| Summary: | 碩士 === 東海大學 === 化學系 === 102 === Part I、Design and synthesis of potential histone deacetylase inhibitors
This part of the thesis mainly described the design and attempted synthesis of the histone deacetylase inhibitors. First, we tried to react methyl 4-(3-hydroxyprop-1-yn-1-yl)-2-methoxybenzoate with tryptamine via a nucleophilic substitution reaction, but the yield was very low. Alternately, we tried to couple methyl 4-iodo-2-methoxybenzoate with propargyl bromide or allyl bromide using Sonogashira or Heck reaction, no desired products were obtained. Second, we switched the order of the synthesis by first coupling of tryptamine with propargyl bromide or allyl bromide, and followed by reacting of the resulting product with methyl p-iodobenzoate via Sonogashira or Heck reaction. Once again, this synthetic attempt remained futile. Finally, we first protected the amine group of tryptamine with tosyl chloride. The tosyl-protected tryptamine was then reacted with propargyl bromide or allyl bromide. The resulting product was subsequently coupled with methyl 4-iodobenzoate to give the desired product successfully. Unfortunately, even various deprotection methods have been employed, the tosylate group cannot be removed from the product.
Part II、Light-mediated synthesis of indazolo[3,2-b]quinazolines and their properties
This part of the thesis mainly described the facile synthesis of indazolo[3,2-b]quinazolines by exposing readily available 2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinazolines to the UV light in acetonitrile. The scope and limitation of this light-mediated reaction and the redox-switching properties of the prepared compounds were explored. Our studies suggest that the conformation of the amine moiety and o-nitrophenyl group plays a critical role in this photochemical reaction. Further, introducing an electron-withdrawing group such as carbonyl group on the amine moiety will diminish the resulting compound's sensitivity toward the photoreaction. Moreover, the prepared indazolo[3,2-b]quinazolines were found to possess reversible redox-switching properties with color change and emission variation as two output properties.
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