取代苯甲醛缩氨基硫脲(脲、硝基胍)类化合物的合成及其对小菜蛾酪氨酸酶的抑制活性

酪氨酸酶是昆虫生长发育过程中的一个关键性酶,控制酪氨酸酶的活性即可调节昆虫的生长行为。以苯甲醛缩氨基硫脲为母体化合物,通过变换硫脲结构片段,设计了18个结构类似的苯甲醛缩氨基硫脲(脲、硝基胍)类化合物,以取代苯甲醛、氨基硫脲、水合肼等为原料经1~2步反应合成了目标化合物,其结构通过红外、核磁共振氢谱、质谱(ESI)表征。生物活性测试结果表明,硫脲类化合物对小菜蛾酪氨酸酶的抑制活性明显高于脲(硝基胍)类化合物,说明硫脲结构的存在对化合物的活性有利。

Synthesis of substituted benzylidene hydrazinecarbothioamide (hydrazinecarboxamide,nitrohydrazinecarboximidamide) and their inhibitory activity on tyrosinase of diamondback moth Plutella xylostella (L.)

Tyrosinase is a key enzyme in the growth and development of insect.The development of insect can be affected by regulating its tyrosinase activity.Eighteen substituted benzylidene hydrazinecarbothioamide (hydrazinecarboxamide,nitrohydrazinecarboximidamide) compounds were designed based on changing the thiourea structure fragment of parent compound benzylidene hydrazinecarbothioamide.The title compounds were synthesized from the starting materials of substituted benzaldehyde,thiosemicarbazide,hydrazine hydrate,etc.in 1 - 2 steps and their structures were characterized by IR,¹H NMR and MS (ESI).Their effects on tyrosinase of the diamondback moth Plutella xylostella (L.) were tested.The bioassay results showed that compounds containing thiourea behaved higher inhibitory activity than compounds containing urea (nitro guanidine),which implied that thiourea fragment was favorable to the activity of compounds.