14-羟基菲并[9,10,3',4']吲哚里西啶的合成及生物活性研究  

Synthesis of 14-Hydroxyphenanthro[9,10,3',4']indolizidine and Its Biological Activities

作　　者：王开亮[1] 汪清民[1] 黄润秋[1] 

机构地区：[1]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

出　　处：《有机化学》2008年第10期1826-1829,共4页Chinese Journal of Organic Chemistry

基　　金：国家重点基础研究发展规划(No.2003CB114404);国家自然科学基金(No.20872072);教育部科学技术研究重点(No.106046)资助项目.

摘　　要：以吡咯为起始原料,以三氟氧钒(VOF3)氧化偶联重排反应为关键步骤,经过7步反应,合成了结构骨架全新的14-羟基菲并[9,10,3',4']吲哚里西啶化合物8,总收率为55%.采用1HNMR,13CNMR,IR,MS和HRMS对中间体和目标产物进行了表征.初步的抗烟草花叶病毒生物活性测试结果表明,目标化合物8对烟草花叶病毒无明显抑制作用,但具有较好的抗肿瘤活性,中间体9-氧代-14-羟基-14a-甲氧基菲并[9,10,3',4']吲哚里西啶化合物7却表现出了很好的抗烟草花叶病毒活性.A new compound, 14-hydroxyphenanthro[9,10,3＇,4＇]indolizidine （8）, has been synthesized util- izing pyrrole as starting material via the oxidative coupling and rearrangement reactions by vanadium oxy- trifluoride （VOF3） in seven steps in an overall yield 55%. The structures of the target compound and its precursors were confirmed by 1H NMR, 13C NMR, IR, MS and HRMS techniques. Preliminary bioassay showed that 8 had weak antiviral activity against tobacco mosic virus （TMV）, but exhibited potential anti- tumour activity. The intermediate 9-oxo-14-hydroxy-14a-methoxyphenanthro[9,10,3＇,4＇]indolizidine （7） exhibited excellent antiviral activity against TMV.

关 键 词：三氟氧钒 菲并吲哚里西啶 烟草花叶病毒 抗肿瘤活性 

分 类 号：O626[理学—有机化学]