851589-00-9

Upstream product

• 851588-99-3 (R)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-2-((Z)-octadec-9-enoylamino)-propionic acid methyl ester 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 556-02-5 tyrosine 
• 851588-98-2 (R)-3-(4-Hydroxy-phenyl)-2-((Z)-octadec-9-enoylamino)-propionic acid methyl ester 
• 3728-20-9 D-tyrosine methylester hydrochloride 

Downstream Products

• 851589-01-0 phosphoric acid di-tert-butyl ester 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-octadec-9-enoylamino-propyl ester 
• 871022-90-1 C₃₅H₅₀NO₅P 
• 851589-02-1 C₃₆H₆₁F₃NO₈PS 

Relevant academic research and scientific papers

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.

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.

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.