CAJ | 학술논문

以取代苯甲酸为原料,经酯化、肼解、成盐和环化反应得到关键中间体4-氨基-3-芳基-1,2,4-三唑-5-硫酮,再分别与芳醛和邻苯二甲酸酐缩合得到亚胺及酰亚胺,最后经硫醚化反应合成了24个新型的含有1,2,4-三唑结构单元的亚胺及酰亚胺类化合物,其结构经质谱、红外光谱、核磁共振及元素分析确认。初步生物活性测试结果表明,在实验浓度下大部分化合物表现出一定的杀菌活性,尤其是化合物9a,9d和9e对水稻纹枯病菌的抑制活性与对照杀菌剂氟硅唑相当。初步的细胞毒性实验结果表明,化合物7c,7f和9k对人肺癌细胞(A549)的抑制活性与对照药品5-氟尿嘧啶基本处于同一水平。
이취대분갑산위원료,경지화、정해、성염화배화반응득도관건중간체4-안기-3-방기-1,2,4-삼서-5-류동,재분별여방철화린분이갑산항축합득도아알급선아알,최후경류미화반응합성료24개신형적함유1,2,4-삼서결구단원적아알급선아알류화합물,기결구경질보、홍외광보、핵자공진급원소분석학인。초보생물활성측시결과표명,재실험농도하대부분화합물표현출일정적살균활성,우기시화합물9a,9d화9e대수도문고병균적억제활성여대조살균제불규서상당。초보적세포독성실험결과표명,화합물7c,7f화9k대인폐암세포(A549)적억제활성여대조약품5-불뇨밀정기본처우동일수평。
According to active groups combination principle, a series of novel imine and imide derivatives bearing 1,2,4-triazole moiety was designed and synthesized. The key intermediate 3-substituted phenyl-4-ami-no-1,2,4-triazole-5-thiones was synthesized by esterification, hydrazinolysis, salt and cyclization reactions, and then was condensed with aromatic aldehydes and isobenzofuran-1 , 3-dione to obtain imine and imide derivatives, which were subjected to the thioetherification with suitable halides ( RX ) to produce the corre-sponding 24 novel imine and imide derivatives bearing 1,2,4-triazole moiety. The structures of target com-pounds were fully characterized by 1 H NMR, IR, mass spectroscopy and elemental analysis. The preliminary bioassay results showed that most of the compounds possessed certain fungicidal activities. At the concentration of 150 mg/L, the inhibition rates of compounds 9a, 9d and 9e against Rhizoctonia solani were very similar with the commercial fungicide Flusilazole. Meanwhile, the preliminary structure-activity relationships( SAR) were discussed in order to investigate the essential structures required for their bioactivities. In addition, their in vitro antitumor activities were evaluated against three cancer cell lines [ human alveolar epithelial cells ( A549 ) , human breast cancer cells ( MD-MBA-231 ) and human prostate cancer cells ( PC-3 M ) ] by the methyl thiazolyl tetrazolium(MTT) chromatometry method with Fluorouracil as a positive contrast drug. The bioassay data indicated that compounds 7c, 7f and 9k showed similar antiproliferation with Fluorouracil against A549 cell lines with IC50 values of 38.3, 44.6 and 36.7μmol/L, respectively. Most interestingly, compound 9k also exhibited a broad spectrum of antitumor activity against MCF-7 and MKN45 with IC50 values of 147.5 and 60.7 μmol/L, respectively.