本論文主要合成6-aminouridine 和6-(1,2,4-oxadiazol-3-yl)uridine 兩種類型的衍生物，作為具潛力的 orotidine 5’-monophosphate decarboxylase (ODCase) 的酵素抑制劑。
第一部分以6-cyano-1,3-dimethyluracil 作為反應模型，與一級胺試劑進行取代反應，可得到6-alkylamino-1,3-dimethyluracil 的產物，這個方法應用於6-cyanouridine 的衍生物上，同樣可藉由取代反應得到一系列6-alkylaminouridine 的衍生物。
第二部分將6-cyano-1,3-dimethyluracil 作為起始物與疊氮化鈉進行 click 合環反應，可得到6-(tetrazol-5-yl)-1,3-dimethyluracil，接著將此反應應用在6-cyanouridine 上，可以得到6-(tetrazol-5-yl)uridine 的產物。最後我們將六位腈基化合物與 hydroxylamine 反應形成 oxime，接著與苯環對位 (para) 具不同官能基的苯醯氯進行合環反應，可得到合環成為6-(5-phenyl-1,2,4-oxadiazol-3-yl)uridine 的衍生物。
這些六位具有取代基 uridine 衍生物，有潛力成為 ODCase 的抑制劑，未來將會進一步進行生物活性評估。

The focus of this thesis is the synthesis of derivatives for 6-aminouridine and 6-(1,2,4-oxadiazol-3-yl)uridine as a potential inhibitors for orotidine 5’-monophosphate decarboxylase (ODCase).

The 6-Cyano-1,3-dimethyluracil was chosen as the reaction model to investigate the substitution reaction with alkylamines as underwent nucleophiles. Our studies have shown that 6-cyano-1,3-dimethyluracil substitution reaction only with primary amines with primary alkyl substitutes. Finally, the reaction was applied for the synthesis of several 6-alkylaminouridine derivatives.

Furthermore, 6-Cyano-1,3-dimethyluracil as the starting material underwent click reaction with sodium azide to give 6-(tetrazol-5-yl)-1,3-dimethyluracil. The reaction was applied to prepare 6-(tetrazol-5-yl)uridine form 6-cyanouridine. Finally, the 6-cyanouridine derivatives was added hydroxylamine to give the corresponding oxime, and it was processed the cyclization reaction with the para-substituted benzoyl chlorides gave a series of 6-(5-phenyl-1,2,4-oxadiazol-3-yl)uridine derivatives
.
These 6-subsituted-uridine analogs are potential inhibitors for ODCase. Biological evaluation of the synthesized compounds will be investigated in the future.

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