新型水溶性C60脱氢枞胺吡咯烷衍生物的合成及抗HIV活性

doi:10.3969/j.issn.1000-2006.2013.02.026

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南京林业大学学报（自然科学版） ›› 2013, Vol. 37 ›› Issue (02): 147-150.doi: 10.3969/j.issn.1000-2006.2013.02.026

新型水溶性C₆₀脱氢枞胺吡咯烷衍生物的合成及抗HIV活性

胡军强,林中祥^*

南京林业大学化学工程学院,江苏南京 210037

出版日期:2013-04-18 发布日期:2013-04-18
基金资助:
收稿日期:2012-03-13 修回日期:2012-09-09
基金项目:国家自然科学基金项目(30871989,31170536); 江苏高校优势学科建设工程资助项目(PAPD)
第一作者:胡军强,硕士。*通信作者:林中祥,教授。E-mail: linzhongxiang36@gmail.com。
引文格式:胡军强,林中祥. 新型水溶性C₆₀脱氢枞胺吡咯烷衍生物的合成及抗HIV活性[J]. 南京林业大学学报:自然科学版,2013,37(2):147-

Synthesis and anti-HIV activity of a novel water-soluble C₆₀-dehydroabietylamine pyrrolidine derivative

HU Junqiang,LIN Zhongxiang^*

College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

Online:2013-04-18 Published:2013-04-18

摘要/Abstract

摘要： 将脱氢枞胺引入C₆₀分子中,设计合成了一种新型水溶性C₆₀脱氢枞胺吡咯烷型抗HIV(艾滋病毒)分子。以脱氢枞胺为原料,经过与乙二醛生成单希夫碱的反应引入醛基,用肌氨酸和C₆₀通过1,3-偶极环加成得到脱氢枞胺富勒烯衍生物,再将其进行羟基化,得到具有一定抗HIV活性的水溶性C₆₀脱氢枞胺富勒醇衍生物。利用IR、ESI-MS、¹H NMR、¹³C NMR、MALDI-TOF-MS,以及元素分析和热重分析等方法分析了新化合物及中间体的结构,结果表明,合成的C₆₀脱氢枞胺吡咯烷衍生物与理论结构相符。对最终产物进行了抗HIV活性测试,目标化合物具有一定的抗HIV-1逆转录酶活性,IC₅₀值为47.89 μg/mL。

Abstract: A novel water-soluble dehydroabietylamine fullerenol was synthesized and its anti-HIV activity had been evaluated. It was prepared by the hydroxylation of fulleropyrrolidine which was synthesized through the 1,3-dipolar cycloaddition of C₆₀, sarcosine and glyoxal dehydroabietylamine single Schiff base. The structures of all the compounds were characterized by IR, ESI-MS, MALDI-TOF-MS, ¹H NMR, ¹³C NMR, elemental analysis and TGA. The bioassay results showed that the synthesized dehydroabietylamine fullerend had great anti-HIV activity against HIV-1 reverse transcriptase in vitro and IC₅₀ was 47.89 μg/mL.

中图分类号:

TQ463.5

胡军强,林中祥. 新型水溶性C₆₀脱氢枞胺吡咯烷衍生物的合成及抗HIV活性[J]. 南京林业大学学报（自然科学版）, 2013, 37(02): 147-150.

HU Junqiang,LIN Zhongxiang. Synthesis and anti-HIV activity of a novel water-soluble C₆₀-dehydroabietylamine pyrrolidine derivative[J].Journal of Nanjing Forestry University (Natural Science Edition), 2013, 37(02): 147-150.DOI: 10.3969/j.issn.1000-2006.2013.02.026.

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新型水溶性C₆₀脱氢枞胺吡咯烷衍生物的合成及抗HIV活性

Synthesis and anti-HIV activity of a novel water-soluble C₆₀-dehydroabietylamine pyrrolidine derivative

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