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Molecules 2012, 17(11), 13036-13044; doi:10.3390/molecules171113036
Article

A Facile Synthesis of 5'-Fluoro-5'-deoxyacadesine (5'-F-AICAR): A Novel Non-phosphorylable AICAR Analogue

1, 1,* , 1, 1, 2, 2, 1 and 1
1 Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131, Napoli, Italy 2 Dipartimento di Scienze Chimiche, Università degli Studi di Napoli Federico II, Via Cintia 21, 80126, Napoli, Italy
* Author to whom correspondence should be addressed.
Received: 29 September 2012 / Revised: 31 October 2012 / Accepted: 31 October 2012 / Published: 2 November 2012
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Abstract

The substitution of a hydroxyl group by a fluorine atom in a potential drug is an efficient reaction that can, in principle, improve its pharmacological properties. Herein, the synthesis of the novel compound 5′-fluoro-5′-deoxyacadesine (5′-F-AICAR), a strict analogue of AICAR that cannot be 5′-phosphorylated to ZMP by cellular kinases, is reported.
Keywords: AICAR; ZMP; AMPK; AMPK activation; fluorinated nucleosides; fluorination; imidazole nucleosides; nucleoside analogues; modified nucleosides AICAR; ZMP; AMPK; AMPK activation; fluorinated nucleosides; fluorination; imidazole nucleosides; nucleoside analogues; modified nucleosides
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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D'Errico, S.; Oliviero, G.; Borbone, N.; Amato, J.; D'Alonzo, D.; Piccialli, V.; Mayol, L.; Piccialli, G. A Facile Synthesis of 5'-Fluoro-5'-deoxyacadesine (5'-F-AICAR): A Novel Non-phosphorylable AICAR Analogue. Molecules 2012, 17, 13036-13044.

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