CHEMICAL MODIFICATION OF FORTIMICINS: PREPARATION OF 4-N-SUBSTITUTED FORTIMICIN B

Among the new aminoglycoside antibiotic family of fortimicins, components A, C and D have higher activity compared to their 4-N-deacylated components B and KE. Synthesis and antibacterial activities of 4-N-acyl- and 4-N-alkyl-fortimicin B derivatives are described. 4-N-Acylfortimicin B's, which...

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Bibliographic Details
Published in:Journal of antibiotics 1979, Vol.32(4), pp.371-378
Main Authors: SATO, MORIYUKI, MORI, YASUKI
Format: Article
Language:English
Subjects:
Aminoglycosides - chemical synthesis
Aminoglycosides - pharmacology
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Bacteria - drug effects
Microbial Sensitivity Tests
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Summary:Among the new aminoglycoside antibiotic family of fortimicins, components A, C and D have higher activity compared to their 4-N-deacylated components B and KE. Synthesis and antibacterial activities of 4-N-acyl- and 4-N-alkyl-fortimicin B derivatives are described. 4-N-Acylfortimicin B's, which are relatively unstable in alkaline conditions, were converted to stable 4-N-alkyl derivatives with diborane. The activity is greatly affected by the 4-N-substituents, and the presence of hydrophilic group(s) is necessary to confer activity on the derivatives. 4-N-(2-Aminoethyl)-, 4-N-(4-amino-2-hydroxybutyl)- and 4-N-(2-hydroxy-4-methylaminobutyl)-fortimicin B are the most potent compounds among them.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.32.371