114673-69-7

Usage

Uses

Used in Pharmaceutical Research:
(2S)-2-AMINO-2-(3,4-DIMETHOXYPHENYL)ETHAN-1-OL is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential pharmacological activities.
Used in Organic Synthesis:
(2S)-2-AMINO-2-(3,4-DIMETHOXYPHENYL)ETHAN-1-OL is used as a building block in the creation of complex organic molecules, contributing to the development of new chemical entities.
Used in Drug Development:
(2S)-2-AMINO-2-(3,4-DIMETHOXYPHENYL)ETHAN-1-OL is utilized in the research and development of new drugs and medications, given its unique structural features and potential therapeutic applications.

Upstream product

• 147383-98-0 (2S)-(+)-3,4-dimethoxyphenylglycine 
• 250665-92-0 [2S,1'S,2'S]-(+)-2-(3,4-dimethoxyphenyl)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 
• 250665-97-5 [2S,1'S,2'S]-(+)-2-amino-2-(3,4-dimethoxyphenyl)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 
• 234089-44-2 (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-2-(3,4-dimethoxyphenyl)-N-methylacetamide 

Downstream Products

• 394739-96-9 (2S)-(-)-2-[(E)-2,3-dimethoxybenzylideneamino]-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-97-0 (2S)-(+)-2-(2,3-dimethoxybenzyl)amino-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-98-1 (2S)-(+)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-99-2 (3S,4S)-(+)-7,8-dimethoxy-3-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol 

Relevant academic research and scientific papers

Norepinephrine alkaloids as antiplasmodial agents: Synthesis of syncarpamide and insight into the structure-activity relationships of its analogues as antiplasmodial agents

Syncarpamide 1, a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC50 values of 2.04 μM (D6 clone), 3.06 μM (W2 clone) and observed by us 3.90 μM (3D7 clone) and 2.56 μM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, (R)-2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds (3–57), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer (S)-58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, (S)-41 and its enantiomer, (R)-42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC50 values of 3.16, 2.28 μM (3D7) and 1.78, 2.07 μM (K1), respectively than the natural product, syncarpamide 1. Three compounds (S)-13, (S)-17, (S)-21 exhibited antiplasmodial activities with IC50 values of 6.39, 6.82, 6.41 μM against 3D7 strain, 4.27, 7.26, 2.71 μM against K1 strain and with CC50 values of 147.72, 153.0, >200 μM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1. The natural product syncarpamide 1 and four analogues/homologues out of the synthesized library of 55, (S)-41, (R)-42, (S)-55 and (S)-57 were assayed in vivo assay against chloroquine-resistant P. yoelii (N-67) strain of Plasmodium. However, none of the five molecules, 1, (S)-41, (R)-42, (S)-55 and (S)-57 exhibited any promising in vivo antimalarial activity against P. yoelii (N-67) strain. Compounds 4, 6, 7 and 11 showed high cytotoxicities with CC50 values of 5.87, 5.08, 6.44 and 14.04 μM, respectively. Compound 6 was found to be the most cytotoxic as compared to the standard drug, podophyllotoxin whereas compounds 4 and 7 showed comparable cytotoxicities to podophyllotoxin.

Asymmetric synthesis of arylglycines and their use as chiral templates for the stereocontrolled synthesis of 7,8-disubstituted 3-Aryl-1,2,3,4-tetrahydroisoquinolin-4-ols

A synthetic technique for the asymmetric synthesis of arylglycines has been optimized, reaching the target amino acids in only four steps with good yields and with enantiomeric excesses higher than 99%. The key step consisted of a stereocontrolled electrophilic amination reaction of (S,S)-(+)-pseudoephedrine-based arylacetamide enolates with di-tertbutylazodicarboxylate. The arylglycines thus obtained turned out to be excellent chiral templates for the production of chiral, nonracemic 7,8-disubstituted 3-aryl-1,2,3,4-tetrahydroisoquinolines, through use of a synthetic sequence involving: (1) reduction of the arylglycines to the parent arylglycinols, (2) N-benzylation with appropriately substituted aromatic aldehydes and (3) Swern oxidation followed by acid catalysed cyclization of the obtained a-amino aldehydes.