent candidates for development as neuroprotective agents for a number of CNS disorders.