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2005
Carbohydrates
Carbohydrates
U 0500
New Carbohydrate Derivatives of Norfloxacin. — Sugar derivatives, derived from
antibacterial title drug, are synthesized by substituting the secondary amine group
28- 196 the
of the piperazinyl moiety. Direct coupling with galacto- and glucopyranosyl units provides glycosylamines like (III). Glycosyl and norfloxacin units can be connected
through an urea or thiourea linkage, cf. (V), by using the corresponding glycosyl isocyanates or isothiocyanates. A new approach to unprotected sugar urea compounds,
e.g. (IX), is achieved by the use of 1,2-N,O carbonyl-β-D-glycopyranoses, e.g. (VIII).
To link a sugar unit to the piperazinyl group, hydrazinocarbonyl-alkyl groups turn out
to be appropriate spacers. The spacer is built-up from the corresponding ethoxycarbonyl-alkyl derivatives, e.g. (XI). The antimicrobial activities of the stable acylhydrazine
(XII) and acylthiosemicarbazide (XIV) are lower than those of perfloxacin. —
(ZSOLDOS-MADY*, V.; SOHAR, P.; KOVACS, J.; PINTER, I.; SZAKACS, Z.; J.
Carbohydr. Chem. 24 (2005) 1, 19-39; Res. Group Struct. Chem. Spectrosc., Hung.
Acad. Sci., H-1518 Budapest, Hung.; Eng.) — H. Hoennerscheid
2005
Carbohydrates
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