2. Academic Validation
  3. Derivatives of grindelic acid: from a non-active natural diterpene to synthetic antitumor derivatives

Derivatives of grindelic acid: from a non-active natural diterpene to synthetic antitumor derivatives

  • Eur J Med Chem. 2013 Sep:67:28-38. doi: 10.1016/j.ejmech.2013.06.013.
Guillermo F Reta 1,  Alejandra I Chiaramello,  Celina García,  Leticia G León,  Víctor S Martín,  José M Padrón,  Carlos E Tonn,  Osvaldo J Donadel
Affiliations

Affiliation

  • 1 INTEQUI-CONICET, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Chacabuco y Pedernera, 5700 San Luis, Argentina.
PMID: 23831507 DOI: 10.1016/j.ejmech.2013.06.013
Abstract

Using several reactions that include homologations and asymmetric epoxidations as well as Ugi and Huisgen couplings, we generated a small focused library of new derivatives from the labdane-type diterpene grindelic acid. These compounds were evaluated as cytotoxic agents against a panel of five human solid tumor cell lines (HBL-100, HeLa, SW1573, T-47D, and WiDr). The presence of the diamide functionalizations enhanced the cytotoxic effect. N-Benzyl-N-(1-(benzylamino)-2-methyl-1-oxopropan-2-yl)grindelicamide, proved to be the most active product in all cell lines tested, with values of 0.95 (±0.38) μM against HBL-100 cells.

Keywords

1,2,3-Triazole; Antitumor activity; Diamide derivatives; Labdane-type diterpenes; Multicomponent reactions.

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