- Dual functional small molecule fluorescent probes for image-guided estrogen receptor-specific targeting coupled potent antiproliferative potency for breast cancer therapy
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A strategy by integrating biological imaging into early stages of the drug discovery process can improve our understanding of drug activity during preclinical and clinical study. In this article, we designed and synthesized coumarin-based nonsteroidal type fluorescence ligands for drug-target binding imaging. Among these synthesized compounds, 3e, 3f and 3h showed potent ER binding affinity and 3e (IC50?=?0.012?μM) exhibited excellent ERα antagonistic activity, its antiproliferative potency in breast cancer MCF-7 cells is equipotent to the approved drug tamoxifen. The fluorescence of compounds 3e and 3f depended on the solvent properties and showed significant changes when mixed with ERα or ERβ in vitro. Furthermore, target molecule 3e could cross the cell membrane, localize and image drug-target interaction in real time without cell washing. Thus, the coumarin-based platform represents a promising new ER-targeted delivery vehicle with potential imaging and therapeutic properties.
- Yang, Lu,Hu, Zhiye,Luo, Junjie,Tang, Chu,Zhang, Silong,Ning, Wentao,Dong, Chune,Huang, Jian,Liu, Xianjun,Zhou, Hai-Bing
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supporting information
p. 3531 - 3539
(2017/05/29)
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- Novel coumarin compound and application thereof
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The invention relates to the technical field of novel materials and organic chemicals, in particular to a novel compound, a process technology for chemically preparing the novel compound, application of the novel compound and a radiation curing formula pr
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Paragraph 0045; 0046; 0048
(2017/08/29)
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- Metal-free C(3)-H arylation of coumarins promoted by catalytic amounts of 5,10,15,20-tetrakis(4-diethylaminophenyl)porphyrin
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The metal-free C-H arylation of coumarins was achieved in the presence of catalytic amounts of 5,10,15,20-tetrakis(4-diethylaminophenyl)porphyrin. This mild and environmentally friendly Meerwein arylation provided facile access to a broad variety of 3-arylcoumarins in synthetically useful yields.
- Kojima, Masahiro,Oisaki, Kounosuke,Kanai, Motomu
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supporting information
p. 9718 - 9721
(2016/01/09)
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- A complete switch of the directional selectivity in the annulation of 2-hydroxybenzaldehydes with alkynes
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Controlling reaction selectivity is an eternal pursuit for chemists working in chemical synthesis. As part of this endeavor, our group has been exploring the possibility of constructing different natural product skeletons from the same simple starting mat
- Zeng, Huiying,Li, Chao-Jun
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supporting information
p. 13862 - 13865
(2015/01/09)
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- Palladium catalyzed dehydrogenative arylation of coumarins: An unexpected switch in regioselectivity
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A new regioselective α-arylation of coumarins with unactivated simple arenes via a palladium-catalyzed twofold C-H functionalization is devised. This method offers an attractive new approach to synthesis of a wide variety of 3-arylcoumarins from readily accessible starting materials. This journal is The Royal Society of Chemistry 2013.
- Jafarpour, Farnaz,Hazrati, Hamideh,Mohasselyazdi, Nazanin,Khoobi, Mehdi,Shafiee, Abbas
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supporting information
p. 10935 - 10937
(2013/11/19)
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- Deracemization of α-aryl hydrocoumarins via catalytic asymmetric protonation of ketene dithioacetals
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An unprecedented catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic α-aryl hydrocoumarin derivatives are transformed into enantioenriched dithioacetal-protected hydrocoumarins in the presence of a chiral Br?nsted acid catalyst. A newly developed phosphoric acid, featuring the 3,5-bis(pentafluorothio)phenyl (3,5-(SF5) 2C6H3) substituent, is introduced. The obtained products can be easily converted into either hydrocoumarins or the corresponding chromans via simple hydrolysis or hydrogenation, respectively.
- Lee, Ji-Woong,List, Benjamin
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supporting information
p. 18245 - 18248
(2013/01/15)
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- Synthesis of 2-phenylbenzofuran derivatives and selective binding activities on estrogen receptor
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An improved chemical reaction protocol with short time and easy work-up was described here for 2-phenylbenzofuran derivatives. The final purified products, 2-phenylbenzofuran derivatives 5a-g and the intermediate diols 4a-g, were evaluated for their estrogen receptor (ER) binding affinity and selective activity in vitro. Among these fourteen tested compounds, 4g and 5g showed higher binding affinity on ER subtypes, ERα and ERβ. Compound 4g exhibited preferable ERα binding, while 5g was more estrogen selective for ERβ. The molecular docking was also performed to explore the detailed interactive interface between ER and the compounds.
- Zhang, Ping,Yang, Yewei,Zheng, Xiaoliang,Huang, Wenhai,Ma, Zhen,Shen, Zhengrong
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scheme or table
p. 270 - 274
(2012/03/11)
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- 3-ethyl-, 3-propyl- or 3-butyl-chroman and thiochroman derivatives
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A compound having the following general formula (1): in whichR1 represents an ethyl group, etc.;R2 represents a hydrogen atom, etc.;R3 represents a C1-C5 perhalogenoalkyl group, etc.;each of R4 and R5 independently represents a hydrogen atom, etc.;X represents an oxygen atom or a sulfur atom;m represents an integer of 2 to 14; andn represents an integer of 2 to 7;or an enantiomer of the compound, or a hydrate or a pharmaceutically acceptable salt of the compound or its enantiomer is advantageous in pharmaceutical use because of its anti-estrogenic activity.
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- A novel one-step synthesis of 3-phenyl-, 4-methyl-3-phenyl- And3-phenyl-4-styrylcoumarins using DCC-DMSO
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2-Hydroxybenzaldehydes 1 react with phenylacetic acid and its methoxy derivatives 2 in the presence of DCC in DMSO to afford 3-phenylcoumarins 3. Under identical conditions, 2-hydroxy-acetophenones 4 and 2'-hydroxychalcones 7 give rise to the corresponding 4-methyl-3-phenyl- and 3-phenyl-4-styrylcoumarins 6 and 8, respectively.
- Hans, Naresh,Singhi, Manasi,Sharma, Vibha,Grover
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p. 1159 - 1162
(2007/10/03)
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