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Molecules 2015, 20(5), 8666-8686; doi:10.3390/molecules20058666

Synthesis, Antiproliferative and Antifungal Activities of 1,2,3-Triazole-Substituted Carnosic Acid and Carnosol Derivatives

1
Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile
2
Facultad de Ciencias de la Salud, Universidad de Talca, Casilla 747, Talca, Chile
3
Facultad de Ciencias Bioquímicas y Farmacéuticas, Farmacognosia, Universidad Nacional de Rosario, Suipacha 531, Rosario 2000, Argentina
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 17 March 2015 / Accepted: 12 May 2015 / Published: 14 May 2015
(This article belongs to the Section Natural Products)
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Abstract

Abietane diterpenes exhibit an array of interesting biological activities, which have generated significant interest among the pharmacological community. Starting from the abietane diterpenes carnosic acid and carnosol, twenty four new triazole derivatives were synthesized using click chemistry. The compounds differ in the length of the linker and the substituent on the triazole moiety. The compounds were assessed as antiproliferative and antifungal agents. The antiproliferative activity was determined on normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells while the antifungal activity was assessed against Candida albicans ATCC 10231 and Cryptococcus neoformans ATCC 32264. The carnosic acid γ-lactone derivatives 13 were the most active antiproliferative compounds of the series, with IC50 values in the range of 43.4–46.9 μM and 39.2–48.9 μM for MRC-5 and AGS cells, respectively. Regarding antifungal activity, C. neoformans was the most sensitive fungus, with nine compounds inhibiting more than 50% of its fungal growth at concentrations ≤250 µg∙mL−1. Compound 22, possessing a p-Br-benzyl substituent on the triazole ring, showed the best activity (91% growth inhibition) at 250 µg∙mL−1 In turn, six compounds inhibited 50% C. albicans growth at concentrations lower than 250 µg∙mL−1. View Full-Text
Keywords: carnosic acid; carnosol; click chemistry; antiproliferative; antifungal carnosic acid; carnosol; click chemistry; antiproliferative; antifungal
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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. (CC BY 4.0).

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MDPI and ACS Style

Pertino, M.W.; Theoduloz, C.; Butassi, E.; Zacchino, S.; Schmeda-Hirschmann, G. Synthesis, Antiproliferative and Antifungal Activities of 1,2,3-Triazole-Substituted Carnosic Acid and Carnosol Derivatives. Molecules 2015, 20, 8666-8686.

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