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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (01): 72-78. 上一篇    下一篇

研究论文

5-(4-羟基苄基)-2,4-咪唑啉二酮酯类化合物合成及生物活性

王进敏，韩金涛，张春艳，邱立红，王明安*   

  1. (中国农业大学应用化学系 北京 100193)
  • 收稿日期:2009-04-19 修回日期:2009-06-29 发布日期:2010-01-20
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn, wangmingan2003@yahoo.com
  • 基金资助:

    国家自然科学基金和十一五科技支撑计划

Synthesis and Biological Activities of 5-(4-Hydroxybenzyl)hydantoin Esters

Wang,Jinmin，Han,Jintao，Zhang,Chunyan，Qiu,Lihong，Wang,Mingan*   

  1. (Department of Applied Chemistry，China Agricultural University，Beijing 100193)
  • Received:2009-04-19 Revised:2009-06-29 Published:2010-01-20

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为了发现高效、低毒、低残留的农药先导化合物，模拟AdSS酶天然抑制剂的活性结构，以L-酪氨酸为起始原料，经过关环和酯化等反应合成了24个新的5-(4-羟基苄基)-2,4-咪唑啉二酮酯系列化合物6a～6x，它们的结构通过IR，1H NMR和元素分析进行了确证。化合物6m经X射线衍射测定: C18H16N2O5，Mr＝340.33，单斜晶系，空间群 P2(1)/c，a＝0.86071(17) nm，b＝1.1167(2) nm，c＝0.93826(2) nm，β＝115.10(3)°，V＝0.8166(3) nm3，Dc＝1.384 g/cm3，Z＝2，F(000)＝356，m(Mo Kα)＝0.103 mm－1，final R＝0.0359，wR＝0.0998。初步生物活性实验结果表明，在200 mg/mL浓度下，部分化合物对小麦和拟南芥的生长有一定的抑制作用，而部分化合物对玉米的生长有促进作用。

关键词: AdSS酶抑制剂, 5-(4-羟基苄基)-2,4-咪唑啉二酮羧酸酯, 生物活性

To develop novel pesticide lead compounds with high activity，low toxicity and low residue，24 novel 5-(4-hydroxybenzyl)-2,4-imidazolidinedione (hydantoin) esters were synthesized with cyclization and esterification using L-tyrosine as raw material by simulating the structure of natural inhibitor against AdSS synthetase，and structurally confirmed by m.p.，IR，1H NMR and elemental analysis。X-ray diffraction analysis of 6m was studies as C18H16N2O5，Mr＝340.33，monoclinic，space group P2(1)/c，a＝0.86071(17) nm， b＝1.1167(2) nm，c＝0.93826(2) nm，β＝115.10(3)°，V＝0.8166(3) nm3，Dc＝1.384 g/cm3，Z＝2，F(000)＝356，m(Mo Kα)＝0.103 mm－1，final R＝0.0359，wR＝0.0998。The preliminary bioassay results indicated that some of these compounds had certain inhibition activities against Triticum aestivum and Arabidopsis thaliana，while some of them could promote the growth of Zea mays at the concentration of 200 μg/mL.

Key words: AdSS inhibitor, 5-(4-hydroxybenzyl)-2,4-imidazolidinedione ester, biological activity