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目的合成具有较强神经细胞氧化损伤保护作用的灯盏乙素苷元4’-N-取代氨甲基苯甲酸酯衍生物。方法灯盏乙素苷元与N-取代氨甲基苯甲酸在偶联剂N,N’-二环己基碳酰亚胺(DCC)/二甲基吡啶(DMAP)的作用下缩合后者经过酰氯/甲醇体系脱保护基,获得目标化合物(6a～6c)。并对受试化合物进行了神经细胞氧化损伤保护活性研究。结果合成的化合物及中间体均经过1H-NMR,ESI-MS进行了结构表征,确证结构与目标产物一致,受试化合物均具有较好的抗氧化活性,其中化合物6c活性明显好于维生素E、灯盏乙素。结论 4’-N-取代氨甲基苯甲酸酯前药设计方法能用于灯盏乙素苷元结构修饰,所采用的合成方法具有较好的实用性,能用于灯盏乙素苷元4’-N-取代氨甲基苯甲酸酯的制备。
OBJECTIVE: To synthesize 4’-N-substituted aminomethyl benzoate derivatives of scutellarin, which has a protective effect on oxidative damage of neurons. Methods Sizedrin aglycone and N-substituted aminomethylbenzoic acid were condensed by the coupling agent N, N’-dicyclohexylcarbodiimide (DCC) / lutidine (DMAP) / Methanol system deprotection to obtain the target compound (6a ~ 6c). The compounds were also tested for the protective activity of oxidative damage on nerve cells. Results The synthesized compounds and intermediates were characterized by 1H-NMR and ESI-MS, respectively. The structures of the compounds were confirmed to be consistent with the target compounds. The tested compounds all showed good antioxidant activity. The activity of compound 6c was significantly better than that of vitamin E, Scutellarin Conclusion 4’-N-substituted aminomethyl benzoate prodrugs can be used in the structural modification of scutellarin, the synthesis method used has good practicability and can be used for scutellarin 4 -N-substituted aminomethyl benzoate.