4'''-N-demethylspiramycin derivatives: synthesis and evaluation of effectiveness against drug-resistant bacteria

Toshiaki Sunazuka; Hiroko Shudo; Kenichiro Nagai; Kiminari Yoshida; Yukie Yamaguchi; Hideaki Hanaki; Satoshi Omura

doi:10.1038/ja.2008.127

4'''-N-demethylspiramycin derivatives: synthesis and evaluation of effectiveness against drug-resistant bacteria

J Antibiot (Tokyo). 2008 Mar;61(3):175-84. doi: 10.1038/ja.2008.127.

Authors

Toshiaki Sunazuka¹, Hiroko Shudo, Kenichiro Nagai, Kiminari Yoshida, Yukie Yamaguchi, Hideaki Hanaki, Satoshi Omura

Affiliation

¹ Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University and The Kitasato Institute, Minato-ku, Tokyo, Japan.

PMID: 18503196
DOI: 10.1038/ja.2008.127

Abstract

18-amino-4''-O-benzoyl-4'''-N-demethyl-18-deoxospiramycins were designed and synthesized. Synthetic strategy involved selective demethylation of the dimethylamino group in forosamine, benzoylation of the hydroxyl group at the C4'' position and reductive N-amination of the formyl group. Antibacterial characteristics of spiramycin derivatives were tested. The derivatives exhibited promising activity against drug-resistant bacterial strains.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / pharmacology*
Bacteria / drug effects*
Carbohydrate Sequence
Drug Resistance, Bacterial / drug effects*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mass Spectrometry
Methicillin Resistance
Microbial Sensitivity Tests
Molecular Sequence Data
Spectrophotometry, Infrared
Spiramycin / analogs & derivatives*
Spiramycin / chemical synthesis
Spiramycin / pharmacology
Staphylococcus aureus / drug effects

Substances

4'''-N-demethylspiramycin
Anti-Bacterial Agents
Indicators and Reagents
Spiramycin