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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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