Biological evaluation of pyridone alkaloids on the endocannabinoid system was written by Chicca, Andrea;Berg, Regina;Jessen, Henning J.;Marck, Nicolas;Schmid, Fabian;Burch, Patrick;Gertsch, Jurg;Gademann, Karl. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Formula: C14H15BO4 This article mentions the following:
Naturally occurring pyridone alkaloids as well as synthetic derivatives were previously shown to induce neurite outgrowth. However, the mol. basis for this biol. effect remains poorly understood. In this work, the authors have prepared new pyridones, and tested the effect of thirteen 4-hydroxy-2-pyridone derivatives on the components of the endocannabinoid system. Investigation of binding affinities towards CB1 and CB2 receptors led to the identification of a compound binding selectively to CB1鑱?strong>I. Compound I and a closely related derivative also inhibited anandamide (AEA) hydrolysis by fatty acid amide hydrolase. Interestingly, none of the compounds tested showed any effect on 2-AG hydrolysis by monoacylglycerol lipase at 10 娓璏. Assessment of AEA uptake did, however, lead to the identification of four inhibitors with IC50 values in the submicromolar range and high selectivity over the other components of the endocannabinoid system. In the experiment, the researchers used many compounds, for example, (4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4Formula: C14H15BO4).
(4-((4-Methoxybenzyl)oxy)phenyl)boronic acid (cas: 156635-90-4) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethers feature bent C閳ユ彊閳ユ弲 linkages. In dimethyl ether, the bond angle is 111鎺?and C閳ユ彊 distances are 141 pm. The barrier to rotation about the C閳ユ彊 bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.Formula: C14H15BO4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem