7-(1-酰基哌嗪-4-基)甲基喜树碱衍生物的合成及杀虫活性

Synthesis and insecticidal activity of 7-(l-carbonyl-piperazin-4-yl)methyl-camptothecin derivatives

以(20S)-喜树碱(CPT)为原料,根据类同合成法和亚结构连接法原理,对CPT的7-C位进行修饰,得到了系列新型7-(1-酰基哌嗪-4-基)甲基喜树碱衍生物(4a^4m),所有衍生物的结构均通过核磁共振氢谱(1H NM R)和液-质联用(LC-M S)等方法确证;并初步测定了其对朱砂叶螨Tetranychus cinnabarinus和松材线虫Bursaphelenchu xylophilus的室内杀虫活性。结果表明:与喜树碱相比,各衍生物均表现出不同程度的杀虫活性,其中化合物7-[1-(4-甲氧基苯酰基)哌嗪-4-基]-甲基喜树碱(4g)和7-(1-环戊酰基哌嗪-4-基)-甲基喜树碱(4j)对朱砂叶螨24 h的半数致死浓度(LC50值)分别为8.10和9.05 mg/L,对松材线虫的LC50值分别为6.34和6.68 mg/L。研究结果可为喜树碱衍生物杀虫活性构效关系研究奠定基础。

With （20S）-camptothecin （CPT） as the raw material, a series of 7-（1-carbonyl-piperazin-4-yl） methyl-camptothecin derivatives （4a-4m） were synthesized after modification of C7 of CPT. Their structures were identified by1 H NMR and LC-MS. The preliminary bioassay showed that the compound 7-（ 1-（ 4-methoxybenzoyl ） piperazin-4-yl ） methyl-camptothecin （ 4 g ） and 7-（ 1-cyclopentanecarbonyl-piperazin-4-yl ） methyl-camptothecin （ 4 j ） exhibited more insecticidal activity against Tetranychus cinnabarinus and Bursaphelenchu xylophilus than CPT. For T. cinnabarinus, LC50 value （24 h） of 4g was 8. 10 and 9. 05 mg/L. And for B. Xylophilus, LC50 （24 h） value of 4j was 6. 34 and 6. 68 mg/L. The results are useful for the investigation of insecticidal activity and structure-activity relationship of camptothecin derivatives.