马蹄金素酯类衍生物的合成及表征

Synthesis and Characterization of Matijing-Su ester derivatives

摘要:

以L-酪氨酸为起始原料，在碱性条件下与苯甲酰氯缩合得到N-苯甲酰基-O-苯甲酰基-L-酪氨酸(Ⅰ)，收率87%；然后在IBCF-NMM系统的作用下与L-苯丙氨醇缩合形成具有双酰胺结构的化合物Ⅱ，经碱水解得到化合物Ⅲ；在1,4-二氧六环和无水K2CO3的作用下与二甲氨基氯乙烷盐酸盐反应4小时后得到化合物Ⅳ，收率79%，最后用化合物Ⅳ在DMF、EDC•HCl和4-二甲氨基吡啶的条件下与有机酸反应，合成了以苯丙二肽类化合物马蹄金素[N-( N-苯甲酰基-L-苯丙氨酰基)-O-乙酰基-L-苯丙氨醇，MTS]为先导化合物的衍生物共11个，其结构经NMR、ESI-MS予以确认。

Abstract:

N-benzoyl-O-benzoyl-L-tyrosine(Ⅰ) were synthesized，in the yields of 87 %，by L-tyrosine with benzoyl chloride under the alkaline condition. Ⅱ is formed with L-Phenylglycinol condensation under the IBCF-NMM, Ⅲ was synthesized by alkaline hydrolysis of Ⅱ. 2-Dimethylaminoethyl chloride hydrochloride by n(anhydrous K2CO3)︰n(compound 3)=7︰1 gave Ⅳ with a yield of 79 % at 110 ℃ for 4 h. 11 compounds of derivatives were synthesized by compound Ⅳ in DMF, reacted with an organic acid under conditions of EDC•HCl, and 4-dimethylamino pyridine. Its structure was confirmed by NMR, ESI-MS.