| 5-氟尿嘧啶-1-基磷三肽化合物的合成及抗癌活性研究 |
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| 引用本文： | 刘学军,陈茹玉,杨媛媛. 5-氟尿嘧啶-1-基磷三肽化合物的合成及抗癌活性研究[J]. 高等学校化学学报, 2002, 23(7): 1299-1303 |
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| 作者姓名： | 刘学军 陈茹玉 杨媛媛 |
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| 作者单位： | 1. 天津大学化工学院, 天津 300072;2. 南开大学元素有机化学研究所, 元素有机化学国家重点实验室, 天津 300071;3. 天津药业有限公司博士后工作站, 天津 300161 |
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| 基金项目： | 国家自然科学基金 (批准号 :2 9972 0 2 1) |
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| 摘 要： | 以DCC(二环己基碳二酰亚胺)/BtOH(1-羟基苯并三氮唑)为偶联剂,通过液相偶联法合成了14个新型5-氟尿嘧啶-1-基磷三肽化合物,收率为52%～83%.所有化合物经1HNMR,31PNMR,IR光谱和元素分析证实.提出了合成中间体5-氟尿嘧啶-1-基乙酸的方法,其优点是操作简便且产率高.对部分化合物进行了抗癌活性测试,结果表明该类化合物对HL-60和BEL740癌细胞生长具有一定的抑制作用.
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| 关 键 词： | 5-氟尿嘧啶 肽偶联法 磷三肽 抗癌活性 |
| 文章编号： | 0251-0790(2002)07-1299-05 |
| 收稿时间： | 2001-04-11 |
Synthesis and Anticancer Activities of Novel 5-Fluorouracil-1-yl Phosphonotripeptides |
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| LIU Xue-Jun,CHEN Ru-Yu,YANG Yuan-Yuan. Synthesis and Anticancer Activities of Novel 5-Fluorouracil-1-yl Phosphonotripeptides[J]. Chemical Research In Chinese Universities, 2002, 23(7): 1299-1303 |
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| Authors: | LIU Xue-Jun CHEN Ru-Yu YANG Yuan-Yuan |
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| Affiliation: | 1. School of Chemical Engineering, Tianjin University, Tianjin 300072;2. Institute and National Key Laboratory of Elemento Organic Chemistry, Nankai University, Tianjin 300071;3. Base for Postdoctoral Scientific Researching of Tianjin Pharmaceutical Incor.Ltd.Tianjin 300161, China |
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| Abstract: | Aseries of novel 5-fluorouracil-1-yl phosphonotripetides were synthesized in yield 52%-83% by peptide coupling reaction with DCC/BtOH as the activiating carboxyl group reagent. All products were characterized by 1H NMR, 31P NMR, IRspectra and elemental analyses. The facile method was used to synthesize 5-fluorouracil-1-yl acetic acid(an important intermediate). It was found that two main factors affected the conversion of[(5-fluorouracil-1-yl)methylformyl]aminomethylformic acid to the title compounds. One is the apparent steric hindrance of an α aryl group having a bulky substituent at the ortho position. Another is the electronic effect of the substituent of the α aryl groups. The electron withdrawing groups decrease the nucleophilicity of the amino group. The yields of all products containing the strong electron withdrawing groups were lower than those of other products. The in vitro antitumor activity test showed that some of the synthesized compounds are the potential anticancer agent. |
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| Keywords: | Fluorouracil Peptide coupling Phosphonotripeptides Anticancer activity |
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