| Design and Synthesis of Glycosylated Aromatic Nitrogen Mustard Derivatives |
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| 引用本文： | LIU Tie-mei WANG Shu-sheng ZHU Guang-ze LI Ming-yang ZHANG Li-ping. Design and Synthesis of Glycosylated Aromatic Nitrogen Mustard Derivatives[J]. 高等学校化学研究, 2007, 23(3): 300-302. DOI: 10.1016/S1005-9040(07)60064-6 |
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| 作者姓名： | LIU Tie-mei WANG Shu-sheng ZHU Guang-ze LI Ming-yang ZHANG Li-ping |
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| 作者单位： | LIU Tie-mei1，2，WANG Shu-sheng3，ZHU Guang-ze4，LI Ming-yang2 and ZHANG Li-ping11. School of Life Sciences，Northeast Normal University，Changchun 130024，P. R. China;2. China-Japan Union Hospital，Jilin Universty，Changchun 130033，P. R. China;3. School of Life Science，Anhui University，Hefei 230039，P. R. China;4. College of Traditional Chingese Medicine in Changchun，Changchun 130021，P. R. China |
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| 基金项目： | 国家自然科学基金，吉林省教育厅自然科学基金 |
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| 摘 要： | Antibody-directed enzyme prodrug therapy(ADEPT) is a new strategy for the treatment of cancer that has arisen in recent twenty years, the main merits of which are that it can improve the selectivity of anticancer drugs and reduce the side effects in remote tissue. In the present study, two prodrugs-glycosylated aromatic nitrogen mustard derivatives were synthesized. Glucose and lactose were converted into glycosyl donors-trichloroacetimidate; the obtained glycosyl donors were glycosylated with p-nitrophenol(glycosyl donors) to form β-glucosyl p-nitrobenzene and β-lactosyl p-nitrobenzene that were protected by acetyl in a stereoselective manner; the two products were reduced by zinc dust and then treated with ethylene oxide, afforded two glycosylated nitrogen mustard derivatives that were protected by acetyl; the last step was to deacetylate and then afforded the two target compounds that could be used as prodrugs of ADEPT for further Anti-tumor research.
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| 关 键 词： | 糖基化 芳香族氮芥衍生物 设计 合成 ADEPT 抗癌药 |
| 收稿时间： | 2006-12-22 |
| 修稿时间： | 2006-12-22 |
Design and Synthesis of Glycosylated Aromatic Nitrogen Mustard Derivatives |
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| Tie-mei LIU, Shu-sheng WANG, Guang-ze ZHU, Ming-yang LI,Li-ping ZHANG,. Design and Synthesis of Glycosylated Aromatic Nitrogen Mustard Derivatives[J]. Chemical Research in Chinese University, 2007, 23(3): 300-302. DOI: 10.1016/S1005-9040(07)60064-6 |
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| Authors: | Tie-mei LIU Shu-sheng WANG Guang-ze ZHU Ming-yang LI Li-ping ZHANG |
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| Affiliation: | aSchool of Life Sciences, Northeast Normal University, Changchun 130024, P. R. China;bChina-Japan Union Hospital, Jilin Universty, Changchun 130033, P. R. China;cSchool of Life Science, Anhui University, Hefei 230039, P. R. China;dCollege of Traditional Chinnese Medicine in Changchun, Changchun 130021, P. R. China |
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| Abstract: | Antibody-directed enzyme prodrug therapy(ADEPT) is a new strategy for the treatment of cancer that has arisen in recent twenty years, the main merits of which are that it can improve the selectivity of anticancer drugs and reduce the side effects in remote tissue. In the present study, two prodrugs-glycosylated aromatic nitrogen mustard derivatives were synthesized. Glucose and lactose were converted into glycosyl donors-trichloroacetimidate; the obtained glycosyl donors were glycosylated with p-nitrophenol(glycosyl donors) to form β-glucosyl p-nitrobenzene and β-lactosyl p-nitrobenzene that were protected by acetyl in a stereoselective manner; the two products were reduced by zinc dust and then treated with ethylene oxide, afforded two glycosylated nitrogen mustard derivatives that were protected by acetyl; the last step was to deacetylate and then afforded the two target compounds that could be used as prodrugs of ADEPT for further Anti-tumor research. |
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| Keywords: | Glycosylation Nitrogen mustard derivative Prodrug ADEPT |
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