Inter-and intramolecular photochemical reactions of fleroxacin

Organic Letters

Volumn 11, Issue 9, 2009, Pages 1875-1878

  Fasani, Elisa ^a   Monti, Sandra ^b   Manet, Ilse ^b   Tilocca, Fedele ^a   Pretali, Luca ^a   Mella, Mariella ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b Istituto per la Sintesi Organica e la Fotoreattività   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FLEROXACIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY;

FLEROXACIN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOTOCHEMISTRY;

EID: 65549167419     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900189v     Document Type: Article

References (20)

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12. Notice, however, that photoinactivation of topoisomerase IIα has been supported for related FQs, not for 1, see: Perrone, C. E.; Takahashi, K. C.; Williams, G. M. Toxicol. Sci. 2002, 69,16.
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14. For the conditions of the flash photolysis experiments, see ref 2.
15. -4 M aqueous solutions of 3 by using a 125 high-pressure mercury arc through quartz. The solutions were evaporated, the residue taken up by benzene- methanol 8:2 and treated by (trimethylsilyl)diazomethane (2.0 M solution in hexanes). The products were separated by chromatography (eluent: chloroform/methanol) as the methyl esters and characterized. Key analytic and spectroscopic data are listed in the Supporting Information.
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20. An alternative mechanism that can be considered is intramolecular electron transfer from the piperazine moiety to the heterocyclic ring. We thank a Referee for pointing to this possibility, and indeed, we think that this may have a role with other FQs, where oxidation of the amine side- chain results. This seem difficult to apply to the present case both because of the difficult C-F bond cleavage from a radical anion and because it would not lead to the observed products, compare ref 2.