727425-00-5

Upstream product

• 112-77-6 (Z)-9-octadecenoyl chloride 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 3728-20-9 D-tyrosine methylester hydrochloride 
• 112-80-1 cis-Octadecenoic acid 
• 1080-06-4 L-Tyr-OMe 
• 60-18-4 L-tyrosine 
• 556-02-5 tyrosine 

Downstream Products

• 727425-01-6 (S)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((Z)-octadec-9-enoylamino)-propionic acid methyl ester 
• 935547-97-0 3-[4-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethoxy)-phenyl]-2-octadec-9-enoylamino-propionic acid methyl ester 
• 147732-57-8 N-oleoyl-L-tyrosine 
• 727425-02-7 phosphoric acid di-tert-butyl ester 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-octadec-9-enoylamino-propyl ester 
• 727425-03-8 Phosphoric acid di-tert-butyl ester (S)-3-(4-hydroxy-phenyl)-2-((Z)-octadec-9-enoylamino)-propyl ester 

Relevant academic research and scientific papers

Synthesis, physicochemical, and biological activities of novel N-acyl tyrosine monomeric and Gemini surfactants in single and SDS/CTAB–mixed micellar system

A series of single-chained N-acyl tyrosine surfactants with varying chain lengths (C10-C18) and degree of unsaturation, as well as an N-acyl Gemini tyrosine surfactant with chain length C12, were synthesized, and the struc

The impact of sugar and fatty acid on the bioactivity of N-fatty acyl-L-tyrosine aglycone

Abstract: In the present study, a series of fatty acids-based (short, medium and long unsaturated chains) glycosylated N-fatty acyl-L-tyrosines and N-lipoyl-L-tyrosine methyl esters were synthesized and evaluated for their cytotoxic and antimicrobial activities. The aglycone moiety was synthesized using different chemical reagents. The glycosylation of aglycone moiety with different carbohydrates was performed using the Lewis acid, BF 3.Et 2O. All the synthesized compounds were tested against a panel of four cancer cell lines. The glycosylated N-fatty acyl-L-tyrosines showed moderate activity against all the cell lines and the IC 50 values were in the range of 15.6-45.6μM. However, the oleic acid analogues (10a, 10d) exhibited IC 50 values of 15.6, 17.6μM, respectively, against MDA-MB-231 cell line. Glycosylated N-lipoyl-L-tyrosine methyl esters (6b–6d) showed promising activity against all the tested cell lines and the IC 50 values ranged between 9.4-13.8μM. The compound 6d exhibited significant cytotoxicity and IC 50 values were 10.5, 9.4, 10.9 and 12.1μM against A549, PC3, MDA-MB-231 and HepG2 cell lines, respectively. Moreover, the non-glycosylated N-fatty acyl-L-tyrosine and methyl N-fatty acyl-L-tyrosinate derivatives showed excellent and moderate antimicrobial activity against some of the tested bacterial strains. Graphical Abstract: The glycosylated N-fatty acyl-L-tyrosines with short, medium and long chain unsaturated fatty acids and glycosylated N-lipoyl-L-tyrosine methyl esters were synthesized and further evaluated for their biological activities to examine the impact of sugar and fatty acid on the bioactivity of N-fatty acyl-L-tyrosine derivatives. [Figure not available: see fulltext.].

Design and synthesis of lipids for the fabrication of functional lipidic cubic-phase biomaterials

A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of α-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

Synthesis and biological evaluation of phosphonate derivatives as autotaxin (ATX) inhibitors

Autotaxin (ATX) is an autocrine motility factor that promotes cancer cell invasion, cell migration, and angiogenesis. ATX, originally discovered as a nucleotide phosphodiesterase, is known now to be responsible for the lysophospholipid-preferring phosphol

In situ synthesis of gold And silver nanoparticles by using redox-active amphiphiles and their phase transfer to organic solvents

An in situ reduction approach to synthesizing gold and silver nanoparticles by using a series of newly designed, redox-active amphiphiles at basic pH is described. These amphiphiles are the conjugates of a fatty acid (e.g., oleic acid, stearic acid, and l

NOVEL LYSOPHOSPHATIDIC ACID RECEPTOR SELECTIVE ANTAGONISTS

The present invention is directed to compositions comprising lysophosphatidic acid analogs and methods of using such analogs as agonist or antagonists of LPA receptor activity. In addition the invention is directed to LPA receptor agonists that vary in the degree of selectivity at individual LPA receptors (i.e. LPA1, LPA2 and LPA3). More particularly the present invention is directed to LPA analogs wherein the glycerol is replaced with ethanolamine and a variety of substitutions have been linked at the second carbon atom.

Initial structure-activity relationships of lysophosphatidic acid receptor antagonists: Discovery of a high-affinity LPA1/LPA3 receptor antagonist

A recently reported dual LPA1/LPA3 receptor antagonist (VPC12249, 1) has been modified herein so as to optimize potency and selectivity at LPA receptors. Compounds containing variation in the acyl lipid chain and linker region have been synthesized and screened for activity at individual LPA receptors. LPA1-selective (14b) and LPA 3-selective (10g,m) compounds of modest potency have been discovered. Additionally, 2-pyridyl derivative 10t exhibits a Ki value of 18nM at the LPA1 receptor and is significantly more potent than 1 at the LPA3 receptor. This paper describes the synthetic methods, biological evaluation, and structure-activity relationships (SARs) of LPA receptor antagonists.

A novel series of 2-pyridyl-containing compounds as lysophosphatidic acid receptor antagonists: Development of a nonhydrolyzable LPA3 receptor-selective antagonist

A recently reported dual LPA1/LPA3 receptor antagonist (1) has been modified so as to modulate the basicity, sterics, and dipole moment of the 2-pyridyl moiety. Additionally, the implications of installing nonhydrolyzable phosphate head group isosteres with regard to antagonist potency and selectivity at LPA receptors is described. This study has resulted in the development of the first nonhydrolyzable and presumably phosphatase-resistant LPA3-selective antagonist reported to date.