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Oxyhomologs of anandamide and related endolipids. Chemoselective synthesis and biological activity (Articolo in rivista)

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Oxyhomologs of anandamide and related endolipids. Chemoselective synthesis and biological activity (Articolo in rivista) (literal)

Anno

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Alternative label

Appendino G., Minassi A., Berton L., Schiano Moriello A., Cascio M.G., De Petrocellis L., Di Marzo V. (2006)
Oxyhomologs of anandamide and related endolipids. Chemoselective synthesis and biological activity
in Journal of medicinal chemistry; ACS, American chemical society, Washington, DC (Stati Uniti d'America)
(literal)

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Appendino G., Minassi A., Berton L., Schiano Moriello A., Cascio M.G., De Petrocellis L., Di Marzo V. (literal)

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Note

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1. Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy 2. CNR, Inst Biomol Chem, Endocannabinoid Res Grp, I-80078 Pozzuoli, NA, Italy 3. CNR, Inst Cibernet Eduardo Caianiello, Endocannabinoid Res Grp, I-80078 Pozzuoli, NA, Italy (literal)

Titolo

Oxyhomologs of anandamide and related endolipids. Chemoselective synthesis and biological activity (literal)

Abstract

The three amide oxyhomologues of the endolipids N-arachidonoylethanolamine (anandamide, AEA, 1a), N-oleoylethanolamine (OEA, 2a), and N-palmitoylethanolamine (PEA, 3a) have been prepared in a chemoselective way, capitalizing on the easy availability of O-[2-(triisopropylsilyoxy)ethyl]hydroxylamine (6) and the surprising complementary selectivity observed in the acylation of N-[2-(tert-butyldiphenylsilyloxy)ethyl]hydroxylamine (7) with the PPAA and the DCC/HOBT protocols. Reversal of the cannabinoid CB(1)/CB(2) receptor affinity ratio was observed for the first time in a derivative of anandamide (the O-alkyl-N-acyl hydroxylamine 1b), while the other oxyhomologues (1c and 1d) showed only marginal cannabimimetic activity. Compounds with unsaturated acyl chains generally retained vanilloid activity and showed an increased stability toward FAAH compared to their corresponding ethanolamides. Taken together, these observation show that oxyhomologation has a pronounced effect on both the pharmacodynamic and the pharmacokinetic properties of endogenous ethanolamides, suggesting a general relevance of this maneuver for the modification of amide pharmacophores. (literal)

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