138908-56-2

Usage

Uses

Used in Pharmaceutical Industry:
L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-methyl ester is used as an intermediate in the synthesis of N-Methyl-L-DOPA (M303825) for pharmaceutical applications. N-Methyl-L-DOPA is a methylated form of L-DOPA, which is known for its role in the treatment of Parkinson's disease. The compound acts as a potential alternative substrate or competitive inhibitor of tyrosinase, an enzyme involved in the production of melanin and other biological processes.
Used in Research and Development:
L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-,
methyl ester may also be utilized in research and development for the study of tyrosinase and its role in various biological processes. By understanding the interactions between L-Tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-3-methoxy-O-methyl-methyl ester and tyrosinase, researchers can gain insights into the development of new therapeutic strategies for conditions related to tyrosinase dysregulation.

Upstream product

• 30033-24-0 (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoic acid 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 127095-97-0 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid 
• 37169-36-1 methyl (S)-2-(tert-butoxycarbonylamino)-3-(3,4-dihydroxyphenyl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 32161-30-1 (S)-3,4-dimethoxyphenylalanine 
• 59-92-7 levodopa 
• 7101-51-1 L-DOPA methyl ester 

Downstream Products

• 105779-71-3 (S)-(-)-[2-(3,4-dimethoxyphenyl)-1-hydroxymethylethyl]carbamic acid tert-butyl ester 
• 127095-97-0 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid 
• 944416-22-2 [(S)-2-(3,4-dimethoxyphenyl)-1-methylcarbamoyl-ethyl]carbamic acid tert-butyl ester 
• 57061-12-8 trans-1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester 
• 1219687-56-5 [(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol 
• 1173933-75-9 [(1S,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol 
• 70471-01-1 C₁₉H₂₁NO₄ 
• 82586-62-7 (S)‐6,7‐dimethoxy‐1,2,3,4-tetrahydroisoquinoline‐3‐carboxylate hydrochloride 
• 142763-11-9 (S)-4-(3,4-dimethoxybenzyl)oxazolidin-2-one 
• 1373614-10-8 (4S)-4-(3,4-dimethoxybenzyl)-3-(propa-1,2-dienyl)oxazolidin-2-one 
• 1373614-09-5 C₁₅H₁₇NO₄ 

Relevant academic research and scientific papers

Racemic and diastereoselective synthesis of aryl and heteroaryl tetrahydroisoquinolines via the Pictet-Spengler reaction

New tetrahydroisoquinolines were synthesized by the Pictet-Spengler reaction. Influence of a wide range of aryl and heteroaryl aldehydes, was investigated in the cyclization step with 3,4-dimethoxyphenylethylamine 1, L-DOPA 2 and L-3,4-dimethoxyphenylalan

Synthesis and Biological Evaluation of Endocannabinoid Uptake Inhibitors Derived from WOBE437

WOBE437 ((2E,4E)-N-(3,4-dimethoxyphenethyl)dodeca-2,4-dienamide, 1) is a natural product-derived, highly potent inhibitor of endocannabinoid reuptake. In this study, we synthesized almost 80 analogues of 1 with different types of modifications in the dodecadienoyl domain as well as the dimethoxyphenylethyl head group, and we investigated their effects on anandamide uptake into U937 cells. Intriguingly, none of these analogues was a more potent inhibitor of anandamide uptake than WOBE437 (1). At the same time, a number of WOBE437 variants exhibited potencies in the sub-100 nM range, with high selectivity over inhibition of the endocannabinoid-degrading enzyme fatty acid amide hydrolase; two compounds were virtually equipotent with 1. Interestingly, profound activity differences were observed between analogues in which either of the two methoxy substituents in the head group had been replaced by the same bulkier alkoxy group. Some of the compounds described here could be interesting departure points for the development of potent endocannabinoid uptake inhibitors with more drug-like properties.

Polyphenol compound containing tetrahydropapaverine-3-methyl carboxylate, preparation method and applications thereof

The invention discloses a polyphenol compound containing tetrahydropapaverine-3-methyl carboxylate, a preparation method and applications thereof, wherein the polyphenol compound has a structure represented by a formula I, and R is hydrogen, halogen, C1-8 alkyl, C1-8 cycloalkyl, C1-8 halogenated alkyl, C1-8 alkoxy, C1-8 halogenated alkoxy, C2-4 alkenyl, phenyl, halogenated phenyl, nitrophenyl, C1-4 alkyl substituted phenyl, C1-4 halogenated alkyl substituted phenyl, naphthalene or acylamino. According to the invention, the polyphenol compound is novel in structure and generally has relativelygood inhibitory activity on influenza A virus H1N1, and the inhibitory effect of most compounds is superior to the inhibitory effect of a positive control Perimivir, so that the results show that thecompound has obvious inhibiting effect on influenza A virus, can be prepared into anti-influenza A virus medicine to be applied, has good application prospects in prevention and treatment of influenzavirus infection, and expands the application of tetrahydropapaverine structures as anti-influenza virus medicine.

Nitrogen (oxygen) heterocyclic pentane - 2 - one (thione) compound, pharmaceutical composition, preparation method and use thereof

The invention belongs to the field of pharmacology, and relates to aza (oxa)-cyclopentane-2- ketone (thione) compounds shown in the formula I, medicine compositions thereof, a preparation method, applications in preparation of medicines treating diabetes and glucolipid metabolism, and especially applications in preparation of medicines treating II-type diabetes.

An Au(I)-catalysed allenamide cyclisation giving access to an α-vinyl-substituted tetrahydroisoquinoline building block

An Au(I)-catalysed intramolecular hydroarylation of an enantiopure allenamide has been achieved and has given access to a key α-vinyl- substititued tetrahydroisoquinoline. Additionally this has been accomplished in very high yield and high diastereoselectivity. Georg Thieme Verlag Stuttgart · New York.

An organogel formed from a cyclic β-aminoalcohol

A new organogelator with unique structural feature of a cyclic β-aminoalcohol is presented as the first example of gelation by aminoalcohol through hydrogen-bonding between hydroxy and amine.

Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): Comparison with related catecholamines

(±)-3,4-Methylenedioxymethamphetamine (MDMA, also known as "ecstasy") is a chiral drug that is essentially metabolized in humans through O-demethylenation into 3,4-dihydroxymethamphetamine (HHMA). There has recently been a resurgence of interest in the po

Oxidative nucleophilic substitution (SNOX) of the benzylic position as a tunable synthesis of tetrahydroisoquinoline natural alkaloid analogues

Synthetic investigations of 1,3-dichloro-5,6-dicyanobenzoquinone-mediated benzylic oxidation is reported for the synthesis of natural alkaloid analogues. Extensive explorations of the oxidative nucleophilic substitution of the benzylic position of β-phenylethylamine derivatives and the synthesis of functionalized tetrahydroisoquinolines of ecteinascidin 743 precursors have been carried out. Starting from L-DOPA, a tunable oxazolidinone group was installed under oxidative benzylic conditions. This derivative 13 was submitted to benzylic oxidation reactions using a wide range of carboxylic acids and subsequent chemical transformations of these compounds were attempted. Moreover, an efficient synthesis of an aromatic ketone derivative 20 was achieved and gave rise to tetrahydroisoquinoline 24 through a direct Pictet-Spengler cyclisation reaction. Subsequently, 24 was transformed into functionahzed α-amino alcohols 31a and 31b, precursors of ecteinascidin 743 analogues. In addition, in order to assess the viability of our synthetic strategy, the reaction of 24 with methyl thioglycolate was performed and the stereoselectivity confirmed by X-ray analysis of 33a. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Diastereoselective intramolecular α-amidoalkylation reactions of L-DOPA derivatives. Asymmetric synthesis of pyrrolo[2,1-a]isoquinolines

Stereocontrolled intramolecular α-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S,10b

A new efficient synthetic process for the construction of the pentacyclic core of marine alkaloid ecteinascidins

The pentacyclic core of ecteinascidins was constructed from two fundamental building blocks, the 1,2,3,4-tetrahydroisoquinoline derivative and the substituted phenylalanine derivative, via 8 steps using readily available L-Dopa as starting material. The k