Abstract
To discover novel potent cytotoxic diterpenoids, a series of hybrids of dehydroabietic acid containing 1,2,3-triazole moiety were designed and synthesized. The target compounds were characterized by means of FT-IR, 1H NMR, 13C NMR, ESI-MS and elemental analysis techniques. The in vitro cytotoxicity of these compounds was evaluated by standard MTT (methyl thiazolytetrazolium) assay against CNE-2 (nasopharynx), HepG2 (liver), HeLa (epithelial cervical), BEL-7402 (liver) human carcinoma cell lines and human normal liver cell (HL-7702). The screening results revealed that most of the hybrids showed significantly improved cytotoxicity over parent compound DHAA. Among them, [1-(3-fluorobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3c), and [1-(2-nitrobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3k) displayed better antiproliferative activity with IC50 (50% inhibitory concentration) values of 5.90 ± 0.41 and 6.25 ± 0.37 µM toward HepG2 cells compared to cisplatin, while they exhibited lower cytotoxicity against HL-7702. Therefore, the 1,2,3-triazole-hybrids could be a promising strategy for the synthesis of antitumor diterpenoids and it also proved the essential role of 1,2,3-triazole moiety of DHAA in the biological activity.
Highlights
IntroductionCancer has a serious impact on human health with a high mortality rate [1]
Nowadays, cancer has a serious impact on human health with a high mortality rate [1]
dehydroabietic acid (DHAA) derivatives containing 1,2,3-triazole moiety were synthesized as presented in Scheme 1
Summary
Cancer has a serious impact on human health with a high mortality rate [1]. DHAA derivatives have diverted the structural modification of dehydroabietic acid toofdevelop new anticancer been reported in recent years which showed significant antitumor property through DNA binding, agents. Has been agents, plays key role in enhancing the cytotoxicity towards theanticancer cancer cells because of its improved reported thatahybridization of 1,2,3-triazole framework other pharmacophores has the solubility,tocell permeability and pharmacokinetic parameters at thesome binding site [23,24]. It has been potential provide novel anticancer candidates [25,26,27,28]. BEL-7402 (liver) human cancer cell lines and HL-7702 normal human liver cell line
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