於本篇論文中, 本人發展一個製備內醯亞胺衍生物作為新型光引導去氧核醣核酸交聯試劑的路徑。另外，本人亦探討利用紫外光照射圬酯化合物之方式對去氧核醣核酸造成雙股切割之效果。除此之外，本人也製備一系列苯并咪唑類化合物並檢測該類化合物對於C型肝炎病毒之抑制活性。
在本論文的第一部分，本人合成三個新型光引導去氧核醣核酸交聯試劑。藉由紫外光（波長312 nm）照射，磷酸緩衝溶液中之去氧核醣核酸交結試劑與pBR322去氧核醣核酸會生成交聯之構造。
在第二部分中，本人以間位或對位取代之苯甲醯氯與七種嵌入體化合物進行縮合反應，建立一個含有六十三個圬酯化合物的資料庫。在含氧的條件下以紫外光（波長312 nm）照射兩小時後，磷酸緩衝溶液中之圬酯化合物與φX174 RFI去氧核醣核酸會產生單股切割之效果。從控制實驗的結果指出，紫外光在去氧核醣核酸切割過程中扮演"板機"的角色。
在第三部分中，採用香豆素與苯并咪唑作為起始物，經由“一爐法”反應得到二十四個不同之新苯并咪唑類化合物。其中，硫甲基被用來連接這兩類化合物，進而建立結構活性關聯。從抑制C型肝炎表現的實驗數據及結構活性關聯分析指出，主要的活性來自於香豆素及其六號碳位置上的溴取代基。

In this thesis, I developed a synthetic route for the preparation of phthalimide derivatives as novel photo-induced DNA cross-linking agents. I also explored the DNA cleaving ability of oxime esters, which can perform double-strand scission upon UV irradiation. Furthermore, a series of benzimidazoles were prepared and screened their inhibitions against HCV.
In part 1 of this thesis, three new photo-induced DNA cross-linking agents were synthesized. Irradiation with UV light (312 nm) of these cross-linking agents in a phosphate buffer containing the linearized pBR322 DNA afforded the DNA cross-links.
In part 2, a compound library containing 63 O-benzoyl oxime esters was set up from condensation of meta- or para-substituted benzoyl, 1-naphthoyl or 2-naphthoyl chlorides with oximes of seven different kinds of intercalators. Irradiation with UV light (312 nm) of these oxime esters containing the supercoiled circular φX174 RFI DNA under aerobic conditions for 2.0 h resulted in the single-strand scission of DNA. Results from control experiments indicate that UV light functioned as a "trigger" to initiate the DNA cleavage processes.
In part 3, totally 24 new conjugated compounds were successfully synthesized by a one-flask method from benzimidazole and courmarine derivatives. A methylthio linker was used to connect these two classes of compounds, onto which were attached with various substituents for establishment of the structure¬–activity relationship. Structural-activity relationships from the HCV inhibition activity indicated the –CH2–coumarine moiety with Br substituent at the C-6’ position was essential for the enhancement of selectivity.

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