Document Detail


Amikacin analogs with a fluorinated amino acid side chain.
MedLine Citation:
PMID:  2387779     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
H Hoshi; S Aburaki; S Iimura; T Yamasaki; T Naito; H Kawaguchi
Related Documents :
9516419 - Cloning, expression in yeast, and functional characterization of cyp81b1, a plant cytoc...
6402269 - Effect of increasing carbon chain length on organic acid transport by the choroid plexu...
7920739 - Expression of an ovine growth hormone transgene in mice increases arachidonic acid in c...
10331079 - Cytotoxicity of short-chain alcohols.
7159409 - Studies in vitro on shuttle systems of mouse spermatozoa.
4086479 - High performance liquid chromatographic analysis of long chain bases in intestinal glyc...
10432709 - Antiviral nucleoside drug delivery via amino acid phosphoramidates.
21298479 - Intragastrically administered lysophosphatidic acids protect against gastric ulcer in r...
6358219 - Glucosamine-derived phospholipids in escherichia coli. structure and chemical modificat...
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    
Affiliation:
Bristol-Myers Research Institute, Ltd., Tokyo Research Center, Japan.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Amikacin / analogs & derivatives*,  pharmacology,  toxicity
Animals
Bacteria / drug effects*
Chemical Phenomena
Chemistry
Diethylamines
Fluorine
Indicators and Reagents
Mice
Molecular Conformation
Molecular Structure
Chemical
Reg. No./Substance:
0/Diethylamines; 0/Indicators and Reagents; 37517-28-5/Amikacin; 38078-09-0/diethylaminosulfur trifluoride; 7782-41-4/Fluorine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


Previous Document:  3'-Hydroxyesorubicin. Synthesis and antitumor activity.
Next Document:  Early childhood bereavement.