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2-取代硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑类化合物的合成、结构与体外抗癌活性 被引量:45

Synthesis, Structure and Antitumor Activity of 2-Alkylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole Compounds
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摘要 以天然产物没食子酸为原料经醚化、酯化、酰肼化、成盐、闭环、硫醚化六步反应合成了6个2-取代硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑类衍生物,釆用铟催化下水相合成目标化合物8,具有反应条件温和,合成收率高的特点;用IR,1HNMR,13CNMR和元素分析对各化合物进行了表征及结构确证,并用X射线单晶衍射法测定了化合物8a[2-(2-氯-5-吡啶甲基)硫醚-5-(3,4,5-三甲氧基苯基)-1,3,4-噻二唑]的晶体结构,采用MTT法进行了新化合物抑制PC3和BGC-823癌细胞体外试验,结果表明在5μmol?L-1浓度下化合物8e对PC3的抑制活性为55.71%.化合物8b对BGC-823细胞抑制活性为66.21%. Abstract Six new 2-alkylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole derivatives were synthesized from gallic acid by six steps: etherification, esterification, hydrazidation, salt formation, cyclization, and thioetherification. The synthesis of the title compounds catalyzed by indium in aqueous media was easy in process with high yield and environmental-friendliness. The products were characterized by elemental analysis, IR,^1H NMR and ^13C NMR spectra. The crystal structure of compound 8a was determined by X-ray diffraction analysis. 8a belongs to the monoclinic system with space group C2/c and cell dimensions of a= 1.5730(19) nm, b=0.5477 nm, c=4.2244 nm, β=92.015(6)°, V=3.6370(2) nm^3, Z=8, Dc= 1.497 g/cm^3,μ=0.463 mm^-1, F(000)= 1696, R1 =0.0783, wR2=0.1832. It was found that the title compounds 8 possess good antitumor activity to PC3 and BGC-823 cells in vitro by MTT method. For example, the antiproliferation activity of compound 8e to PC3 cells at the concentration of 5μmol·L^-1 at 48 h was 55.71% and the antiproliferation activity of compound 8b to BCJC-823 cells at the concentration of 5μmol·L^-1 at 48 h was 66.21%.
出处 《化学学报》 SCIE CAS CSCD 北大核心 2005年第18期1720-1726,共7页 Acta Chimica Sinica
基金 国家973计划(No.2003CB1144004) 国家自然科学基金(Nos.20442003 20362004) 高等学校博士学科点专项科研基金(No.20040657003) 教育部新世纪优秀人才计划(No.NCET04-0912)资助项目
关键词 1 3 4-噻二唑 3 4 5-三甲氧基苯基 晶体结构 抗癌活性 唑类化合物 甲氧基苯基 反应合成 体外试验 硫醚 X射线单晶衍射法 1,3,4-thiadiazole 3,4,5-trimethoxyphenyl crystal structure antitumor activity
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