Synthesis and In Vitro Anticancer Activity of Novel Dehydroabietic Acid-Based Acylhydrazones

Abstract

In order to develop novel chemotherapeutic agents with potent anticancer activities, a series of dehydroabietic acid (DHA) derivatives bearing an acylhydrazone moiety were designed and synthesized by the condensation between dehydroabietic acylhydrazide (3) and a variety of substituted arylaldehydes. The inhibitory activities of these compounds against CNE-2 (nasopharynx), HepG2 (liver), HeLa (epithelial cervical), and BEL-7402 (liver) human carcinoma cell lines were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay in vitro. The screening results revealed that many of the compounds showed moderate to high levels of anticancer activities against the tested cancer cell lines and some displayed similar potent inhibitory activities to the commercial anticancer drug cisplatin, while they exhibited lower cytotoxicity against normal human liver cell (HL-7702). Particularly, compound 4w, N’-(3,5-difluorobenzylidene)-2-(dehydroabietyloxy)acetohydrazide, with an IC50 (50% inhibitory concentration) value of 2.21 μM against HeLa cell, was about 17-fold more active than that of the parent compound, and showed remarkable cytotoxicity with an IC50 value of 14.46 μM against BEL-7402 cell. These results provide an encouraging framework that could lead to the development of potent novel anticancer agents.

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

“…For example, a series of 3-ethoxy-4-hydroxybenzaldehyde oxime esters were synthesized and evaluated for their in vitro antifungal activity against three pathogenic fungi and antibacterial activity against three bacterial strains, and the structure-activity relationship was also preliminarily summarized [ 26 ]. In continuation of our interest in the bioactive properties of natural product-based compounds [ 27 , 28 , 29 , 30 , 31 , 32 , 33 ], a series of novel 3-caren-5-one oxime esters were designed and synthesized by integrating bioactive oxime esters into the skeleton of 3-carene. Structural characterization and antifungal evaluation of all the title compounds were carried out as well.…”

Synthesis and Cytotoxicity Evaluation of Dehydroabietic Acid Derivatives Bearing Nitrate Moiety

“…Particularly, it is reported that numerous NO-donating hybrids have the potential to provide novel anticancer candidates with low toxicity and high efficacy against drug-resistant cancers. [22][23][24][25][26][27] Enlightened by these findings, together with our previous studies on the modification of natural products, [28][29][30][31] a modification via integrating DHAA and nitrate pharmacophore into one molecule to generate a novel dehydroabietic acid NO donor hybrids was conducted. The screening of the cytotoxicity of these hybrids against four human cancer cell lines and normal human cell were carried on.…”

Synthesis of Bioactive Compounds from 3-Carene (II): Synthesis, Antifungal Activity and 3D-QSAR Study of (Z)- and (E)-3-Caren-5-One Oxime Sulfonates

“…Our research group has recently reported the synthesis of a series of structurally modified 3-carene derivatives and found that some of the title compounds exhibited excellent antifungal activity [21]. Herein, as continuation of our work on natural product-based bioactive compounds [22,23,24,25,26,27], a series of novel 3-caren-5-one oxime sulfonates were designed and synthesized by integrating bioactive oxime sulfonates into the skeleton of 3-carene. Structural characterization and antifungal evaluation of all the target compounds were carried out as well.…”