為顯影疱疹病毒之胸腺苷激酶，5-取代基之阿拉伯醣化尿苷類似物的合成，是十分吸引人的。經由產率77% 的2,2'-環化尿苷及其開環、產率99% 之去有機錫的5-碘-125化…等等反應，可製備「5-碘-125化阿拉伯醣化尿苷類似物」。其中，可用「雙三苯基膦二氯化鈀」催化「六甲基二錫」的5-去碘有機錫化反應，製成產率75% 的 「2',3',5'-乙醯酯保護N1-阿拉伯苷之5-三甲基有機錫化尿嘧啶」。以市售選擇氟試劑的去有機錫之鹵化反應，製成非放射性氟化的目標化合物，例如，產率28% 的「5-氟化阿拉伯醣化尿苷類似物」和產率7% 的「5-(氟化乙烯)阿拉伯醣化尿苷類似物」。
我們採用平行液相合成的策略，實現發展癌症化學治療和腫瘤造影劑的另一研究目標。我們以「苯並三氮唑-N,N,N',N'-四甲基脲六氟磷酸酯」催化正丁基醯胺鍵形成，以「四甲基偶氮唑鹽」，進行抑制腫瘤細胞生長篩選：結果意外發現，利尿酸和芬布芬兩個常用藥物衍生之正丁基醯胺，具有抑制人類非小細胞肺癌和表皮乳癌細胞的生物活性。為製備放射性氟取代化合物，需要先製備甲苯磺醯化的前驅物；以「叔丁基甲酸醯胺-4-氫氧基-正丁基利尿醯胺」和「甲苯磺醯氯」，產生產率20% 的甲苯磺醯前驅物。此外，可從上述醇，製備產率45% 的「叔丁基甲酸醯胺-4-氟化-正丁基利尿醯胺」，作為可靠的標準品。依序使用「氯化叔丁基二甲基矽」、「雙叔丁基碳酸酐」和「氟化四丁基銨」的三步驟反應，達成產率40% 的取代質子以保護醯胺鍵；在放射性親核氟化時，避免環化反應發生。
以氯化試劑，作「1,8-正辛雙醇」的雙甲苯磺醯化合物；接著是作甲苯磺醯化離去基的疊氮轉移及親核性氟化取代另一離去基，三步驟產出28% 的非放射性「8-氟化正辛疊氮」。又以「三苯基膦」氫化「8-氟化正辛疊氮」，製備產率58% 的產物─非放射性「8-氟化正辛胺」。另一個「1-胺基-1-去氧植物鞘胺醇」的醯胺分子庫，亦用「四甲基偶氮唑鹽」試劑，篩選細胞生長活性，為達成自然殺手T細胞生長的目標。

For imaging herpes simplex virus thymidine kinase, syntheses of 5-substituted arabinosyl uridine analogs were highly desirable. 5-[125I]Iodo arabinosyl uridine analog was prepared from 2,2'-cyclouridine via ring opening and destannyl radioiodination in 77% yield and in 99% yield respectively. 2',3',5'-O-acetyl N1-arabinosyl 5-trimethylstannyl uracil was prepared via deiodostannylation using hexamethylditin under catalysis of bis(triphenylphosphine)palladium dichloride in 75% yield. Cold target compounds, eg. 5-fluoro and (E)-5-(2-fluorovinyl) arabinosyl uridine analogs, were prepared via halodestannylation with selectfluorTM in 28% and 7% yield, respectively.
Our other research goal regarding the development of cancer chemotherapy and tumor imaging agents has been realized through parallel solution-phase synthesis approach. We constructed a library of n-butyl amides under HBTU catalysis followed by 3-(4,5-cimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) screening. Unexpectedly, n-butyl amides of two common pharmaceuticals: ethacrynic acid and fenbufen revealed substantial toxicities against both A549 and MCF7 cell lines. For preparing radiofluoro substituted compounds, the required precursor, a tosylate, needed to be prepared first. N-Boc-4-hydroxy-n-butyl ethacrynic amide was used to generate the tosylate with TsCl in 20% yield. In addition, the authentic standard, N-Boc-4-fluoro-n-butyl ethacrynic amide, was prepared from the alcohol in 45% yield. For preventing the ring closure during radionucleophilic fluorination, the proton of amido group should be protected via three steps of reactions in 40% yield via t-butyldimethylsilyl chloride, di(t-butyl carbonate) anhydride and tetrabutylammonium fluoride/AcOH, sequentially.
8-Fluoro-n-octyl azide was prepared via di-tosylation of 1,8-n-octan-diol with TsCl, followed by azide-transfer reaction and nucleophilic fluoro substitution. The yield via three steps was 28%. Followed by hydrogenation with triphenylphosphine, the desired core amino compound, 8-fluoro-n-octyl amine, was obtained in 58% yield. Another library of 1-amino-1-deoxy phytosphingosine analogs for targeting nature killer T cell proliferation was screened for their anti-cellular growth activity with MTT assay as well.

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