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Synthesis and antibacterial activity of novel lincomycin derivatives. IV. Optimization of an N-6 substituent.

Authors
  • Kumura, Ko1
  • Wakiyama, Yoshinari1
  • Ueda, Kazutaka1
  • Umemura, Eijiro1
  • Hirai, Yoko1
  • Yamada, Keiko1
  • Ajito, Keiichi1
  • 1 Pharmaceutical Research Center, Meiji Seika Pharma Co., Ltd, Yokohama, Japan. , (Japan)
Type
Published Article
Journal
The Journal of antibiotics
Publication Date
Nov 08, 2017
Identifiers
DOI: 10.1038/ja.2017.143
PMID: 29115289
Source
Medline
License
Unknown

Abstract

The design and synthesis of lincomycin derivatives modified at the C-6 and C-7 positions are described. A substituent at the C-7 position is a 5-aryl-1,3,4-thiadiazol-2-yl-thio group that generates antibacterial activities against macrolide-resistant Streptococcus pneumoniae and Streptococcus pyogenes carrying an erm gene. An additional modification at the C-6 position was explored in application of information regarding pirlimycin and other related compounds. These dual modifications were accomplished by using methyl α-thiolincosaminide as a starting material. As a result of these dual modifications, the antibacterial activities were improved compared with those of compounds with a single modification at the C-7 position. The antibacterial activities of selected compounds in this report against macrolide-resistant S. pneumoniae and S. pyogenes with an erm gene were superior to those of telithromycin.The Journal of Antibiotics advance online publication, 8 November 2017; doi:10.1038/ja.2017.143.

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