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

Stefano D'Errico 1 , Giorgia Oliviero 1,* email, Nicola Borbone 1 , Jussara Amato 1 , Daniele D'Alonzo 2 , Vincenzo Piccialli 2 , Luciano Mayol 1  and Gennaro Piccialli 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; in revised form: 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

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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.

AMA 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(11):13036-13044.

Chicago/Turabian Style

D'Errico, Stefano; Oliviero, Giorgia; Borbone, Nicola; Amato, Jussara; D'Alonzo, Daniele; Piccialli, Vincenzo; Mayol, Luciano; Piccialli, Gennaro. 2012. "A Facile Synthesis of 5'-Fluoro-5'-deoxyacadesine (5'-F-AICAR): A Novel Non-phosphorylable AICAR Analogue." Molecules 17, no. 11: 13036-13044.

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