Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells.
2,2-Dihydroxyarylethanones, readily prepared from the commercially available aromatic ethyl ketones, were reacted with resorcinol, 3-methoxyphenol or 2-methoxyphenol in multi steps one-pot manner promoted by trifluoroacetic acid to furnish the 2,3-diarylbenzofuran derivatives in 22-95% yield. Sixteen targeted compounds were synthesized and characterized by1H NMR,13C NMR and HRMS. MTT assay indicated that most compounds possessed effectively inhibitory activities against the proliferation of HeLa cell. Among them, 4f had the highest inhibitory activities, with the IC50being 13.40±2.04µmol/L. Cell cycle analysis, Annexin V-FITC/propidium iodide dual staining assay and western blotting analysis revealed that 4f inhibited the proliferation of Hela cell through apoptosis induction in a dose-dependent manner via obviously up-regulated the levels of Bak and Bim, while striking down-regulated the level of Bcl-2 and Bcl-xL protein.
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China.
Guo-Xue
GX
He
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China.
Jing-Mei
JM
Yuan
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China.
Hai-Miao
HM
Zhu
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China.
Kai
K
Wei
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China.
Ling-Yun
LY
Wang
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China.
Shi-Lin
SL
Kong
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China.
Dong-Liang
DL
Mo
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China. Electronic address: chengxuepan@163.com.
Cheng-Xue
CX
Pan
Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University, 15 Yu Cai Road, Guilin 541004, PR China. Electronic address: gfysglgx@163.com.
Gui-Fa
GF
Su
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002453:Cell Cycle / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D006367:HeLa Cells; D006801:Humans; D008958:Models, Molecular; D009369:Neoplasms / Q000188:drug therapy
D000970:Antineoplastic Agents; D001572:Benzofurans
2,3-Diarylbenzofuran; Antitumor activity against HeLa cells; Multistep one-pot reaction