目的合成异穿心莲内酯糖苷及酯类衍生物。方法以DCC为缩合剂,DMAP为催化剂,异穿心莲内酯与芳香酸合成异穿心莲内酯衍生物;苄基保护的酚酸与异穿心莲内酯以DCC为缩合剂,DMAP为催化剂成酯,再经氢化合成异穿心莲内酯酚酸衍生物;异穿心莲内酯与溴代乙酰氧糖在碳酸银催化下经K-K反应后在碱性条件下脱去乙酰基形成糖苷。结果合成了4个异穿心莲内酯糖苷类衍生物及16个酯类衍生物。糖苷类衍生物与单酯类衍生物均与19-OH反应,双酯类衍生物与3-OH、19-OH成酯。所有化合物为粉末状固体。结论合成的化合物结构经1H-NMR和MS表征,其中17个为新化合物。
Objective To synthesize isoandrographolide glycoside and ester derivatives.Methods Isoandrographolide aromatic acid ester derivatives were synthesized from isoandrographolide and aromatic acids through esterification using N,N'-dicyclohexylcarbodiimide(DCC) as condensing agent and 4-dimethylaminopyridine(DMAP) as catalyst.Isoandrographolide phenolic acid ester derivatives were synthesized from isoandrographolide and benzyl-protected phenolic acids through esterification and hydrogenation in sequence using DCC as condensing agent and DMAP as catalyst.Isoandrographolide glycoside derivatives were synthesized from isoandrographolide and tetra-O-acetyl-β-D-glucopyranosyl bromide through Koenigs-Knorr reaction and then deacetylation in a basic environment using silver carbonate as a catalyst.Results Four isoandrographolide glycoside derivatives and sixteen isoandrographolide ester derivatives were synthesized.The glycoside derivatives and the monoester derivatives were obtained through esterification on the 19-OH of isoandrographolide.The diester derivatives were obtained through esterification on the 3-and 19-OH of isoandrographolide.All the derivatives were powdery solids.Conclusion All the derivatives are confirmed by 1H-NMR combined with MS,and seventeen of them are new compounds.