The Synthesis of 1,4‐Bis[ N ‐(4/6‐Substituted Benzothiazole‐2‐yl)‐ N ′‐Glycosylguanidino]Benzenes

The starting material O ‐protected glycosyl isothiocyanate ( 1˜3 ) was refluxed with 1,4‐diaminobenzene in CHCl 3 under nitrogen atmosphere to give 1,4‐bis( N ‐glycosyl)thioureidobenzene ( 4˜6 ). Then 1,4‐bis[ N ‐(4/6‐substituted benzothiazole‐2‐yl)‐ N ′‐glycosylguanidino]benzenes ( 8a˜8e , 9a˜9e , 10a˜10e ) were obtained in good yield by reaction of compounds ( 4˜6 ) with 2‐amino‐4/6‐benzothizoles ( 7a˜7e ) and HgCl 2 in the presence of TEA in DMF. The structures of all 18 new compounds were confirmed by IR, 1 H NMR, LC‐MS and elemental analysis. The bioactivity of anti‐HIV‐1 protease (HIV‐1 PR) and against angiotensin converting enzyme (ACE) have been evaluated.