灯盏乙素苷元4′-L-氨基酸酯前药的合成

Synthesis of L-amino Acid Ester Prodrug of Scutellarin

目的:合成具有较强神经细胞氧化损伤保护作用及较好理化性质的灯盏乙素苷元4′-L-氨基酸酯衍生物。方法:以灯盏乙素苷元与N-Boc L-氨基酸为原料,在偶联剂DCC/DMAP的作用下缩合制备6,7-二苯缩酮保护灯盏乙素苷元4′-N-Boc L-氨基酸酯(4 a^4 c),后者经过酰氯/甲醇体系脱保护基,获得目标化合物灯盏乙素苷元4′-L-氨基酸酯(5 a^5 c)。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。结论: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′-L-氨基酸酯的制备。

Objective： To synthesize 4′-L-amino acid ester derivatives of scutellarin aglycone which would have stronger neuroprotective effect and better physiochemical properties.Methods： Scutellarin and N-Boc L-amino acid were used as starting materials to synthesize 4′-L-amino acid ester derivatives of scutellarin（4 a～4 c）protected by 6,7-diphenyl ketal in the presence of DCC/DMAP.The protective group was then removed by using acetic acid chloride / methanol system and target compounds（5 a～5 c） were obtained.Results： The structure of synthesized compounds 5 a～5 c and intermediate were confirmed by methods of 1H NMR,ESI-MS.Conclusion： This synthetic method is practical and can be used in synthesizing of scutellarin 4′ L-amino acid ester derivatives.