Synthesis and characterization of CAPE derivatives as xanthine oxidase inhibitors with radical scavenging properties was written by Choi, Wonbeen;Villegas, Valente;Istre, Hannah;Heppler, Ben;Gonzalez, Niki;Brusman, Nicole;Snider, Lindsey;Hogle, Emily;Tucker, Janelle;Onate, Alma;Onate, Sandra;Ma, Lili;Paula, Stefan. And the article was included in Bioorganic Chemistry in 2019.Application of 2380-78-1 The following contents are mentioned in the article:
Inhibitors of the enzyme xanthine oxidase (XO) with radical scavenging properties hold promise as novel agents against reperfusion injuries after ischemic events. By suppressing the formation of damaging reactive oxygen species (ROS) by XO or scavenging ROS from other sources, these compounds may prevent a buildup of ROS in the aftermath of a heart attack or stroke. To combine these two properties in a single mol., we synthesized and characterized the non-purine XO inhibitor caffeic acid phenethylester (CAPE) and 19 derivatives using a convenient microwave-assisted Knoevenagel condensation protocol. Varying systematically the number and positions of the hydroxyl groups at the two Ph rings, we derived structure-activity relationships based on exptl. determined XO inhibition data. Mol. docking suggested that critical enzyme/inhibitor interactions involved π-π interactions between the phenolic inhibitor ring and Tyr914, hydrogen bonds between inhibitor hydroxyl groups and Glu802, and hydrophobic interactions between the CAPE Ph ring and non-polar residues located at the entrance of the binding site. To effectively scavenge the stable radical DPPH, two hydroxyl groups in 1,2- or 1,4-position at the Ph ring were required. Among all compounds tested, E-Ph 3-(3,4-dihydroxyphenyl)acrylate, a CAPE analog without the Et tether, showed the most promising properties. This study involved multiple reactions and reactants, such as 4-Hydroxy-3-methoxyphenethanol (cas: 2380-78-1Application of 2380-78-1).
4-Hydroxy-3-methoxyphenethanol (cas: 2380-78-1) belongs to ethers. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Application of 2380-78-1
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem