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Journal of the Mexican Chemical Society

versión impresa ISSN 1870-249X


RAMIREZ-MARROQUIN, Oscar Abelardo et al. Anti-inflammatory Activity of Piperlotines. J. Mex. Chem. Soc [online]. 2020, vol.64, n.3, pp.181-190.  Epub 04-Jun-2021. ISSN 1870-249X.

In the present study we evaluated six α,β-unsaturated amides named piperlotines (for being isolated originally from Piper species) as new in vivo anti-inflammatory agents. In addition, we report the mechanosynthesis of two of them by mechanochemical activation of a Horner-Wadsworth-Emmons reaction. The reaction of β-amidophosphonate 4, an aromatic aldehyde and K2CO3 under grinding in a mortar and pestle afforded piperlotines 5-6 in good yields (70-88%) in short reaction times, obtaining only (E)-diastereomer. Piperlotines previously prepared were tested as anti-inflammatory and antibacterial agents. In this respect, derivatives 2 and 6 exhibited excellent in vivo anti-inflammatory activity on mice, especially trough topical administration (TPA acute inflammation model). Furthermore, piperlotine A, and compounds 2 and 6 had slight antimycobacterial activity against Mycobacterium tuberculosis (MIC = 50 µg/mL). In conclusion, the solvent-free mechanosynthesis of piperlotines produced valuable compounds that could serve as templates for further investigation in the search of better drug-like compounds for the treatment of inflammatory diseases.

Palabras llave : Mechanochemistry; piper amides; inflammation; tuberculosis.

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