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  • 郭俊香,梁萌,张春梅,王亮,胡宏岗.新型苦参碱衍生物的设计合成及其体外抗炎活性[J].第二军医大学学报,2011,32(11):1223-1226    [点击复制]
  • GUO Jun-xiang,LIANG Meng,ZHANG Chun-mei,WANG Liang,HU Hong-gang.Synthesis of novel matrine derivatives and their in vitro anti-inflammatory activity[J].Acad J Sec Mil Med Univ,2011,32(11):1223-1226   [点击复制]
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新型苦参碱衍生物的设计合成及其体外抗炎活性
郭俊香1,梁萌1,张春梅1,王亮1,2,胡宏岗1*
0
(1. 第二军医大学药学院有机化学教研室,上海 200433;
2. 烟台大学药学院药物化学教研室,烟台 264005
*通信作者)
摘要:
目的 设计合成新型苦参碱衍生物,并研究其体外抗炎活性。 方法 以槐果碱为起始原料,经硫代和经典的Michael加成反应得到10个目标化合物;所得化合物均考察了其体外对抗炎因子TNF-α释放以及NF-κB转染的影响。 结果 合成的目标化合物经1HNMR和ESI-MS确证其结构。所得化合物体外对TNF-α的释放和NF-κB转染均具有一定的抑制作用,其中化合物 1f 对TNF-α的释放抑制作用最强,IC50为9.4 μmol/L。 结论 苦参碱的13位引入小的直链氨基侧链能够增强其抗炎活性。
关键词:  苦参碱  衍生物  肿瘤坏死因子α  NF-κB
DOI:10.3724/SP.J.1008.2011.01223
投稿时间:2011-04-13修订日期:2011-06-25
基金项目:国家自然科学基金(20902109).
Synthesis of novel matrine derivatives and their in vitro anti-inflammatory activity
GUO Jun-xiang1,LIANG Meng1,ZHANG Chun-mei1,WANG Liang1,2,HU Hong-gang1*
(1. Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China;
2. Department of Medicinal Chemistry, School of Pharmacy, Yantai University, Yantai 264005, Shandong, China
*Corresponding author.)
Abstract:
Objective To design and synthesize a series of novel matrine derivatives and to investigate their in vitro anti-inflammation activities. Methods Ten novel matrine analogues were synthesized via thiosulfate reaction and classical Michael addition using sophocarpine as the starting material. The effects of all the analogues on TNF-α production and NF-κB transcriptional activity were evaluated in vitro. Results The synthesized compounds were confirmed correct by 1HNMR and ESI-MS. Biological studies showed that the synthetic derivatives had inhibitory effects against TNF-α production and NF-κB transcriptional activity. Compound 1f had the strongest inhibitory effect against TNF-α production, with an IC50 value of 9.4 μmol/L. Conclusion Introduction of liner small substitutes at the 13-position of matrine can enhance its anti-inflammatory activity.
Key words:  matrine  derivatives  tumor necrosis factor-α  NF-κB