Abstract
Condensation of 7-ethyl-8-hydrazinotheophylline 1 with aldohexoses 2-4 and aldopentoses 5,6 by heating in an aqueous ethanolic solution and in the presence of a catalytic amount of acetic acid gives the corresponding hitherto unknown aldehydo-sugar (7-ethyl-8-theophyllinyl)hydrazones 7-11. The structures of the sugar hydrazones 7-11 were confirmed by their elemental analyses and spectral (IR, H-1 NMR and FAB-MS) data. Acetylation of the sugar hydrazones 7-11 with acetic anhydride in pyridine at room temperature gave the corresponding poly-O-acetyl derivatives 12-16. Attempted dehydrogenative cyclization of the products 7-11 and 12-16 using various conditions did not afford the corresponding acyclo C-nucleosides (R=sugar or R'=acetylated sugar) 18. On the other hand, the reaction of 7-11 or 12-16 with bromine in acetic acid and sodium acetate afforded 8-bromo-7-ethyltheophylline 17. The structural elucidation of products is reported and also some of the products were screened for their antimicrobial activity.