引用本文:
王庆东, 薛思佳, 卞王东, 申杰峰, 蔡志娟. N-(5-邻氯苯基-2-呋喃甲酰基)甘氨酰胺及酰肼类衍生物的合成与生物活性[J]. 应用化学,
2008, 25(6): 647-650.
Citation: WANG Qing-Dong, XUE Si-Jia, BIAN Wang-Dong, SHEN Jie-Feng, CAI Zhi-Juan. Synthesis and Bioactivity of Amide and Hydrazide Derivatives of N-(5-(2-Chlorophenyl) furan-2-formyl) glycine[J]. Chinese Journal of Applied Chemistry, 2008, 25(6): 647-650.
Citation: WANG Qing-Dong, XUE Si-Jia, BIAN Wang-Dong, SHEN Jie-Feng, CAI Zhi-Juan. Synthesis and Bioactivity of Amide and Hydrazide Derivatives of N-(5-(2-Chlorophenyl) furan-2-formyl) glycine[J]. Chinese Journal of Applied Chemistry, 2008, 25(6): 647-650.
N-(5-邻氯苯基-2-呋喃甲酰基)甘氨酰胺及酰肼类衍生物的合成与生物活性
摘要:
甘氨酸、氢氧化钠及5-邻-氯苯基-2-呋喃甲酰氯以四甲基溴化铵为相转移催化剂在水-石油醚混合液中回流得N-(5-邻氯苯基-2-呋喃甲酰基)甘氨酸钠,后者经HCl酸化后分别与7种取代苯胺及5种取代苯甲酰肼在N,N'-二环己基碳二亚胺(DCC)存在下于无水DMF中反应,得到目标化合物N-(5-邻氯苯基-2-呋喃甲酰基)甘氨酰取代苯胺衍生物(4a~4g)及N-(5-邻-氯苯基-2-呋喃甲酰基)甘氨酰取代苯甲酰肼衍生物(6a~6e)的新化合物。其结构经IR、1H NMR、MS和元素分析测试确证。MTT比色法测试结果表明,部分酰胺衍生物及所有酰肼衍生物在质量浓度为1×10-5 g/mL时即可明显抑制白血病K562细胞的增殖,并且抑制作用随浓度的增加而增强,在质量浓度为1×10-4 g/mL时所有的目标化合物对白血病K562细胞的增殖均表现出较好的抑制活性。
English
Synthesis and Bioactivity of Amide and Hydrazide Derivatives of N-(5-(2-Chlorophenyl) furan-2-formyl) glycine
Abstract:
A mixture of glycine,sodium hydroxide and 5-(2-chlorophenyl) furan-2-carbonyl chloride in a water-petroleum ether solution containing phase transfer catalyst N(CH3)4 Br was refluxed,and sodium N-(5-(2-chlorophenyl) furan-2-formyl) glycine was prepared.After acidification of the sodium salt,N-(5-(2-chloro-phenyl) furan-2-formyl) glycine was obtained.With N,N'-dicyclohexylcarbodiimide (DCC) as dehydration agent,amine or hydrazide derivatives of N-(5-(2-chlorophenyl) furan-2-formyl)-glycine were prepared from the reaction of the sodium salt with substituted anilines or substituted benzohydrazides respectively in DMF.The structures of all the target compounds were confirmed by IR,1H NMR,MS,and elemental analysis.MTT assay showed that most of the target compounds possessed certain inhibition activity against K562 Cells at 1×10-4 g/mL in vitro.
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Key words:
- glycine
- / (chlorophenyl) furan-carboxylic acid
- / amide
- / hydrazide
- / derivative
- / synthesis
- / K562 cell
- / MTT assay
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