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The Synthesis of 1,4‐Bis[ N ‐(4/6‐Substituted Benzothiazole‐2‐yl)‐ N ′‐Glycosylguanidino]Benzenes
Author(s) -
Tian Tian,
Cao LingHua
Publication year - 2007
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200700195
Subject(s) - chemistry , benzothiazole , isothiocyanate , glycosyl , yield (engineering) , medicinal chemistry , nitrogen , elemental analysis , stereochemistry , organic chemistry , nuclear chemistry , materials science , metallurgy
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.