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Photochemistry of some non zwitterionic fluoroquinolones

Paper ID Volume ID Publish Year Pages File Format Full-Text
26967 43990 2013 8 PDF Available
Title
Photochemistry of some non zwitterionic fluoroquinolones
Abstract

•Two non zwitterionic analogues of fluoroquinolone drugs have been synthesized.•The photochemistry has been investigated.•Both compound undergo photoheterolysis of the C8F bond generating a triplet cation.•The quantum yield is low.•Assistance to defluorination by the N+H bond has a determining role.

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 C8F 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.

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Keywords
Fluoroquinolones; Photoheterolysis; Aryl cation; Zwitterion
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 265, 1 August 2013, Pages 41–48
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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Price was $35.95
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