Document Detail

Amikacin analogs with a fluorinated amino acid side chain.
MedLine Citation:
PMID:  2387779     Owner:  NLM     Status:  MEDLINE    
The synthesis and biological activity of kanamycin A derivatives with an omega-amino-alpha-fluoroalkanoyl side chain on the 1-amino group are described. The fluorinated amino acids (4) for the side chain were prepared by fluorination of the alpha-hydroxy esters (2) with diethylaminosulfur trifluoride (DAST) with accompanying the Walden inversion. The reaction products varied with the amino protective groups employed, chain length of the alkanoic acids and the presence or absence of base. The fluorinated side chain was introduced to 1-free-NH2 kanamycin A (12) by the conventional active ester method and subsequent deblocking reactions afforded the desired final products (13-17). Of the derivatives prepared, 1-N-[(S)-4-amino-2-fluorobutyryl]kanamycin A (2'''-deoxy-2'''-fluoroamikacin, 14) showed the best overall activity profile, nearly the same as that of amikacin. Preparation and antibacterial activity of several aminoglycoside antibiotics with the 1-N-(S)-4-amino-2-fluorobutyryl side chain are also discussed.
H Hoshi; S Aburaki; S Iimura; T Yamasaki; T Naito; H Kawaguchi
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of antibiotics     Volume:  43     ISSN:  0021-8820     ISO Abbreviation:  J. Antibiot.     Publication Date:  1990 Jul 
Date Detail:
Created Date:  1990-09-25     Completed Date:  1990-09-25     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0151115     Medline TA:  J Antibiot (Tokyo)     Country:  JAPAN    
Other Details:
Languages:  eng     Pagination:  858-72     Citation Subset:  IM    
Bristol-Myers Research Institute, Ltd., Tokyo Research Center, Japan.
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MeSH Terms
Amikacin / analogs & derivatives*,  pharmacology,  toxicity
Bacteria / drug effects*
Chemical Phenomena
Indicators and Reagents
Molecular Conformation
Molecular Structure
Reg. No./Substance:
0/Diethylamines; 0/Indicators and Reagents; 37517-28-5/Amikacin; 38078-09-0/diethylaminosulfur trifluoride; 7782-41-4/Fluorine

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