含4-正庚/正辛氧基苯基杂环化合物的设计、合成及生物活性

王宝雷; 马瑞典; 赵卫光; 李正名; 李永红

含4-正庚/正辛氧基苯基杂环化合物的设计、合成及生物活性

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

基金项目:

国家重点基础研究发展计划("973"计划)项目(2003CB114406);高等学校博士学科点专项科研基金(20070055044);天津市应用基础及前沿技术研究计划(08JCYBJC00800)资助.

计量
- 文章访问数: 1112
- HTML全文浏览量: 37
- PDF下载量: 365
- 被引次数: 0
出版历程
- 收稿日期: 2008-12-10

Design,Synthesis and Biological Activity of Heterocyclic CompoundsContaining 4-(Heptyloxy/octyloxy)phenyl Group

1.
Elemento-organic Chemistry Institute,The State Key Laboratory of Elemento-organic Chemistry,Nankai University, Tianjin 300071,China

摘要

摘要: 通过研究苯甲脒类抑制剂与酮醇酸还原异构酶(KARI)对接的结合模式,设计合成了一系列含正庚氧基及正辛氧基苯基的杂环化合物。用核磁共振氢谱、红外光谱、质谱及元素分析对26个目标产物(其中22个是新化合物)的结构进行了表征和确认。初步生物活性测试结果表明,目标化合物大多具有不同程度的水稻KARI酶抑制活性和除草活性,其中化合物 9a和9b 在200 μg/mL浓度下对KARI酶的抑制率分别为65.7%和71.1%,在100 μg/mL浓度下对双子叶植物油菜Brassica campestris的抑制率分别达78.6%和89.0%。
- 4-正庚/正辛氧基苯甲脒 /
- 合成 /
- 酮醇酸还原异构酶(KARI) /
- 除草活性
Abstract: In search of herbicidal compounds,based on the structure of 4-heptyloxy(octyloxy)benzamidine and its binding pattern with ketol-acid reductoisome-rase (KARI),a series of heterocyclic compounds containing heptyloxyl or octyloxyl group on 4-position of benzene ring were designed and synthesized.The 26 synthesized compounds(22 of which are novel ) were confirmed by elemental analysis,1H NMR,IR and MS.The preliminary biological assay indicated that most of the compounds showed rice KARI inhibitory activity and herbicidal activity.Among 26 compounds, 9a and 9b showed 65.7% and 71.1% inhibitory activity on rice KARI at the concentration of 200 μg/mL; 78.6% and 89.0% on rape root (Brassica campestris) at 100 μg/mL concentration,repectively.
- 4-heptyloxy(octyloxy)benzamidine /
- synthesis /
- ketol-acid reductoisome-rase (KARI) /
- herbicidal activity

HTML全文

参考文献(10)

WANG Bao-lei(王宝雷),LI Zheng-ming(李正名).除草剂靶标酮醇酸还原异构酶(KARI)研究进展 [J].Chin J Pestic Sci (农药学学报),2004,6(1): 11-16.

WANG Bao-lei(王宝雷),WANG Jian-guo(王建国),MA Yi(马翼),et al.脒类KARI酶抑制剂的分子对接和3D-QSAR研究 [J].Acta Chimica Sinica (化学学报),2006,64(13): 1373-1378.

WANG B L,LI Y H,WANG J G,et al.Molecular Design,Synthesis and Biological Activities of Amidines as New Ketol-acid Reductoisomerase Inhibitors [J].Chin Chem Letts,2008,19: 651-654.

BIOU V,DUMAS R,COHEN-ADDAD C,et al.The Crystal Structure of Plant Acetohydroxy Acid Isomeroreductase Complexed with NADPH,Two Magnesium Ions and a Herbicidal Transition State Analog Determined at 1.65  Resolution [J].EMBO J,1997,16: 3405-3415.

LIU Fang-ming(刘方明),LU Wen-jie(鲁文杰),ZHANG Zheng-fang(张正方),et al.含2-三氟甲基苯并咪唑杂环化合物的合成 [J].Chem J Chinese Univ (高等学校化学学报),1999,20(8):1242-1247.

NAKAMURA T,SATO M,KAKINUMA H,et al.Pyrazole and Isoxazole Derivatives as New,Potent,and Selective 20-Hydroxy-5,8,11,14-eicosatetraenoic Acid Synthase Inhibitors [J].J Med Chem,2003,46(25): 5416-5427.

BROUWER W G,MACPHERSON E J,AMES R B,et al.Oxadiazole Benzoic Acid Derivatives as Herbicides:US 3964896 .1976-06-22.

LEE Y T,TA H T,DUGGLEBY R G.Cyclopropane-1,1-dicarboxylate is a Slow-,Tight-binding Inhibitor of Rice Ketol-acid Reductoisomerase [J].Plant Sci,2005,168(4): 1035-1040.

HILL C M,DUGGLEBY R G.Purified Recombinant Escherichia Coli Ketol-acid Reductoisomerase is Unsuitable for Use in a Coupled Assay of Acetohydroxyacid Synthase Activity Due to an Unexpected Side Reaction [J].Protein Expression and Purification,1999,15(1): 57-61.

WANG B L,DUGGLEBY R G,LI Z M,et al.Synthesis,Crystal Structure and Herbicidal Activity of Mimics of Intermediates of the KARI Reaction [J].Pest Manag Sci,2005,61: 407-412. (Ed.JIN S H)

施引文献

资源附件(0)

访问统计