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

Synthesis and Biological Activity of N-Alkyl/aryl-N′-(4-arylthiazol-2-yl)-N"-glycosyl Guanidines

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.

The reaction of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate （1） and 2-amino-4- arylthiazoles （2a-2b） gave glucosylthioureas 3a-3b, which then reacted with alkyl/aryl amine in the presence of HgCl2 to afford a series of new N-alkyl/aryl-N′（4-arylthiazol-2-yl）-N＂glucosyl guanidines （4a-4e and 5a-5e）. The structures of the new compounds were established on the basis of IR, ^1H NMR and MS spectra and all compounds took β-configuration. The anti-HIV and antibacterial activities of these compounds have been evaluated. Compounds 4b and 5d showed anti-HIV activity.