50765-22-5

Usage

Uses

Methyl 3-hydroxy-5-iodobenzoate

InChI:InChI=1/C8H7IO3/c1-12-8(11)5-2-6(9)4-7(10)3-5/h2-4,10H,1H3

Upstream product

• 217314-45-9 methyl 3-amino-5-iodobenzoate 
• 67-56-1 methanol 
• 50765-21-4 3-hydroxy-5-iodobenzoic acid 
• 6313-17-3 3-iodo-5-nitro-benzoic acid 
• 50765-19-0 methyl 3-iodo-5-nitrobenzoate 

Downstream Products

• 752242-32-3 5-iodo-3-isopropoxybenzoic acid methyl ester 

Relevant academic research and scientific papers

TRIAZOLE DERIVATIVES AS P2Y14 RECEPTOR ANTAGONISTS

Described are compounds, which are antagonists of the P2Y14 receptor, for example, a compound of formula (I) in which ring A, R1,R2, R3, and n are as described herein. Also provided are dendron conjugates comprising the compounds, and methods of using the compounds, including a method of treating a disorder, such as inflammation, diabetes, insulin resistance, hyperglycemia, a lipid disorder, obesity, a condition associated with metabolic syndrome, and asthma, and a method of antagonizing P214 receptor activity in a cell.

Structure-Based Design of 3-(4-Aryl-1H-1,2,3-triazol-1-yl)-Biphenyl Derivatives as P2Y14 Receptor Antagonists

UDP and UDP-glucose activate the P2Y14 receptor (P2Y14R) to modulate processes related to inflammation, diabetes, and asthma. A computational pipeline suggested alternatives to naphthalene of a previously reported P2Y14R antagonist (3, PPTN) using docking and molecular dynamics simulations on a hP2Y14R homology model based on P2Y12R structures. By reevaluating the binding of 3 to P2Y14R computationally, two alternatives, i.e., alkynyl and triazolyl derivatives, were identified. Improved synthesis of fluorescent antagonist 4 enabled affinity quantification (IC50s, nM) using flow cytometry of P2Y14R-expressing CHO cells. p-F3C-phenyl-triazole 65 (32) was more potent than a corresponding alkyne 11. Thus, additional triazolyl derivatives were prepared, as guided by docking simulations, with nonpolar aryl substituents favored. Although triazoles were less potent than 3 (6), simpler synthesis facilitated further structural optimization. Additionally, relative P2Y14R affinities agreed with predicted binding of alkynyl and triazole analogues. These triazoles, designed through a structure-based approach, can be assessed in disease models.