17460-45-6Relevant articles and documents
Hydrolysis of the GlcNAc oxazoline: deamidation and acyl rearrangement
Jha, Rajesh,Davis, Jeffrey T.
, p. 125 - 134 (1995)
The specific deamidation of 2-acetamido-1,3,4,6-tetra-O-acetyl-α-D-glucopyranose is achieved by p-toluenesulfonic acid-promoted hydrolysis of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)--2-oxazoline 2 to give quantitative formation of the 1,3,4,6-tetra-O-actyl-2-amino-2-deoxy-α-D-glucopyranose p-toluenosulfonate (5d).This two-step procedure provides an amino sugar which may be readily acylated to give novel glycoconjugates.Altermatively, base-catalyzed O-1 --> N-2 acyl rearrangemet of the amino tosylate 5d gives the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose 4 as a 9:1 mixture of α and β anomers.Thus, hydrolysis of GlcNAc oxazoline 2 gives the amino-ester 5 as the kinetic product and the amido-alcohol 4 as the thermodynamic product.Keywords: GlcNAc oxazoline; Deamidation; Acyl rearrangement
Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives
Mohammed, Aya A. M.,Okechukwu, Patrick N.,Shehadeh, Mayadah B.,Suaifan, Ghadeer A. R. Y.
, (2020/07/04)
Herein we report the design, synthesis and biological evaluation of structurally modified ciprofloxacin, norfloxacin and moxifloxacin standard drugs, featuring amide functional groups at C-3 of the fluoroquinolone scaffold. In vitro antimicrobial testing against various Gram-positive bacteria, Gram-negative bacteria and fungi revealed potential antibacterial and antifungal activity. Hybrid compounds 9 (MIC 0.2668 ± 0.0001 mM), 10 (MIC 0.1358 ± 00025 mM) and 13 (MIC 0.0898 ± 0.0014 mM) had potential antimicrobial activity against a fluoroquinolone-resistant Escherichia coli clinical isolate, compared to ciprofloxacin (MIC 0.5098 ± 0.0024 mM) and norfloxacin (MIC 0.2937 ± 0.0021 mM) standard drugs. Interestingly, compound 10 also exerted potential antifungal activity against Candida albicans (MIC 0.0056 ± 0.0014 mM) and Penicillium chrysogenum (MIC 0.0453 ± 0.0156 mM). Novel derivatives and standard fluoroquinolone drugs exhibited near-identical cytotoxicity levels against L6 muscle cell-line, when measured using the MTT assay.
GLYCOSYLATED 3-SUBSTITUTED FLUOROQUINOLONE DERIVATIVES, PREPARATION METHODS THEREOF, AND THEIR USE IN THE TREATMENT OF ANTIMICROBIAL INFECTIONS
-
, (2020/10/20)
The present disclosure relates to 3-substituted fluoroquinolone derivatives, and more particularly to glycosylated 3-substitutred fluoroquinolone derivatives, methods of preparation thereof, and uses thereof for treating microbial infections.