- Synthetic studies on the key component of the new generation of quinolonecarboxylic acid, DU-6859. 1. Synthesis of (1R,2S)-2-fluorocyclopropylamine by the use of optical resolution
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The title synthesis was achieved by employing highly cis-selective cyclopropanation of N-benzyl-N-vinylcarbamates with zinc-monofluorocarbenoid, deprotection of the formed N-benzyl-N-(cis-2-fluorocyclopropyl)carbamates, and optical resolution of the resul
- Tamura, Osamu,Hashimoto, Masaru,Kobayashi, Yuko,Katoh, Tadashi,Nakatani, Kazuhiko,Kamada, Masahiro,Hayakawa, Isao,Akiba, Toshifumi,Terashima, Shiro
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p. 3889 - 3904
(2007/10/02)
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- Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents
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A series of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acids has been prepared. These derivatives are characterized by having a fluorine atom at the 2-position on the cyclopropane ring as the N1 substituent and consist of both cis and trans stereoisomers. Structure-activity relationship studies indicate that the cis derivatives are more potent against Gram-positive bacteria than the corresponding trans counterparts, but the difference in potency against most Gram-negative bacteria is much smaller. The inhibitory effect of compounds 4, 5, 26, 27, 38, and 39 on supercoiling activity of DNA gyrase obtained from E. coli KL-16 correlated with their MICs against the same strain and also depend on their (26, 27, 38, 39) stereochemistry. Introduction of a fluorine atom on the cyclopropyl group resulted in the reduction of lipophilicity compared with the corresponding nonfluorinated quinolones.
- Atarashi,Imamura,Kimura,Yoshida,Hayakawa
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p. 3444 - 3448
(2007/10/02)
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- Synthesis and optical resolution of dl-cis-2-fluorocyclopropylamine, the key component of the new generation of quinolonecarboxylic acid, DU-6859
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The title synthesis was accomplished by featuring highly cis-selective cyclopropanation of an N-vinylcarbamate with zinc-monofluorocarbenoid followed by deprotection of the formed N-(cis-2-fluorocyclopropyl)carbamate. Optical resolution of dl-cis-2-fluoro
- Tamura,Hashimoto,Kobayashi,Katoh,Nakatani,Kamada,Hayakawa,Akiba,Terashima
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p. 3483 - 3486
(2007/10/02)
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