Synthesis and Biological Evaluation of Pyrano[2,3-f]chromene-4,8-dione Derivatives as Potential Anticancer Agents

doi:10.1007/s40242-017-6472-8

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (2): 187-193.doi: 10.1007/s40242-017-6472-8

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Synthesis and Biological Evaluation of Pyrano[2,3-f]chromene-4,8-dione Derivatives as Potential Anticancer Agents

LI Hongshuang¹, WU Xiaming², ZHANG Ruize¹, HAO Liqiang¹, DUAN Guiyun¹, XIAO Yuliang¹, XIA Chengcai¹, LI Furong¹, YOU Guirong¹, HAN Junfen¹

1. Institute of Pharmacology, Taishan Medical University, Taian 271016, P. R. China;
2. Affiliated Hospital of Taishan Medical University, Taian 271000, P. R. China

Received:2016-11-25 Revised:2017-02-16 Online:2017-04-01 Published:2017-01-09
Contact: WU Xiaming,E-mail:wuxiaming65@163.com;DUAN Guiyun,E-mail:duanguiyun@126.com E-mail:wuxiaming65@163.com;duanguiyun@126.com
Supported by:
Supported by the National Natural Science Foundation of China(No.81671395), the Natural Science Foundation of Shandong Province, China(Nos.ZR2015BL006, ZR2013HM036), the National Innovation and Entrepreneurship Training Program for Undergraduates, China(No.201610439123) and the Science and Technology Development Project of Taian City, China(No.2015GX2049).

Abstract

Abstract:

Based on the hit 5-hydroxy-2-methyl-10-propyl-2,3-dihydro-4H,8H-pyrano[2,3-f]chromene-4,8-dione(1), a series of pyrano[2,3-f]chromene-4,8-dione derivatives was designed and synthesized using phloroglucinol as starting material. Meanwhile, a regioselective synthetic route was developed for 5-methoxy-2,3-dihydro-4H,8H-pyrano-[2,3-f]chromene-4,8-dione products(11a-11f), and their structures were further confirmed by nuclear Overhauser effect(NOE). The evaluation of anticancer activities of these compounds against four human cancer cell lines, including human glioma cell line (SHG-44), human lung cancer cell line(H1299), breast cancer cell line(MCF7) and human colon carcinoma cell line(HCT-116) in vitro shows that 5-methoxy-2,2-dimethyl-9-chloro-10-trifluormethyl-2,3-dihydro-4H,8H-pyrano[2,3-f]chromene-4,8-dione(11e) possesses the best anticancer activities with IC₅₀ values of 6.68, 7.90, 5.16 and 4.82 μmol/L, respectively. Finally, the preliminary structure-activity relationships(SARs) were summarized, which could pave the way for generating more potent anticancer agents with drug-like properties.

Key words: Anticancer activity, Phloroglucinol, Pyrano[2,3-f]chromene-4,8-dione

LI Hongshuang, WU Xiaming, ZHANG Ruize, HAO Liqiang, DUAN Guiyun, XIAO Yuliang, XIA Chengcai, LI Furong, YOU Guirong, HAN Junfen. Synthesis and Biological Evaluation of Pyrano[2,3-f]chromene-4,8-dione Derivatives as Potential Anticancer Agents[J]. Chemical Research in Chinese Universities, 2017, 33(2): 187-193.

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Synthesis and Biological Evaluation of Pyrano[2,3-f]chromene-4,8-dione Derivatives as Potential Anticancer Agents

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