单、双羧酸功能化苯并咪唑衍生物的合成、结构表征及生物活性

Synthesis,structure and biological activity of monocarboxylic/biscarboxylic-functionalized benzimidazole derivatives

以苯酚为原料,经氯乙酸、邻苯二胺两步反应生成苯氧甲基苯并咪唑,再与丙烯酸甲酯经过N原子的Aza-Michael加成,接着与溴乙酸乙酯发生季铵化,然后在酸性条件下水解得到目标化合物N-羧甲基-N′-羧乙基-2-苯氧甲基苯并咪唑内鎓盐.另外,苯氧甲基苯并咪唑与氯乙酸钠反应生成另一目标化合物N-羧甲基-2-苯氧甲基苯并咪唑.经元素分析、IR和1 HNMR对其结构进行表征,用单晶X射线衍射测定了化合物6的晶体结构.结果表明,化合物6属正交晶系,Pbac空间群,晶胞参数a=0.973 67(9)nm,b=1.263 44(12)nm,c=2.294 26(4)nm,α=90°,β=90°,γ=90°,V=2.822 34(4)nm3,Z=8,F(000)=1 184.晶胞堆积图表明化合物6通过分子间氢键自组装成一维链,然后由氢键进一步连接成二维层状结构.生物活性表明,该类化合物具有植物生长调节活性、抑菌和抗真菌作用.

Synthesis of phenoxymethyl benzimidazole by a two-step reaction of phenol with chloroacetic acid and o-phenylenediamine has been studied.The latter suffers three reaction processes containing the Aza-Michael addition reacted with methyl acrylate,quaternarization and hydrolysis to give the title compound(N-carboxymethyl-N′-carboxyethyl-2-phenoxymethyl benzimidazole).Furthermore,2-phenoxymethyl benzimidazole reacts with sodium chloroacetate to give the other title compound(N-carboxymethyl-2-phenoxymethyl benzimidazole).The compounds have been characterized via elemental analysis,FTIR and 1HNMR.The molecular structure of the compound 6 is determined by single crystal X-ray diffraction.The results show that the compound crystallizes in the orthorhombic system with space group Pbac,a=0.973 67(9)nm,b=1.263 44(12)nm,c=2.294 26(4)nm,α=90°,β=90°,γ=90°,V=2.822 34(4)nm3,Z=8,F(000)=1 184.The cell packing diagram shows that the compound self-assembled with 1-dimensional chains supported by intermolecular hydrogen bonding and further formed the 2-dimensional layered molecular structure by H-bonds.The results of the bioactivity properties show that the compounds have plant growth regulating activity,antibacterial and antifungal activity.