Synthesis and evaluation of aminothiazole-paeonol derivatives as potential anticancer agents

Chia Ying Tsai, Mohit Kapoor, Ying Pei Huang, Hui Hsien Lin, Yu Chuan Liang, Yu Ling Lin, Su Chin Huang, Wei Neng Liao, Jen Kun Chen, Jer Shing Huang, Ming-Hua Hsu

Research output: Contribution to journalArticle

8 Citations (Scopus)

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.

Original languageEnglish
Article number145
JournalMolecules
Volume21
Issue number2
DOIs
Publication statusPublished - 2016 Feb 1

Fingerprint

HT29 Cells
Antineoplastic Agents
Adenocarcinoma
Cells
Nuclear magnetic resonance
Lead compounds
Derivatives
HeLa Cells
Inhibitory Concentration 50
evaluation
High performance liquid chromatography
Fibroblasts
synthesis
Cytotoxicity
cells
Fluorouracil
Cell Line
cultured cells
Spectroscopy
cancer

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Tsai, Chia Ying ; Kapoor, Mohit ; Huang, Ying Pei ; Lin, Hui Hsien ; Liang, Yu Chuan ; Lin, Yu Ling ; Huang, Su Chin ; Liao, Wei Neng ; Chen, Jen Kun ; Huang, Jer Shing ; Hsu, Ming-Hua. / Synthesis and evaluation of aminothiazole-paeonol derivatives as potential anticancer agents. In: Molecules. 2016 ; Vol. 21, No. 2.
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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.",
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Tsai, CY, Kapoor, M, Huang, YP, Lin, HH, Liang, YC, Lin, YL, Huang, SC, Liao, WN, Chen, JK, Huang, JS & Hsu, M-H 2016, 'Synthesis and evaluation of aminothiazole-paeonol derivatives as potential anticancer agents', Molecules, vol. 21, no. 2, 145. https://doi.org/10.3390/molecules21020145

Synthesis and evaluation of aminothiazole-paeonol derivatives as potential anticancer agents. / Tsai, Chia Ying; Kapoor, Mohit; Huang, Ying Pei; Lin, Hui Hsien; Liang, Yu Chuan; Lin, Yu Ling; Huang, Su Chin; Liao, Wei Neng; Chen, Jen Kun; Huang, Jer Shing; Hsu, Ming-Hua.

In: Molecules, Vol. 21, No. 2, 145, 01.02.2016.

Research output: Contribution to journalArticle

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AU - Huang, Ying Pei

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AU - Liang, Yu Chuan

AU - Lin, Yu Ling

AU - Huang, Su Chin

AU - Liao, Wei Neng

AU - Chen, Jen Kun

AU - Huang, Jer Shing

AU - Hsu, Ming-Hua

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