[1]李永双,李德江.双-三唑并[3,4-b]-[1,3,4]噻二唑类化合物的合成及抗癌活性研究[J].江西师范大学学报(自然科学版),2012,(03):297-300.
 LI Yong-shuang,LI De-jiang.The Synthesis and Anticancer Activities for Bis-Triazolo [3,4-b]-[1,3,4] Thiadiazole Derivatives[J].,2012,(03):297-300.
点击复制

双-三唑并
[3,4-b]-
[1,3,4]噻二唑类化合物的合成及抗癌活性研究
()
分享到:

《江西师范大学学报》(自然科学版)[ISSN:1006-6977/CN:61-1281/TN]

卷:
期数:
2012年03期
页码:
297-300
栏目:
出版日期:
2012-05-01

文章信息/Info

Title:
The Synthesis and Anticancer Activities for Bis-Triazolo
[3,4-b]-
[1,3,4] Thiadiazole Derivatives
作者:
李永双;李德江
三峡大学化学与生命科学学院,湖北宜昌443002
Author(s):
LI Yong-shuang LI De-jiang
关键词:
双-124-三唑并
[3
4-b]-
[1
34]噻二唑合成抗癌活性
Keywords:
bis(4-amino-5-mercapto-124-triazol-3-yl)benzene synthesis anticancer activity
分类号:
O626.24
文献标志码:
A
摘要:
间苯二甲羧酸酯化、肼解、成盐、环化成双-(4-氨基-5-巯基-1,2,4-三唑-3-基)苯(1),再与芳香酸(2a~2m)在相转移催化剂四丁基碘化铵和 POCl3作用下,高产率地制得13种1,3-双[(6-芳基)-1,2,4-三唑并
[3,4-b]-
[1,3,4]噻二唑-3-基]苯类衍生物(3a~3m),并利用 IR、1H NMR、MS 和元素分析对目标化合物的结构进行了表征.用MTT 方法评价了它们在体外对 HepG-2、 A549-1和231-2癌细胞株的体外生长抑制活性.结果表明:所合成的13个新化合物(3a~3m)均具有潜在的体外抑制癌细胞生长活性,其中3d、3h 与3i 对 HepG2和231-2的体外抑制活性最强
Abstract:
The m-phthaloylhydrazide was prepared by hydrazinolysis of the dimethyl terephthalate. The reaction of terephthaloyl with CS2/KOH in absolute ethanol gave potassium terephthaloyldithiocarbazate and then the reaction of potassium terephthaloyldithiocarbazate with hydrazine hydrate afforded 3-benzyloxyphenyl-4-amino-5-mercapto- 1,2,4-triazole(1). 1,4-Bis[(6-aryl)-1,2,4-triazolo
[3,4-b]-
[1,3,4]thiadiazole-3-yl]benzene derivatives 3a~3m were accomplished with good yields by condensing bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl) benzene (1) with dicarboxylic (2a~2m) acids in the presence of POCl3 and tetrabutylammonium iodide as catalyst. The structures of 3a~3m were confirmed by elementary analyses, IR, 1H NMR, and MS spectra, and their in vitro anticancer activity against the three cancer celllines of HepG-2, A549-1 and 231-2 was evaluated. Compounds 3d, 3h and 3i are highly active against HepG2 and 231-2.

参考文献/References:

[1] Holla B S, Gonsalves R, Shenoy S. Studies on some N-bridged heterocycles derived from bis-
[4-amino-5-mercapto-1,2,4-triazol- 3yl]alkenes [J]. Il Farmco, 1998, 53: 574-578.
[2] Holla B S, Poojary K N, Rao B S, et al. New bis-amino?mercaptotrizoles and bis-triazolothiadiazoles as possible anticancer agents [J]. J Med Chem, 2002, 37: 511-517.
[3] Li Dejiang, Fu Heqing. The synthesis and antibacterial activities of 2, 5-bis[(3-aryl) -1, 2, 4-triazolo
[3, 4-b]-
[1, 3, 4]thiadiazole-6- yl]thiophenes [J]. Phosphorus, Sulfur and Silicon, 2008, 183(9): 22229-22236.
[4] Li Dejiang, Fu Heqing. Synthesis and antibacterial activities of 1, 7-bis[(3-aryl)- 1, 2, 4-triazolo
[3, 4-b]-
[1, 3, 4]thiadiazole-6- yl]hep?tanes [J]. Heterocyclic Commmunications, 2007, 13(6): 407-412.
[5] Li Dejiang, Fu Heqing. Synthesis and antibacterial activities of 1, 5-bis[(3-aryl)-1, 2, 4-triazolo
[3, 4-b]-
[1, 3, 4]thiadiazole-6-yl]pen?tanes [J]. Heterocyclic Commmunications, 2007(6): 347- 352.
[6] Li Dejiang, Bi Xiucheng, FU He-qing. Synthesis and fungicidal activities of the synthesis and antibacterial activities of 1, 4-bis[(3-aryl)-1, 2, 4-triazolo
[3, 4-b]-
[1, 3, 4]thiadiazole-6- yl]bu?tanes [J]. Phosphorus, Sulfur and Silicon, 2007, 182(6): 1307-1314.
[7] Hu Langxi, Li Dejiang. Synthesis and antibacterial activities of bis[(3-benzyloxypheynyl)-1, 2, 4-triazolo
[3, 4-b]-
[1, 3, 4]thiadiazole derivatives [J]. Heterocyclic Commmunications, 2010, 16(3): 73-77.
[8] 王兴国, 张争光, 李德江. 2, 5-双-1, 2, 4-三唑并
[3, 4-b]-
[1,3,4]噻二唑噻吩类衍生物的合成及抗菌活性 [J]. 江西师范大学学报: 自然科学版, 2010, 34(6): 560-563.
[9] 丁浩宇, 李德江, 代中旭. 1, 4-双[(6-芳基)-1, 2, 4-三唑并
[3, 4-b]-
[1, 3, 4]噻二唑-3-基]苯类衍生物的合成及抗癌活性研究 [J]. 江西师范大学学报: 自然科学版, 2011, 35(5): 526-528.

相似文献/References:

[1]许招会,严楠,廖维林.六甲基二硅胺烷催化芳香醛与2,2-二甲基-1,3-二噁烷-4,6-二酮的缩合反应[J].江西师范大学学报(自然科学版),2012,(05):524.
 XU Zhao-hui,YAN Nan,LIAO Wei-lin.Knoevenagel Condensation Reaction of 2,2-Dimethyl-1,3-Dioxane-4,6- Dione and Aromatic Aldehydes by Hexamethyldisilazane[J].,2012,(03):524.
[2]许招会,熊斌,雷志伟.无溶剂下磷钨酸镧催化合成5-亚烃基-2,2-亚丁基-1,3-二噁烷-4,6-二酮[J].江西师范大学学报(自然科学版),2013,(04):337.
 XU Zhao-hui,XIONG Bin,LEI Zhi-wei.Solvent-Free Synthesis of 5-Alkenyl-2,2-Butylidene-1,3-Dioxane-4,6-Diones with LaPW12O40 as Catalyst[J].,2013,(03):337.

更新日期/Last Update: 1900-01-01