949-67-7

Usage

Uses

L-TYROSINE ETHYL ESTER is a useful research chemical.

Chemical Properties

White powder

Definition

ChEBI: An L-tyrosyl ester that is L-tyrosine in which the hydrogen of the carboxy group has been replaced by an ethyl group.

InChI:InChI=1/C9H11NO3.C2H4O/c10-8(9(12)13)5-6-1-3-7(11)4-2-6;1-2-3/h1-4,8,11H,5,10H2,(H,12,13);2H,1H3/t8-;/m0./s1

Upstream product

• 64-17-5 ethanol 
• 60-18-4 L-tyrosine 
• 122-51-0 orthoformic acid triethyl ester 
• 840-97-1 N-acetyl-L-tyrosine ethyl ester 
• 4089-07-0 L-tyrosine ethyl ester monohydrochloride 
• 67-56-1 methanol 
• 556-02-5 ?Tyr 
• 34081-17-9 tyrosine ethyl ester 

Downstream Products

• 3061-88-9 L-alanyl-L-tyrosine 
• 91604-98-7 N-D-alanyl-L-tyrosine 
• 70779-94-1 OC(TyrOEt)2 
• 111639-24-8 N,N-phthaloyl-L-tyrosin-ethyl ester 
• 71800-49-2 N-formyl-L-tyrosine ethyl ester 
• 103820-93-5 ethyl N-benzyloxycarbonyl-L-leucyl-L-tyrosinate 
• 63293-21-0 N-nicotinoyl-L-tyrosin-ethyl ester 
• 908572-71-4 N-((Ξ)-α-bromo-isovaleryl)-L-tyrosine ethyl ester 
• 124103-83-9 N-(penta-O-acetyl-D-gluconoyl)-L-tyrosine ethyl ester 
• 124103-82-8 N-(penta-O-acetyl-D-galactonoyl)-L-tyrosine ethyl ester 
• 150956-51-7 (2-iodoacetyl)-L-tyrosine 
• 908572-86-1 N-(α-bromo-isobutyryl)-L-tyrosine ethyl ester 
• 109068-48-6 N-(N-benzoyl-glycyl)-L-tyrosine 
• 79598-35-9 benzyloxycarbonylvalyltyrosine ethyl ester 

Relevant academic research and scientific papers

Inhibition of acetylcholinesterase by coumarin-linked amino acids synthetized via triazole associated with molecule partition coefficient

A previous study for the identification of acetylcholinesterase (AChE) inhibitors demonstrated that the hybrid between tyrosol, the 1,2,3-triazole nucleus, and the coumarin group, namely 7-({1-[2-(4-hydroxyphenyl)ethyl]-1H-1,2,3-triazol-4-yl}methoxy)-4-methyl-2H-chromen-2-one (10), has a high enzyme inhibitory activity. Here, we synthesized analogues of 10 via triazole with pharmacophoric groups represented by tyrosine, phenylalanine, tryptophan, and glycine in addition to evaluating the impact of coumarin-linked amino acids on AChE inhibition. We obtained eight triazoles, six of which are undescribed. In general, the presence of carboxylic acid decreased the inhibitory activity, while aromatic amino acids increased enzymatic inhibition compared to glycine. The derivative containing tyrosine, structurally most similar to 10, presented the lowest inhibition percentage, indicating that phenolic hydroxyl is not the preponderant factor for inhibition. Molecular docking was not enough to explain in vitro experiments. On the other hand, MlogP (logP calculated by the Moriguchi method) was related positively to enzymatic inhibition. To increase the hydrophobicity of the molecules, we tested the esterified triazole derivatives comparatively with the enzyme. The compound ethyl 2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)- 1H-1,2,3-triazol-1-yl)acetate (6) presented an increment of inhibitory activity of 46.97 ± 1.75% at 100 μmol L-1. We also associated the best activity with the lowest van der Waals volume and molar mass values.

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.

Preparation method of rosastat key intermediate

The invention provides a preparation method of a rosastat key intermediate. The intermediate I is 4-hydroxy-1-methyl-7-phenoxy isoquinoline-3-carboxylic ester. The preparation method comprises the following steps: with tyrosine as an initial raw material, sequentially carrying out esterification, acylation, etherification, cyclization, aromatization and oxidation rearrangement reaction to preparethe rosastat key intermediate. The preparation method has the advantages of cheap and easily available raw materials, environmental protection, avoiding of use of phosphorus oxychloride, polyphosphoric acid and other environmentally unfriendly reagents in the cyclization reaction, simple process, simple operation and mild reaction conditions; and the method has the advantages of less three wastesand higher product yield and purity, and is suitable for industrial production.

Stereospecific Synthesis of 3,4-Dihydro-2 H-naphtho-1,4-oxazin-2-ones by Unification of Benzoxepine-4-carboxylates with Chiral Amino Acid Ethyl Esters

A novel and efficient stereocontrolled method has been developed for the preparation of chiral 3,4-dihydro-2H-naphtho[1,2-b][1,4]oxazin-2-ones by the reaction of benzoxepine-4-carboxylates with chiral amino acid ethyl esters for the first time. The chiral 3,4-dihydro-2H-naphtho-1,4-oxazinones have been achieved in one step by the formation of C-N, C-C, and C-O bonds.

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.

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids

The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-ILs is the main challenge for their application in drug delivery. To address this issue, 11 amino acid esters (AAEs) were synthesized and investigated as biocompatible counter cations for the poorly water-soluble drug salicylic acid (Sal) to form Sal-ILs. The AAEs were characterized using 1H and 13C NMR, FTIR, elemental, and thermogravimetric analyses. The cytotoxicities of the AAE cations, Sal-ILs, and free Sal were investigated using mammalian cell lines (L929 and HeLa). The toxicities of the AAE cations greatly increased with inclusion of long alkyl chains, sulfur, and aromatic rings in the side groups of the cations. Ethyl esters of alanine, aspartic acid, and proline were selected as a low cytotoxic AAE. The cytotoxicities of the Sal-ILs drastically increased compared with the AAEs on incorporation of Sal into the cations, and were comparable to that of free Sal. Interestingly, the water miscibilities of the Sal-ILs were higher than that of free Sal, and the Sal-ILs were miscible with water at any ratio. A skin permeation study showed that the Sal-ILs penetrated through skin faster than the Sal sodium salt. These results suggest that AAEs could be used in biomedical applications to eliminate the use of traditional toxic solvents for transdermal delivery of poorly water-soluble drugs.

A cancer-targetable copolymer containing tyrosine segments for labeling radioactive halogens

A series of cancer-targetable copolymers containing rhodamine and tyrosine segments were synthesized and further labeled with isotope 125I. Copolymers with different molecular weights (PRTH-1, PRTH-2 and PRTH-3) formed aggregates in water with average diameters of 66 nm, 191 nm and 137 nm, respectively. The cancer cell targeting properties of the copolymers were investigated by comparing BEL-7402 liver cancer cells and L-02 human normal liver cells. The results indicate that their targeting properties are related to the average diameters of the PRTH copolymers that self-assembled in water. PRTH-2 copolymers were selected as having the best targeting properties for cancer cells. The in vivo study of HepA mouse models based on single-photon emission computed tomography (SPECT) also showed good tumor-targeting properties of PRTH-2 labeled with 125I.

NMR determinations of the absolute configuration of α-chiral primary amines

(Figure presented) We have established a methodology to determine the absolute configuration of α-chiral primary amines by derivatization to the corresponding imines with each enantiomer of 2′-methoxy-1,1′- binaphthalene-8-carbaldehyde (1). This methodology proceeds on the basis of modified Moshers method, and sufficiently large ΔδR S values can be obtained to elucidate the stereochemistry of the amines.

Total synthesis of tricyclic azaspirane derivatives of tyrosine: FR901483 and TAN1251C

A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.