The Synthesis, Characterization And Properties Of Coumarin Glycosides And Coumarin-strapped Calixpyrrole Derivatives

Coumarin derivatives are one of the most important kinds of natural products, have a variety of biological activity. They are the main effective ingredients of natural medicines. What's more, because of their structural features, coumarin derivatives have excellent optical properties, such as fluorescent probe, fluorescence indicator and fluorescent dyes, coumarin derivatives played a very prominent role. Therefore, in order to research the both characteristics of coumarin derivatives and use the excellent molecular recognition effect of the calixpyrroles, this paper designed and synthesized coumarin-strapped calix[4]pyrrole derivatives. And, in order to further research medicinal characteristic of coumarin derivatives and increase coumarin derivatives water-solubility and drug targeting etc, this paper researched the methods of synthesization of coumarin glycosides derivatives.1. A series of coumarin-strapped calix[4]pyrrole derivatives were synthesized. With p-aminoacetophenone, acetone, new evaporate pyrrole as raw materials, HCl in synthesis process as catalyst, the compound 1 was synthesized; With 2-Hydroxy-1-naphthaldehyde, 4-(Diethylamino)salicylaldehyde, salicylaldehyde and diethyl malonate as raw materials, pyridine and acetic acid as catalysts, coumarin esters were synthesized, and through hydrolysis reaction, coumarin acid compounds were got. Using DCC/DMAP method and carbonyl chlorides method, coumarin-Strapped calix[4]pyrrole derivatives 2, 3, 4, 5 were synthesized. Compounds 1, 2, 3, 4 and 5 have been not reported in literatures.2. The fluorescence of the compounds 1, 2, 3, 4, and 5 of the complexation F- were tested. Through experiments we found out that F- anion have been recognised by compounds 1, 2, 5. The fluorescence of compound 1 appeared fluorescence enhancement with the concentration of F- increasing. And the fluorescence of compounds 2 and 5 appeared fluorescence weaken with the concentration of F- increasing.3. Three kinds of coumarins were synthesized. Using the two of them and trifluoroacetic acid as catalyst, coumarin-Strapped calix[2]pyrrole derivativers 6 and 7 were synthesized,which provided another kind of synthetic ways for the synthesization of calix[4]pyrroles. And they have been not reported in literatures.4. With two simple compounds for raw materials, using phase transfer catalyst method,Na₂CO₃ as catalyst,Coumarin glycosides compounds 8a-15a were synthesized. And compounds 8b-15b were got in the CH₃OH/CH₃ONa system. Compounds 8a, 8b, 10a, 10b, 15a and 15b are natural products whice have been first synthesized.5. All of the synthesized compounds have been confirmed by ¹H NMR, MS and IR.