Synthesis and Antiproliferative Activity of Some Novel Triazole Derivatives from Dehydroabietic Acid

Molecules

Mariano Walter Pertino¹  Valery Verdugo¹  Cristina Theoduloz² 

[1] Instituto de Química de Recursos Naturales, Universidad de Talca, Casilla 747, Talca, Chile;Facultad de Ciencias de la Salud, Universidad de Talca, Casilla 747, Talca, Chile

关键词: dehydroabietic acid;    click chemistry;    antiproliferative activity;   

DOI  :  10.3390/molecules19022523

来源: mdpi

【 摘 要 】

Dehydroabietic acid (DHA) is a naturally occurring diterpene with different and relevant biological activities. Previous studies have shown that some DHA derivatives display antiproliferative activity. However, the reported compounds did not include triazole derivatives. Starting from DHA (8,11,13-abietatrien-18-oic acid), and its alcohol dehydroabietinol (8,11,13-abietatrien-18-ol), four alkyl esters were prepared. The alkyl terpenes were treated with different aromatic azides to synthesize hybrid compounds using click chemistry. Some 16 new DHA hybrids were thus synthesized and their structures were confirmed by spectroscopic and spectrometric means. The antiproliferative activity of the new compounds was assessed towards human cell lines, namely normal lung fibroblasts (MRC-5), gastric epithelial adenocarcinoma (AGS), lung cancer (SK-MES-1) and bladder carcinoma (J82) cells. Better antiproliferative effect was found for compound 5, with an IC₅₀ of 6.1 μM and selectivity on SK-MES-1 cells. Under the same experimental conditions, the IC₅₀ of etoposide, was 1.83 µM.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.