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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.
Keywords
Anticancer activity
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Phloroglucinol
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Pyrano[2,3-f]chromene-4,8-dione
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Hongshuang Li, Xiaming Wu, Ruize Zhang, Liqiang Hao, Guiyun Duan, Yuliang Xiao, Chengcai Xia, Furong Li, Guirong You, Junfen Han.
Synthesis and biological evaluation of pyrano[2,3-f]chromene-4,8-dione derivatives as potential anticancer agents.
Chemical Research in Chinese Universities, 2017, 33(2): 187-193 DOI:10.1007/s40242-017-6472-8
| [1] |
StewartB. W., WildC. P.World Cancer Report 2014, 2015
|
| [2] |
BhanotA., SharmaR., NoolviM. N.Int. J. Phytomedicine, 2011, 319
|
| [3] |
KingstonD. I.J. Nat. Prod., 2009, 723507.
|
| [4] |
CraggG. M., KingstonD. G. I., NewmanD. M.Anticancer Agents from Natural Products, 2012Boca RatonCRC Press/Taylor & Francis Group1
|
| [5] |
ZhaoH., NeamatiN., HongH., MazumderA., WangS., SunderS., MilneG. W. A., PommierY., BurkeT. R.J. Med. Chem., 1997, 402242.
|
| [6] |
KontogiorgisC. A., Hadjipavlou-LitinaD. J.J. Med. Chem., 2005, 48206400.
|
| [7] |
HwuJ. R., LinS. Y., TsayS. C., ClercqE. D., LeyssenP., NeytsJ.J. Med. Chem., 2011, 5472114.
|
| [8] |
NeytsJ., ClercqE. D., SinghaR., ChangY. H., DasA. R., ChakrabortyS. K., HongS. C., TsayS. C., HsuM. H., HwuJ. R.J. Med. Chem., 2009, 5251486.
|
| [9] |
WuY., ShangG., TangQ., ZhangB., WangE.Chem. Res. Chinese Universities, 2016, 323357.
|
| [10] |
ChenY., WangS., XuX., LiuX., YuM., ZhaoS., LiuS., QiuY., ZhangT., LiuB. F., ZhangG.J. Med. Chem., 2013, 56114671.
|
| [11] |
RomaG., BraccioM. D., GrossiG., PirasD., LeonciniG., BruzzeseD., SignorelloM. G., FossaP., MostiL.J. Med. Chem., 2007, 50122886.
|
| [12] |
PisaniL., MuncipintoG., MisciosciaT. F., NicolottiO., LeonettiF., CattoM., CacciaC., SalvatiP., Soto-OteroR., Mendez-AlvarezE., PasseleuC., CarottiA.J. Med. Chem., 2009, 52216685.
|
| [13] |
BarianaD. S.J. Med. Chem., 1970, 133544.
|
| [14] |
SashidharaK. V., KumarM., KhedgikarV., KushwahaP., ModukuriR. K., KumarA., GautamJ., SinghD., SridharB., TrivediR.J. Med. Chem., 2013, 561109.
|
| [15] |
LiuM. M., ChenX. Y., HuangY. Q., FengP., GuoY. L., YangG., ChenY.J. Med. Chem., 2014, 57229343.
|
| [16] |
LiuZ., LiD., JiangD., XiaoC., SongZ., JinY.Chem. Res. Chinese Universities, 2013, 2961125.
|
| [17] |
DandriyalJ., SinglaR., KumarM., JaitakV.Eur. J. Med. Chem., 2016, 119: 141.
|
| [18] |
MaT., LiuL., XueH., LiL., HanC., WangL., ChenZ., LiuG.J. Med. Chem., 2008, 51: 1432.
|
| [19] |
ChandlerI. M., MclntyreC. R., SimpsonT. J.J. Chem. Soc., Pekin Trans., 1992, 1: 2271.
|
| [20] |
XieL., TakeuchiY., CosentinoL. M., McPhailA. T., LeeK. H.J. Med. Chem., 2001, 44: 664.
|
| [21] |
XieX., YanY., ZhuN., LiuG.Eur. J. Med. Chem., 2014, 76: 67.
|
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Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH
