Next Article in Journal
Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems
Previous Article in Journal
Eco-Friendly Chitosan Production by Syncephalastrum racemosum and Application to the Removal of Acid Orange 7 (AO7) from Wastewaters
Molecules 2013, 18(7), 7661-7674; doi:10.3390/molecules18077661
Article

1,2,3-Triazole-Substituted Oleanolic Acid Derivatives: Synthesis and Antiproliferative Activity

1,* , 1, 2 and 1
Received: 30 May 2013; in revised form: 26 June 2013 / Accepted: 27 June 2013 / Published: 1 July 2013
(This article belongs to the Section Metabolites)
Download PDF [251 KB, uploaded 18 June 2014]
Abstract: Hybrid compounds are relevant products when searching for structure-activity relationships of natural products. Starting from the naturally occurring triterpene oleanolic acid, alkyl esters were prepared and treated with different aromatic azides using click chemistry to produce hybrid compounds. Some 18 new oleanolic acid derivatives were synthesized and the structures were confirmed by spectroscopic and spectrometric means. The antiproliferative activity of the new derivatives was evaluated towards normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), promyelocytic leukemia (HL-60), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells. The alkyne esters 1 and 3 showed activity on all cell lines but without selectivity (19.6–23.1 μM and 14.1–56.2 μM, respectively), their respective methyl esters were inactive. Compounds with a benzene and p-anisole attached to the triazole ring, showed no antiproliferative effect. Introduction of a chlorine atom into the benzene ring (compound 9) elicited a selective effect against AGS cells (IC50 value: 8.9 μM). The activity was lost when the COOH function at C-28 was methylated. Better antiproliferative effect was found for compounds 11 and 15 bearing a p-toluenesulphonyl group, with values in the range of 10.8–47.1 μM and 11.5–22.2 μM, respectively. The effect, however, was not associated with selectivity.
Keywords: oleanolic acid; click chemistry; antiproliferative activity oleanolic acid; click chemistry; antiproliferative activity
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.

Export to BibTeX |
EndNote


MDPI and ACS Style

Pertino, M.W.; Lopez, C.; Theoduloz, C.; Schmeda-Hirschmann, G. 1,2,3-Triazole-Substituted Oleanolic Acid Derivatives: Synthesis and Antiproliferative Activity. Molecules 2013, 18, 7661-7674.

AMA Style

Pertino MW, Lopez C, Theoduloz C, Schmeda-Hirschmann G. 1,2,3-Triazole-Substituted Oleanolic Acid Derivatives: Synthesis and Antiproliferative Activity. Molecules. 2013; 18(7):7661-7674.

Chicago/Turabian Style

Pertino, Mariano W.; Lopez, Cecilia; Theoduloz, Cristina; Schmeda-Hirschmann, Guillermo. 2013. "1,2,3-Triazole-Substituted Oleanolic Acid Derivatives: Synthesis and Antiproliferative Activity." Molecules 18, no. 7: 7661-7674.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert