Details

Autor(en) / Beteiligte

• Furuuchi, Takeshi
• Miura, Tomoaki
• Kurihara, Ken-ichi
• Yoshida, Takuji
• Watanabe, Takashi
• Ajito, Keiichi

Titel

Design and synthesis of novel leucomycin analogues modified at the C-3 position. Part II: 3- O-(3-Aryl-2-propenyl)leucomycin analogues

Ist Teil von

• Bioorganic & medicinal chemistry, 2008-04, Vol.16 (8), p.4401-4418

Ort / Verlag

England: Elsevier Ltd

Erscheinungsjahr

2008

Quelle

MEDLINE

Beschreibungen/Notizen

• The design and synthesis of 16-membered macrolides modified at the C-3 position are described. 3- O-(3-Aryl-2-propenyl)leucomycin A 7 analogues showed improved in vitro antibacterial activities against clinically important pathogens. The design and synthesis of 16-membered macrolides modified at the C-3 position are described. Starting from fully protected intermediate ( 5), appropriate modifications including Heck reaction were performed to furnish 3- O-(3-aryl-2-propenyl)leucomycin A 7 analogues ( 9a– 9m). These leucomycin A 7 derivatives showed improved in vitro antibacterial activities against clinically important pathogens including erythromycin-resistant Streptococcus pneumoniae (ERSP). SAR analysis of derivatives modified at the C-3 and C-3″ positions suggested that single modification at C-3 or C-3″ was effective for in vitro antibacterial activity.