N-烷基/芳基-N′-(4-芳基噻唑-2-基)-N"-糖基胍的合成及生物活性研究

2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基异硫氰酸酯(1)与2-氨基-4-取代苯基噻唑(2a～2b)反应,生成糖基硫脲衍生物3a～3b,再在伯胺存在下经氯化汞脱硫,得到一系列新的N-烷基/芳基-N'-(4-芳基噻唑-2-基)-N"-糖基胍类化合物(4a～4e,5a～5e).所有新化合物的结构均经IR,1HNMR,MS谱和元素分析证实,所得产物均为β-构型.生物活性测试结果表明,化合物4b和5d对HIV-1PR表现出了较高的抑制活性.

糖基胍的研究进展

许多含有糖基和胍基官能团的天然的及合成的化合物,都具有很强的生物活性,近年来引起研究者的极大兴趣。随着具有高活性的含有糖基和胍基天然产物不断被发现,糖基胍类化合物的合成方法也在不断地改进,包括嗜硫剂以及新型胍基化试剂的使用,使糖基胍类化合物的合成变得更加高效。本文对天然的及合成的糖基胍基化合物的结构及合成方法及其应用进行了较全面的阐述,并对该领域的发展方向提出了我们的看法。

Synthesis of a series of guanidine substituted derivatives of aminoglycosides

A novel method to prepare guanidine substituted aminoglycoside derivatives was developed.Free guanidine reacted with Cbz-protected aminoglycosides to produce guanidinylcarbonyl substituted derivatives.A methoxycarbonyl-protected intermediate was isolated,and the mechanism of guanidinylcarbonyl modification was proposed.With this method,six per- or part-guanidylcarbonyl substituted aminoglycosides were successfully obtained in good yields.Their in vitro antibacterial activities were essayed.