Acta Chimica Sinica ›› 2005, Vol. 63 ›› Issue (18): 1720-1726. Previous Articles     Next Articles

Original Articles

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

宋宝安*,陈才俊,杨松,金林红,薛伟, 张素梅,邹志辉,胡德禹,刘刚   

  1. (贵州大学精细化工研究开发中心 教育部绿色农药和农业生物工程重点实验室 贵阳 550025)
  • 收稿日期:2005-03-02 修回日期:2005-05-16 出版日期:2005-09-28 发布日期:2010-12-10
  • 通讯作者: 宋宝安

Synthesis, Structure and Antitumor Activity of 2-Alkylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole Compounds

SONG Bao-An*, CHEN Cai-Jun, YANG Song, JIN Lin-Hong, Xue Wei, ZHANG Su-Mei, ZOU Zhi-Hui, HU De-Yu, LIU Gang   

  1. (Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education of China,
    Research and Development Center for Fine Chemicals, Guizhou Universtry, Guiyang 550025)
  • Received:2005-03-02 Revised:2005-05-16 Online:2005-09-28 Published:2010-12-10
  • Contact: SONG Bao-An

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) nm3, Z=8, Dc=1.497 g/cm3, =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 5 μmol•L-1 at 48 h was 55.71% and the antiproliferation activity of compound 8b to BGC-823 cells at the concentration of 5 μmol•L-1 at 48 h was 66.21%.

Key words: 1,3,4-thiadiazole, 3,4,5-trimethoxyphenyl, crystal structure, antitumor activity