Synthesis of fluorescent molecules for the detection of nerve agents and synthesis of novel pyrazolo and isoxazolo quinoline derivatives as potential drugs

The main focus of chapters I and II of this dissertation is the synthesis and characterization of novel materials that will have high specificity and sensitivity for the detection of highly toxic organophosphate and organophosphonate nerve agents. The study was divided into two main sections, synthesis of quinolinone and 4-aminonaphthalimide derivatives, and binding studies of synthesized target molecules with nerve agent mimics, DCP and DFP. Nine quinolinone target molecules (TR-1, TR-2, TR-3, TR-4, TR-5, 8, 32, 9, and 10) were synthesized, and binding studies of these molecules with nerve agent mimic were also carried out. All the molecules containing the Schiff base moiety (e.g. TR-1, TR-2, TR-3 and TR4) undergo protonation upon attempted reaction with DCP. On the other hand, 7-dimethylamino-4-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde oxime (8) react with nerve agent mimic DCP during reaction studies. Three molecules containing functionalized tethers (TR-4S, TR-5S, and TR-1C) were synthesized so that they can bind to anodic aluminum oxide (AAO) with the help of covalent bonds in order to fabricate sensors for nerve agents. Two 4-aminonaphthalimide dyes, the lithium salt of lucifer yellow (38) and the potassium salt of lucifer yellow 43, were also synthesized successfully. Reactions of nerve agent mimic DCP with AAO which had been impregnated with 38 were studied by fluorescence spectroscopy. Twenty-seven other novel compounds, beside target molecules, were generated in the process of synthesizing quinolinone and 4-aminonaphthalimide target molecules. Chapter III of this dissertation deals with the synthesis of novel pyrazolo and isoxazolo quinoline derivatives as potential medicinal agents. Four pyrazolo and isoxazolo quinoline derivatives (51, 53, 54 and 55) were synthesized and are yet to be tested for the antiviral activity. Nine novel compounds were generated in the synthetic routes described in this chapter.