4-(Arylamino)phenyl α-d-glucopyranosides as potential anti-HIV agents

✍ Scribed by Josie C. Briggs; Alan H. Haines

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 446 KB
• Volume: 282
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(95)00379-7

✦ Synopsis

Our recent interest in aryl-substituted phenyl C~-D-glucopyranosides as potential anti-HIV agents [I-3] led us to examine 4-(arylamino)phenyl a-o-glucopyranosides (1) in this context, since we regarded these glycosides as a logical modification of 4-(arylsulfonylamino)phenyl a-D-glucopyranosides (2), one of which had been shown [3] to possess weak anti-HIV activity against HIV-I ilIB in infected cell cultures. Glycosides of the type 2 were found [3] to be remarkably eflective competitive inhibitors of yeast ¢:e-t)-glucosidase, an observation of relevance in regard to .'mti-HIV activity since nojirimycin, castanosperlnine, and some of their deriwltives which show such antivirai activity also act competitively against certain glycosidases [4]. We now report the synthesis of a series of glycosides 3=6 and some representative examples of lipophilic O-acyl derivatives, compounds 711t), and results of anti.HIV tests with these compounds.