In the field of early-stage Alzheimer's disease detection, research has increasingly focused on the development of diagnostic methods based on biological markers in more easily accessible body fluids, as an alternative to traditional detection in the brain. For the detection of such biomarkers in, for example, blood, the use of specific fluorescent molecular probes is also being investigated. The aim of this master’s thesis was the synthesis of a potential molecular probe, 3-acetyl-6-(6-((2-hydroxyethyl)(methyl)amino)naphthalen-2-yl)-2H-pyran-2-one. After the synthesis of the known enaminone 3-(dimethylamino)-1-(6-((2-hydroxyethyl)(methyl)amino) naphthalen-2-yl)prop-2-en-1-one, the focus was primarily on identifying a suitable protection group for the hydroxyl handle. For this purpose, the reagents di-tert-butyl dicarbonate, Me$_2$SO$_4$, dihydropyran, Me$_3$SiCl, and t-BuMe$_2$SiCl were tested. The latter proved to be the most suitable, yielding the stable protected compound containing the
t-BuMe$_2$Si– group. The protected enaminone was then converted to the desired O-protected pyranone via a two-step as well as a one-pot synthesis. In the final step, the protecting group was removed under acidic conditions, under which the pyranone ring remains stable. We performed measurements of the binding properties and optical properties of the final product.
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