A new type of ketolides bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether synthesis and structure-activity relationships.
A new type of ketolides, bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and a cyclic carbonate at the C-11,12 position was prepared and the antibacterial activities of the compounds were evaluated. Some of the derivatives showed potent antibacterial activity against both Haemophilus influenzae and Streptococcus pneumoniae, which are clinically important respiratory tract pathogens. Among the derivatives prepared, compound 5s with a quinolin-4-yl moiety was found to have potent and well-balanced activity against S. pneumoniae and H. influenzae including erythromycin-resistant strains.
Nomura
Takashi
T
Discovery Research Laboratories, Shionogi & Co., Ltd., 12-4, Sagisu 5-chome, Osaka 553-0002, Japan. takashi.nomura@shinogi.co.jp
Iwaki
Tsutomu
T
Yasukata
Tatsuro
T
Nishi
Koichi
K
Narukawa
Yukitoshi
Y
Uotani
Koichi
K
Hori
Toshihiko
T
Miwa
Hideaki
H
D000081:Acetamides / Q000737:chemistry*; D000478:Alkylation; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004987:Ethers / Q000737:chemistry*; D048628:Ketolides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008171:Lung Diseases / Q000188:drug therapy; D051379:Mice; D051381:Rats; D013329:Structure-Activity Relationship
D000081:Acetamides; D000900:Anti-Bacterial Agents; D004987:Ethers; D048628:Ketolides