含苯并噻唑基乳糖基胍的合成

Synthesis of Lactosylguanidines Linked with Benzothiazolyls

2,3,6,2',3',4'.6'-七-O-乙酰基-β-乳糖基异硫氰酸酯(1)分别与2-氨基-4/6-取代苯并噻唑2a～2e反应,制得糖基硫脲3a～3e,将其在HgCl2作用下与伯胺反应,制得一系列新化合物N-烷基/芳基-N'-(4/6-取代-苯并噻唑-2-基)-N''-(2,3,6,2',3',4',6'-七-O-乙酰基-β-乳糖基)胍4～6.然后,在CH3ONa/CH3OH作用下,脱乙酰基得含苯并噻唑基的乳糖基胍类化合物7～9.所有新化合物的结构均经IR,1H NMR,MS谱和元素分析证实,所得产物均为β-构型.对代表性化合物的生物活性测试结果表明,乳糖基胍类化合物对HIV-1蛋白酶、血管紧张素转化酶(ACE)的抑制活性较差.

The reaction of 2,3,6,2′,3′,4′,6′-hepta-O-acetyl-fl-lactosyl isothiocyanate （1） with 2-amino-4/6- substituted benzothiazoles 2a-2e gave lactosylthioureas 3a-3e, which were treated with amines in the presence of HgC12 to afford a series of novel N-alkyl/aryl-N＇-（4/6-substituted benzothiazol-2-yl）-N″-peracetylated lactosylguanidines 4-6. Compounds 4-6 then reacted with the solution of CH3ONa/CH3OH, resuiting in the formation of the deacetylated lactosylguanidines 7-9. The structures of the new compounds were established on the basis of IR, ^1H NMR, mass spectral data and elemental analyses and all compounds were found to take the fl-configuration. Bioassay indicates that these lactosylguanidines show little anti-HIV-1 PR activity and little anti-angiotensin converting enzyme activity.