New high affinity H3 receptor agonists without a basic side chain was written by Kitbunnadaj, Ruengwit;Hoffmann, Marcel;Fratantoni, Silvina A.;Bongers, Gerold;Bakker, Remko A.;Wieland, Kerstin;el Jilali, Ahmed;De Esch, Iwan J. P.;Menge, Wiro M. P. B.;Timmerman, Henk;Leurs, Rob. And the article was included in Bioorganic & Medicinal Chemistry in 2005.Synthetic Route of C9H16O3 This article mentions the following:
In this study, we replaced the basic amine function of the known histamine H3 receptor agonists imbutamine or immepip with non-basic alc. or hydrocarbon moieties. All compounds in this study show a moderate to high affinity for the cloned human H3 receptor and, unexpectedly, almost all of them act as potent agonists. Moreover, in the alc. series, we consistently observed an increased selectivity for the human H3 receptor over the human H4 receptor, but none of the compounds in this series possess increased affinity and functional activity compared to their alkylamine congeners. In this new series of compounds VUF5657, 5-(1H-imidazol-4-yl)-pentan-1-ol, is the most potent histamine H3 receptor agonist (pKi = 8.0 and pEC50 = 8.1) with a 320-fold selectivity at the human H3 receptor over the human H4 receptor. In the experiment, the researchers used many compounds, for example, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2Synthetic Route of C9H16O3).
Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (cas: 103260-44-2) belongs to tetrahydropyran derivatives. Tetrahydropyrans are also used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. There is large number of marine macrolide natural products that contain tetrahydropyran and tetrahydrofuran ring together. For instance, goniodomin A (actin targeting polyether), prorocentrolide (toxin halistatins), and percentotoxineSynthetic Route of C9H16O3
Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics