Abstract
In this study, novel aminothiazole-paeonol derivatives were synthesized and characterized using 1H-NMR, 13C-NMR, IR, mass spectroscopy, and high performance liquid chromatography. All the new synthesized compounds were evaluated according to their anticancer effect on seven cancer cell lines. The experimental results indicated that these compounds possess high anticancer potential regarding human gastric adenocarcinoma (AGS cells) and human colorectal adenocarcinoma (HT-29 cells). Among these compounds, N-[4-(2-hydroxy-4-methoxyphenyl)thiazol-2-yl]-4-methoxybenzenesulfonamide (13c) had the most potent inhibitory activity, with IC50 values of 4.0 µM to AGS, 4.4 µM to HT-29 cells and 5.8 µM to HeLa cells. The 4-fluoro-N-[4-(2-hydroxy-4-methoxyphenyl)thiazol-2-yl]benzenesulfonamide (13d) was the second potent compound, showing IC50 values of 7.2, 11.2 and 13.8 µM to AGS , HT-29 and HeLa cells, respectively. These compounds are superior to 5-fluorouracil (5-FU) for relatively higher potency against AGS and HT-29 human cancer cell lines along with lower cytotoxicity to fibroblasts. Novel aminothiazole-paeonol derivatives in this work might be a series of promising lead compounds to develop anticancer agents for treating gastrointestinal adenocarcinoma.
Highlights
Introduction2-hydroxy-4-methoxy acetophenone (1, Figure 1), is a major component of traditionalChinese medicine
Paeonol, 2-hydroxy-4-methoxy acetophenone (1, Figure 1), is a major component of traditionalChinese medicine
2-aminothiazole scaffold was obtained by treating paeonol with thiourea iodine; the condensation-cyclization of thiourea initiated by iodine afforded compound 11
Summary
2-hydroxy-4-methoxy acetophenone (1, Figure 1), is a major component of traditionalChinese medicine. 2-hydroxy-4-methoxy acetophenone (1, Figure 1), is a major component of traditional. Paeonol is categorized as a flavonoid derivative and exhibits many remarkable biological effects, and it has been applied for anti-inflammatory [1,2], Molecules 2016, 21, 145; doi:10.3390/molecules21020145 www.mdpi.com/journal/molecules. Molecules 2016, 21, 145 analgesic [2], antioxidant [3], antidiabetic [4], anticancer [5], and antiatherogenic purposes [6]. Paeonol was2016, also21,found to protect against memory loss after ischemic stroke by reducing of amyloid. Molecules precursor protein (APP), beta-site APP cleaving enzyme (BACE), and apoptosis [7]. Paeonol was found to protect against memory loss after ischemic stroke by reducing amyloid precursor derivatives have been reported to show many attractive biological activities.
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