3位苯甲酰腙和亚氨基取代硫脲取代的吲哚满二酮衍生物的合成及对AHAS的抑制活性

基于前期生物设计AHAS抑制剂的研究,设计合成了15个吲哚满二酮类衍生物,其中9个为新化合物,其结构均经过1H NMR,MS和元素分析确证,并对所有化合物进行了离体和活体活性测试.实验结果表明,这类化合物在体内和体外均具有一定的生物活性,在离体活性测试中,所有化合物在100μg/mL浓度下对拟南芥AHAS均表现出明确的抑制活性,其中化合物4d,4e,5a和5f在10μg/mL浓度下仍然对AHAS表现出45%以上的抑制率,但此类化合物除草活性普遍较差.     

Syntheses,Crystal Structures and Bioactivities of Two Isatin Derivatives

The title compounds(Z)-3-(2-(3-chloropyridin-2-yl)hydrazono)indolin-2-one(A) and 7-bromo-(Z)-3-((4-pyridinyl)carboxlichydrazono)-2-indolinone(B) have been synthesized and structurally determined by elemental analysis and single-crystal X-ray diffraction studies.Compound A(C13H8ClN4O) belongs to the orthorhombic crystal system,space group Pca21 with a = 20.799(4),b = 4.9312(10),c = 11.764(2),V = 1206.6(4)3,Mr = 271.68,Dc = 1.496 g/cm3,μ = 0.313 mm-1,F(000) = 556,Z = 4,the final R = 0.0346 and wR = 0.0831 for 2683 observed reflections with I > 2σ(I).Compound B(C14H9BrN4O2) belongs to the triclinic crystal system,space group P1 with a = 6.6834(13),b = 7.0727(14),c = 14.285(3),α = 95.56(3),β = 99.00(3),γ = 102.95(3)°,V = 643.8(2)3,Mr = 345.16,Dc = 1.780 g/cm3,μ = 3.203 mm-1,F(000) = 344,Z = 2,the final R = 0.0487 and wR = 0.1167 for 2334 observed reflections with I > 2σ(I).The preliminary herbicidal bioassay reveals that compounds A and B have some inhibition both in vivo and in vitro against AHAS.     

Synthesis and Crystal Structure of （S）-Ethyl-2-（2-methoxy-phenylsulfenamido）-3-（1H-indol-3-yl）propanoate

With an aim to discover novel AHAS inhibitors,the title compound (S)-ethyl-2(2-methoxy-phenylsulfenamido)-3-(1H-indol-3-yl)propanoate (C 21 H 22 N 2 O 4 S,M r=398.47) has been synthesized and its crystal structure was determined by single-crystal X-ray diffraction analysis.The crystal belongs to orthorhombic,space group P2 1 2 1 2 1 with a=8.078(2),b=12.824(4),c=18.788(6),V=1946.2(10) 3,Z=4,F(000)=840,D c=1.360 mg/m 3,μ=0.197 mm-1,the final R=0.0433 and wR=0.1035 for 3075 observed reflections with I > 2σ(Ⅰ).The absolute structure Flack parameter X of this compound is 0.00(8).A total of 14375 reflections were collected,of which 3431 were independent (R int=0.0437).X-ray analysis reveals that the crystal structure involves two intermolecular N-H···O and one N-H···S intermolecular hydrogen bonds with the neighboring molecules.The crystal structure was compared with our previously reported (S)-methyl 2-(4-R-phenylsulfonamido)-3-(1H-indol-3-yl)propanoate (R=H(1) and Cl(2)),which provided some useful information of these compounds.