- Photochemistry of some non zwitterionic fluoroquinolones
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Two non zwitterionic analogues of fluoroquinolone drugs, viz. 1-ethyl-7-piperidino-8-fluoroquinol-4- one-3-carboxylic acid and 1-ethyl-7-piperidino-6,8-difluoroquinol-4-one-3-carboxylic acids have been synthesized and their photochemistry has been investigated. Both compound undergo photoheterolysis of the C8 F bond generating a triplet cation that either inserts into the 1-alkyl chain or is trapped or reduced by external nucleophiles. The reaction is analogous to that observed with the corresponding (zwitterionic) 7-piperazino derivatives, but the quantum yield is ca five times lower. This supports the rationalization that in the latter case assistance to defluorination by the N+ H bond has a determining role.
- Dichiarante, Valentina,Pretali, Luca,Fasani, Elisa,Albini, Angelo
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- An NMR study of halogenated 1,4-dihydro-1-ethyl-4-oxoquinoline-3-carboxylates
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Ethyl 1,4-dihydro-1-ethyl-4-oxoquinoline-3-carboxylate and 29 of its mono-, di-and tri-fluoro and/or -chloro derivatives were synthesized and their 1H, 13C and 19F NMR spectra were recorded. 1H, 13C and 19F chemical shifts, JHH, JFH, JCF and JFF coupling constants are reported. The 13C substituent chemical shift values of the chloro and fluoro substituents were calculated by linear multiple regression.
- Podanyi, Benjamin,Kereszturi, Geza,Vasvari-Debreczy, Lelle,Chinoin, Istvan Hermecz,Toth, Gabor
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p. 972 - 978
(2007/10/03)
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