Abstract
New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4′ of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-β-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.
| Original language | English |
|---|---|
| Pages (from-to) | 19-39 |
| Number of pages | 21 |
| Journal | Journal of Carbohydrate Chemistry |
| Volume | 24 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2005 |
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ASJC Scopus subject areas
- Organic Chemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
Cite this
New carbohydrate derivatives of norfloxacin. / Zsoldos-Mády, Virág; Sohár, P.; Kovács, J.; Pintér, I.; Szakács, Zoltán.
In: Journal of Carbohydrate Chemistry, Vol. 24, No. 1, 2005, p. 19-39.Research output: Article
}
TY - JOUR
T1 - New carbohydrate derivatives of norfloxacin
AU - Zsoldos-Mády, Virág
AU - Sohár, P.
AU - Kovács, J.
AU - Pintér, I.
AU - Szakács, Zoltán
PY - 2005
Y1 - 2005
N2 - New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4′ of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-β-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.
AB - New classes of sugar derivatives of the antibacterial drug norfloxacin (1) were synthesized by substituting the N-4′ of the piperazinyl moiety of the molecule. Direct coupling with gluco- and galactopyranosyl units afforded glycosylamines 2-5. Introduction of urea or thiourea linkage between glycosyl and norfloxacin units was produced with the corresponding glycosyl isocyanates or isothiocyanates. For the synthesis of unprotected sugar urea compounds, a new approach was applied by using 1,2-N, O-carbonyl-β-D-glycopyranoses. Hydrazinocarbonyl-methyl- and -propyl spacers also were found appropriate for linking norfloxacin with sugar units.
KW - Glycosylamine
KW - Glycosylthiosemicarbazide
KW - Glycosylthiourea
KW - Glycosylurea
KW - Norfloxacin
UR - http://www.scopus.com/inward/record.url?scp=27844491140&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=27844491140&partnerID=8YFLogxK
U2 - 10.1081/CAR-200049410
DO - 10.1081/CAR-200049410
M3 - Article
VL - 24
SP - 19
EP - 39
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
SN - 0732-8303
IS - 1
ER -