Synthesis and antibacterial activities of new quinolone derivatives utilizing 1-azabicyclo[1.1.0]butane

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• 作者：Yoshifumi Ikee ; Kana Hashimoto ; Masaaki Nakashima ; Kazuhiko Hayashi ; Shigeki Sano ; Motoo Shiro ; Yoshimitsu Nagao
• 关键词：Azabicyclobutane ; Azetidine ; New quinolone ; Antibacterial agent ; MRSA
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2007
• 出版时间：15 February 2007
• 年：2007
• 卷：17
• 期：4
• 页码：942-945
• 全文大小：197 K

文摘

The ring-opening reactions of 1-azabicyclo[1.1.0]butane 3 with thiols 6a–f gave 3-sulfenylazetidine derivatives 7a–f in 50-92 % yields. Treatment of 3 with aromatic amines 11a–e and dibenzylamine 11f in the presence of Mg(ClO₄)₂ afforded the corresponding 3-aminoazetidine derivatives 12a–f in 24–53 % yields. These azetidine derivatives were introduced into the C7 position of a quinolone nucleus 8 to afford the corresponding fluoroquinolones 9a–f and 13a–f in 21–83 % yields. Some of them exhibited superior antibacterial activity against quinolone-susceptible MRSA in comparison with clinically used fluoroquinolones, such as levofloxacin, ciprofloxacin, and gatifloxacin.