| Summary: | 碩士 === 臺北醫學大學 === 藥學系 === 92 === Mylabris phalerata, Meloidae family of Coleoptera, has been known since antiquity to produce a potent toxic defensive agent, now known as cantharidin (exo,exo-2,3-dimethyl-7-oxabicyclo [2.2.1] heptane-2,3- dicarboxylic anhydride), but more infamously known as Spanish Fly. In the past, Cantharidin has used as anticancer, herbicidal, pesticide and treatment of molluscum contagiosum activities.
The new analogues contain various amino acids attached to the carboxylic anhydride exhibit antibacterial activity. The compounds with triazole structure have been evaluated their antitubercular activity and the new adamantanyl derivatives have found to have antibacterial activity. In addition, some new 1,3,4-thiadiazoles containing isomeric pyridyl have been found to be active against both Gram-positive and Gram-negative bacteria.
We used cantharidin as a starting material to react with primary amine, series of amino acid, diaminotriazole and aminoadamantane, by heating 200℃ in sealed tube to form various cantharidinimide derivatives. Furthermore, we used anhydrides and aminothiadiazole in the same condition to obtain thiazolylimide derivatives.
We suppose that it might have some steric hindrance between bulky amino acids and 2,3-dimethyl group of cantharidin and gave low yields. And we found that higher polarity of amino acids didn’t react with cantharidin.
All of the cantharidinimide and thiazolylimide derivatives were measured by 1H-NMR, IR and mass spectrometry. Therefore, we would try to evaluate antibacterial activity of cantharidinimide and thiazolylimide derivatives. The results indicated that compound 13 (4-Anthracen-2-yl-2,6-dimethyl-10-oxa-4-aza-tricyclo[5.2.1.02,6]decane-3,5-dione) exhibits higher inhibitory activity against Staphylococcus and Bacillus than others, but is still less effective than penicillin G.
|
|---|
