Michael acceptor approach to the design of new salvinorin A-based high affinity ligands for the kappa-opioid receptor was written by Polepally, Prabhakar R.;Huben, Krzysztof;Vardy, Eyal;Setola, Vincent;Mosier, Philip D.;Roth, Bryan L.;Zjawiony, Jordan K.. And the article was included in European Journal of Medicinal Chemistry in 2014.Synthetic Route of C11H12O4 This article mentions the following:
The neoclerodane diterpenoid salvinorin A is a major secondary metabolite isolated from the psychoactive plant Salvia divinorum. Salvinorin A has been shown to have high affinity and selectivity for the κ-opioid receptor (KOR). To study the ligand-receptor interactions that occur between salvinorin A and the KOR, a new series of salvinorin A derivatives bearing potentially reactive Michael acceptor functional groups at C-2 was synthesized and used to probe the salvinorin A binding site. The κ-, δ-, and μ-opioid receptor (KOR, DOR and MOR, resp.) binding affinities and KOR efficacies were measured for the new compounds Although none showed wash-resistant irreversible binding, most of them showed high affinity for the KOR, and some exhibited dual affinity to KOR and MOR. Mol. modeling techniques based on the recently-determined crystal structure of the KOR combined with results from mutagenesis studies, competitive binding, functional assays and structure-activity relationships, and previous salvinorin A-KOR interaction models were used to identify putative interaction modes of the new compounds with the KOR and MOR. In the experiment, the researchers used many compounds, for example, 3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8Synthetic Route of C11H12O4).
3-(2,4-Dimethoxyphenyl)acrylic acid (cas: 6972-61-8) 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. But ether is more polar than alkenes. At room temperature, ethers are pleasant-smelling colourless liquids. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive, and as a result they are useful as solvents for fats, oils, waxes, perfumes, resins, dyes, gums, and hydrocarbons. Vapours of certain ethers are used as insecticides, miticides, and fumigants for soil.Synthetic Route of C11H12O4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem