871224-64-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-((R)-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide is used as a pharmaceutical agent for the treatment of various disorders. Its specific molecular structure allows it to interact with biological targets, such as receptors or enzymes, to modulate their activity and produce therapeutic effects.
Used in Medicinal Chemistry Research:
(R)-2-((R)-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide is also used in medicinal chemistry research to study the structure-activity relationships of isoquinoline derivatives. By synthesizing and testing various analogs, researchers can gain insights into the molecular features that contribute to their biological activity and optimize their potency and selectivity for specific therapeutic applications.
Used in Drug Discovery:
(R)-2-((R)-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinolin-2(1H)-yl)-N-methyl-2-phenylacetamide serves as a starting point for drug discovery efforts. Its unique structure and potential biological activity make it a promising candidate for the development of new drugs targeting various diseases and conditions.

Biological Activity

almorexant is an antagonist of orexin 1 receptor (ox1r) and orexin 2 receptor (ox2r) with kd values of 1.3nm and 0.17nm, respectively [1].almorexant is a dual ox antagonist. it inhibits the binding of orexin-a to both ox1r and ox2r with ic50 values of 6.6nm and 3.4nm, respectively. in the inositol phosphates assay, almorexant acts as a competitive antagonist of hox1r but a noncompetitive-like antagonist of hox2r. besides that, almorexant is found to block the increase in locomotor activity induced by icv orexin in c57bl/6 mice. furthermore, almorexant shows effects on sleep in multiple species, including man. it reduces the time spent awake and increased the time spent in nrem and rem sleep dose-dependently in normal c57bl/6 mice. these effects on sleep caused by almorexant are mediated by ox2rs as almorexant has no effect in mice lacking both ox1r and ox2r but has effects in mice lacking only ox1r [1, 2].

references

[1] malherbe p, borroni e, pinard e, wettstein jg, knoflach f. biochemical and electrophysiological characterization of almorexant, a dual orexin 1 receptor (ox1)/orexin 2 receptor (ox2) antagonist: comparison with selective ox1 and ox2 antagonists. mol pharmacol. 2009 sep;76(3):618-31.[2] mang gm1, dürst t, bürki h, imobersteg s, abramowski d, schuepbach e, hoyer d, fendt m, gee ce. the dual orexin receptor antagonist almorexant induces sleep and decreases orexin-induced locomotion by blocking orexin 2 receptors. sleep. 2012 dec 1;35(12):1625-35.

Upstream product

• 132283-68-2 2-(2-chloroethyl)-4,5-dimethoxybenzaldehyde 
• 1609564-22-8 (S)-tert-butyl-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 1609564-20-6 (S)-tert-butyl 1-(2-hydroxy-2-(4-(trifluoromethyl)phenyl)ethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 884337-44-4 (S)-1-allyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 
• 181220-97-3 (S)-1-allyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1415385-75-9 (S)-1-allyl-2-((R)-tert-butylsulfinyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 1415385-74-8 (R)-N-((S)-1-(2-(2-chloroethyl)-4,5-dimethoxyphenyl)but-3-enyl)-2-methylpropane-2-sulfinamide 
• 769172-81-8 (S)-6,7-dimethoxy-1-(4-(trifluoromethyl)phenethyl)-1,2,3,4-tetrahydroisoquinoline 
• 871224-68-9 (S)-2-(methylamino)-2-oxo-1-phenylethyl 4-methylbenzenesulfonate 
• 51685-62-2 N-methyl-2-bromo-2-phenylethanamide 
• 871224-77-0 {(1S)-6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-3,4-dihydro-1H-isoquinolin-2-yl}-phenyl-acetic acid 
• 593-51-1 methylamine hydrochloride 
• 324076-69-9 6,7-dimethoxy-1-[2-(4-trifluoromethyl-phenyl)-ethyl]-3,4-dihydroiso-quinoline 

Downstream Products

• 913358-93-7 almorexant hydrochloride 

Relevant academic research and scientific papers

Stereoselective total synthesis of almorexant

A highly stereoselective synthesis of almorexant has been achieved using (R)-tert-butanesulfinamide as a chiral source. The chiral tetrahydroisoquinoline core was constructed through allylation of chiral N-sulfinyl imine followed by ring closure of the se

Enantioselective synthesis of almorexant via iridium-catalysed intramolecular allylic amidation

An enantioselective synthesis of almorexant, a potent antagonist of human orexin receptors, is presented. The chiral tetrahydroisoquinoline core structure was prepared via iridium-catalysed asymmetric intramolecular allylic amidation. Further key catalytic steps of the synthesis include an oxidative Heck reaction at room temperature and a hydrazine-mediated organocatalysed reduction. The Royal Society of Chemistry 2013.

PROCESS FOR THE PREPARATION OF AN ENANTIOMERIC TRISUBSTITUTED 3,4-DIHYDRO-ISOQUINOLINE DERIVATIVE

The present invention relates to a process for the preparation of the compound of formula (7) which process comprises the hydrogenation of the compound of formula (4) using bis[chloro-1,5-cyclooctadiene-iridium], (S)-i-dicyclohexylphosphino-2-[(S)-α-(dime

SOLID FORMS OF ( 2R) -2- { ( IS ) -6, 7 -DIMETHOXY- 1- [2- (4-TRIFLU0R0METHYL-PHENYL) -ETHYL] -3, 4-DIHYDR0-1H -ISOQUINOLIN-2-YL} -N-METHYL-2-PHENYL-ACETAMIDE HYDROCHLORIDE

The invention relates to hydrated crystalline forms of (2R)-2-{(1 S)-6,7-dimethoxy-1 - [2-(4-thfluoromethyl-phenyl)-ethyl]-3,4-dihydro-1 H-isoquinolin-2-yl}-Λ/-methyl-2- phenyl-acetamide hydrochloride, to the amorphous form of this compound, and to further crystalline forms of this compound, to processes for the preparation thereof, pharmaceutical compositions containing said crystalline forms or said amorphous form, and their use as orexin receptor antagonists.

TRISUBSTITUTED 3,4-DIHYDRO-1H-ISOQUINOLIN COMPOUND, PROCESS FOR ITS PREPARATION, AND ITS USE

The present invention relates to the compound of formula 7*acetate (see below), a process for its preparation, and its use

Tetrahydroisoquinoline Derivatives to Enhance Memory Function

The invention relates to the use of tetrahydroisoquinoline derivatives for the preparation of a medicament to enhance, maintain and/or restore all stages and/or types of short-, middle- and/or long-term memory.

PROCESS FOR THE PREPARATION OF AN ENANTIOMERIC TRISUBSTITUTED 3,4-DIHYDRO-ISOQUINOLINE DERIVATIVE

The present invention relates to a process for the preparation of the compound of formula (7) which process comprises the hydrogenation of the compound of formula (4) using bis[chloro-1,5-cyclooctadiene-iridium], (S)-i -dicyclohexylphosphino- 2-[(S)-α-(di

TRISUBSTITUTED 3,4-DIHYDRO-1H-ISOQUINOLIN COMPOUND, PROCESS FOR ITS PREPARATION, AND ITS USE

The present invention relates to the compound of formula (7*)acetate (see below), a process for its preparation, and its use.

SUBSTITUTED 1,2,3,4-TETRAHYDROISOQUINOLINE DERIVATIVES

The invention relates to novel 1,2,3,4-tetrahydroisoquinoline derivatives of formula (I) wherein R1, R2, R3 and X are as defined in the claims, and their use as active ingredients in the preparation of pharmaceutical compo