72594-77-5

Usage

Uses

Used in Organic Chemistry:
BOC-L-TYROSINE ETHYL ESTER is used as a building block in peptide synthesis for its ability to be incorporated into larger peptide structures. This allows researchers to study the biological activity and pharmacological properties of these peptides.
Used in Drug Discovery:
In the field of drug discovery, BOC-L-TYROSINE ETHYL ESTER serves as a crucial component in the development of new pharmaceutical compounds. Its protective BOC group and ethyl ester functionality contribute to the compound's versatility and stability during synthesis processes.
Used in Pharmaceutical Development:
BOC-L-TYROSINE ETHYL ESTER is utilized in pharmaceutical development to improve the solubility and stability of potential drug candidates. Its ethyl ester moiety plays a significant role in enhancing these properties, which is essential for the compound's effectiveness and safety in medical applications.

InChI:InChI=1/C16H23NO5/c1-5-21-14(19)13(17-15(20)22-16(2,3)4)10-11-6-8-12(18)9-7-11/h6-9,13,18H,5,10H2,1-4H3,(H,17,20)/t13-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4089-07-0 L-tyrosine ethyl ester monohydrochloride 
• 909114-65-4 tert-butyl 4,6-dimethoxy-1,3,5-triazinyl carbonate 
• 5619-08-9 tyrosine ethyl ester hydrochloride 
• 169158-01-4 (S)-α-tert-butoxycarbonylamino-4-[[(trifluoromethyl)sulfonyl]oxy]benzenepropionic acid ethyl ester 
• 60-18-4 L-tyrosine 
• 949-67-7 L-tyrosine ethyl ester 
• 64-17-5 ethanol 
• 3978-80-1 Boc-Tyr-OH 

Downstream Products

• 134081-15-5 N-(tert-butyloxycarbonyl)-L-tyrosinal 
• 1394035-45-0 (S)-N₁-((1-(4-benzyloxy)benzyl)-2-hydroxyethyl)-N₂-phenylthiourea 
• 1394035-46-1 (S)-4-(4-benzyloxybenzyl)-2-phenylimino-2-oxazolidine 
• 1256282-48-0 (S)-4-(4-hydroxybenzyl)-2-phenylimino-2-oxazolidine 
• 169158-05-8 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-ethynylphenyl)propanoic acid 
• 340733-32-6 4-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-[(2S)-4-[2-(tert-butoxy)-2-oxoethyl]-2-(2-methoxy-2-oxoethyl)-3-oxopiperazinyl]-3-oxopropyl]benzoic acid 
• 169158-06-9 {1-[2-tert-butoxycarbonylamino-3-(4-ethynyl-phenyl)-propionyl]-4-tert-butoxycarbonylmethyl-3-oxo-piperazin-2-yl}-acetic acid methyl ester 
• 169158-11-6 methyl 2-[(2S)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-(hydroxymethyl)phenyl]propanoyl]-4-[2-(tert-butoxy)-2-oxoethyl]-3-oxopiperazinyl]acetate 
• 340733-28-0 methyl 2-[(2S)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-ethylphenyl)propanoyl]-4-[2-(tert-butoxy)-2-oxoethyl]-3-oxopiperazinyl]acetate 
• 169158-04-7 methyl 2-[(2S)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-vinylphenyl)propanoyl]-4-[2-(tert-butoxy)-2-oxoethyl]-3-oxopiperazinyl]acetate 

Relevant academic research and scientific papers

Novel derivatives of urea and use thereof

The present invention relates to a novel urea derivative compound and 5HT thereof. 2A The present invention relates to the use of antagonists as antagonists for the prevention or treatment of neuropsychiatric disorders, degenerative brain diseases, propagated disorders and/or metabolic diseases.

Peripheral Selective Oxadiazolylphenyl Alanine Derivatives as Tryptophan Hydroxylase 1 Inhibitors for Obesity and Fatty Liver Disease

Tryptophan hydroxylase 1 (TPH1) has been recently suggested as a promising therapeutic target for treating obesity and fatty liver disease. A new series of 1,2,4-oxadiazolylphenyl alanine derivatives were identified as TPH1 inhibitors. Among them, compound 23a was the most active in vitro, with an IC50 (half-maximal inhibitory concentration) value of 42 nM, showed good liver microsomal stability, and showed no significant inhibition of CYP and hERG. Compound 23a inhibited TPH1 in the peripheral tissue with limited BBB penetration. In high-fat diet-fed mice, 23a reduced body weight gain, body fat, and hepatic lipid accumulation. Also, 23a improved glucose intolerance and energy expenditure. Taken together, compound 23a shows promise as a therapeutic agent for the treatment of obesity and fatty liver diseases.

Design, Synthesis, and Biological Evaluation of New Peripheral 5HT2A Antagonists for Nonalcoholic Fatty Liver Disease

Nonalcoholic fatty liver disease (NAFLD) is increasingly prevalent worldwide, causing serious liver complications, including nonalcoholic steatohepatitis. Recent findings suggest that peripheral serotonin (5-hydroxytryptamine, 5HT) regulates energy homeostasis, including hepatic lipid metabolism. More specifically, liver-specific 5HT2A knockout mice exhibit alleviated hepatic lipid accumulation and hepatic steatosis. Here, structural modifications of pimavanserin (CNS drug), a 5HT2A antagonist approved for Parkinson's disease, led us to synthesize new peripherally acting 5HT2A antagonists. Among the synthesized compounds, compound 14a showed good in vitro activity, good liver microsomal stability, 5HT subtype selectivity, and no significant inhibition of CYP and hERG. The in vitro and in vivo blood-brain barrier permeability study proved that 14a acts peripherally. Compound 14a decreased the liver weight and hepatic lipid accumulation in high-fat-diet-induced obesity mice. Our study suggests new therapeutic possibilities for peripheral 5HT2A antagonists in NAFLD.

NOVEL TRYPTOPHAN HYDROXYLASE INHIBITOR AND PHARMACEUTICAL COMPOSITION INCLUDING SAME

The present invention relates to a novel tryptophan hydroxylase inhibitor and a pharmaceutical composition including same, wherein the novel tryptophan hydroxylase inhibitor has an excellent inhibitory effect on TPH1, and thus can be usefully used for the prevention or treatment of disorders, such as metabolic disorders, cancer, digestive or cardiovascular system disorders, related to TPH1 activity. In particular, the novel tryptophan hydroxylase inhibitor has an excellent treatment effect on inflammatory bowel disorders, and thus can be usefully used for the treatment of inflammatory bowel disorder.

New reagent for the introduction of Boc protecting group to amines: Boc-OASUD

A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD, being a solid and more stable, is a better alternative to di-tert-butyl dicarbonate which is low melting and has to be dispensed in plastic containers than glass because of its poor stability.

Nonsolvent application of ionic liquids: Organo-catalysis by 1-alkyl-3-methylimidazolium cation based room-temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency

1-Alkyl-3-methylimidazolium cation based ionic liquids efficiently catalyze N-tert-butyloxycarbonylation of amines with excellent chemoselectivity. The catalytic role of the ionic liquid is envisaged as "electrophilic activation" of di-tert-butyl dicarbonate (Boc2O) through bifurcated hydrogen bond formation with the C-2 hydrogen of the 1-alkyl-3-methylimidazolium cation and has been supported by a downfield shift of the imidazolium C-2 hydrogen of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim][NTf2]) from δ 8.39 to 8.66 in the presence of Boc2O in the 1H NMR and a drastic reduction of the catalytic efficiency with 1-butyl-2,3-dimethylimidazolium ionic liquids that are devoid of the C-2 hydrogen. The differential time required for reaction with aromatic and aliphatic amines has offered means for selective N-t-Boc formation during inter and intramolecular competitions. Preferential N-t-Boc formation with secondary aliphatic amine has been achieved in the presence of primary aliphatic amine. Comparison of the catalytic efficiency for N-t-Boc formation with a common substrate revealed that [bmim][NTf2] is superior to the reported Lewis acid catalysts.

Useful reagents for introduction of Boc and Fmoc protective groups to amines: Boc-DMT and Fmoc-DMT

New amino-protecting reagents, Boc-DMT and Fmoc-DMT, were prepared, and found to be useful for the introduction of Boc and Fmoc groups into amines. Both the reagents can protect various amines including amino acids in good yield in aqueous media. Since the reagents are neither unstable nor irritating, they are practically useful. Georg Thieme Verlag Stuttgart.

HClO4-SiO2 as a new, highly efficient, inexpensive and reusable catalyst for N-tert-butoxycarbonylation of amines

Perchloric acid adsorbed on silica-gel (HClO4-SiO2) was found to be a new, highly efficient, inexpensive and reusable catalyst for chemoselective N-tert-butoxycarbonylation of amines at room temperature and under solvent-free conditions. The Royal Society of Chemistry 2006.

Indium(III) halides as new and highly efficient catalysts for N-tert-butoxycarbonylation of amines

Indium(III) bromide and chloride efficiently catalysed the N-tert-butoxycarbonylation of amines with (Boc)2O at room temperature and under solvent-free conditions. Various aromatic, heteroaromatic and aliphatic amines were converted to N-tert-butylcarbamates in excellent yields in short times. Chiral amines, esters of α-amino acids and β-amino alcohols afforded optically pure N-t-Boc derivatives in high yields. The reactions were chemoselective and no competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation were observed. Chemoselective conversion to N-tert-butylcarbamates took place with amino alcohols without any formation of oxazolidinones. Georg Thieme Verlag Stuttgart.

NOVEL BIAROMATIC COMPOUNDS WHICH ACTIVATE PPARγ TYPE RECEPTORS, AND USE THEREOF IN COSMETIC OR PHARMACEUTICAL COMPOSITIONS

The invention relates to novel biaromatic compounds which correspond to the general formula (I), and also to a process for preparing them and to their use in pharmaceutical compositions intended for use in human or veterinary medicine (in dermatology, and also in the field of cardiovascular diseases, immune diseases and/or diseases associated with lipid metabolism), or alternatively in cosmetic compositions.