5-(4-羟基苄基)-2,4-咪唑啉二酮酯类化合物的合成及生物活性

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

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,~1HNMR和元素分析进行了确证.化合物6m经X射线衍射测定:C_(18)H_(16)N_2O_5,M_r=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)nm^3,D_c=1.384 g/cm^3,Z=2,F(000)=356,μ(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200μg/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.

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 studied as CIsHI6N205, Mr=340.33, monoclinic, space group P2（1）/c,a=0.86071（17）nm,6=1.1167（2）nm,c=0.93826（2）nm,β=115.10（3）°,V=0.8166（3）nm3,Dc=1.384g/cm3,Z=2,F（000）=356,,μ（MoKα）=0.103mm^-1,finalR=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.