2-吗啉基-1-丙基-1H-吲哚-3-取代酰腙类化合物的合成及抑菌活性  

Synthesis and Antibacterial Activity of 2-Morpholino-1-propyl-1H-indole-3-substituted Acylhydrazone Derivatives

作　　者：巫受群 李小琴 孟娇 甘宜远 田坤 王贞超[2,3] 欧阳贵平 Wu Shouqun;Li Xiaoqin;Meng Jiao;Gan Yiyuan;Wang Zhenchao;Ouyang Guiping(State Key Laboratory Breeding Base of Green Pesticide and Agrieultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research of Fine Chemicals, Guizhou University, Guiyang 550025;College of Pharmacy, Guizhou University, Guiyang 550025;Drug Synthetic Engineering Laboratory of Gu＆hou Province, Guizhou University, Guiyang 550025)

机构地区：[1]绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与生物工程重点实验室贵州大学精细化工研究开发中心,贵阳550025 [2]贵州大学药学院,贵阳550025 [3]贵州省合成药物工程实验室,贵阳550025

出　　处：《有机化学》2018年第6期1447-1453,共7页Chinese Journal of Organic Chemistry

基　　金：贵州省科技计划(No.20161055);贵州省大学生创新创业(No.201610657052);药用植物功效与利用国家重点实验室(No.201707)资助项目~~

摘　　要：以2-吲哚酮为先导化合物,设计合成一系列2-吗啉基-1-丙基-1H-吲哚-3-取代酰腙类化合物.目标化合物结构经核磁共振波谱(1H NMR和13C NMR)和高分辨质谱仪(HRMS)进行确证.采用浊度法测试了目标化合物的离体抑菌活性,抑菌活性测试结果表明:目标化合物对柑橘溃疡病菌(Xanthomonas axonopodis pv.Citri,X.citri)、烟草青枯病菌(Ralstonia.Solanacearum,R.solanacearum)和水稻白叶枯病菌(Xanthomonas oryzae pv.Oryzae,X.oryzae)均表现出一定的抑制活性.化合物2-氰基-N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)乙酰肼(12a)、4-氯-N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)苯甲酰肼(12c)、4-氟-N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)苯甲酰肼(12f)、N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)-4-硝基苯甲酰肼(12k)和N'-((2-吗啉基-1-丙基-1H-吲哚-3-基)亚甲基)异烟肼(12m)表现出较好的抑制活性;化合物12a、12c、12f、12k和12m对水稻白叶枯病菌的EC50为73.79、61.94、59.70、36.72和82.79μg/m L,抑制活性优于对照药叶枯唑和噻菌铜(EC50分别为92.4、120.22μg/m L).Berberine, honokiol, quercetin are the lead compounds with outstanding anti-tumor activities. Three novel products were synthesized from honokiol, quercetin and berberine. The structures of the products were firstly confirmed by 1 H NMR, 13 C NMR, 2 D NMR, HRMS, IR and UV. All products were evaluated for their anti-tumor activities against Hep G2 cell in vitro and the results showed that the inhibitory effects of two compounds on Hep G2 cell were far superior to honokiol and berberine hydrochloride, and the anti-tumor activities were similar to the reference drug cisplatin. It means that compounds 1 and 2 are expected to be the potential anti-tumor drugs.

关 键 词：吲哚衍生物 酰腙 酰肼 抑菌活性 

分 类 号：O626[理学—有机化学] TQ455[理学—化学]