6723-06-4Relevant academic research and scientific papers
Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis
Fan, Xin,He, Huaiyu,Li, Jiao,Luo, Guoyong,Zheng, Yuanyuan,Zhou, Jian-Kang,He, Juan,Pu, Wenchen,Zhao, Yun
, p. 2235 - 2244 (2019/04/30)
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1)participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5)and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29)as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.
Au-catalyzed synthesis of benzofurans from phenols and alkynes using molecular oxygen
Liao, Jinqiang,Guo, Pengfeng,Chen, Qinlin
, p. 22 - 25 (2016/02/19)
An efficient Au-catalyzed transformation for the synthesis of benzofurans from phenols and alkynes using molecular oxygen has been developed. The reaction proceeds smoothly with commercially available, eco-friendly oxidant and affords the products in moderate to good yields. This reaction is a facile approach for the formation of C - C and C-O bonds.
A one-pot domino C-H, C-C activation in coumarins: A fast track to 2,3-diaryl benzo[b]furans
Khoobi, Mehdi,Molaverdi, Fatemeh,Jafarpour, Farnaz,Abbasnia, Masoumeh,Kubicki, Maciej,Shafiee, Abbas
supporting information, p. 11713 - 11716 (2015/07/15)
An approach to synthesize 2,3-diaryl benzo[b]furans using coumarins and aryl bromides is developed. This state-of-the-art strategy capitalizes on a palladium-catalyzed one-pot decarbonylative diarylation of coumarins, paving the way to achieve biologicall
One-pot synthesis of 2,3-diarylbenzofurans via sequential iodocyclization and Pd-catalyzed Suzuki coupling reactions of 2-alkynylanisoles with boronic acids in water
Han, Jiang-Sheng,Chen, Su-Qin,Zhong, Ping,Zhang, Xiao-Hong
supporting information, p. 3148 - 3155 (2015/10/06)
An efficient approach for the one-pot synthesis of 2,3-diarylbenzofurans via sequential iodocyclization and Pd-catalyzed Suzuki coupling reaction of 2-alkynylanisoles with boronic acids in water is reported. The protocol utilizes water as the solvent and
Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity
Liu, Guixia,Shen, Yangyang,Zhou, Zhi,Lu, Xiyan
, p. 6033 - 6037 (2013/07/19)
Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)-catalyzed C-H functionalization of N-phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho-hydroxyphenyl-substituted enamides or cyclization to deliver benzofurans with high selectivity (see scheme; Cp=C5Me5). Copyright
Facile synthesis of benzofurans via copper-catalyzed aerobic oxidative cyclization of phenols and alkynes
Zeng, Wei,Wu, Wanqing,Jiang, Huanfeng,Huang, Liangbin,Sun, Yadong,Chen, Zhengwang,Li, Xianwei
supporting information, p. 6611 - 6613 (2013/07/26)
Regioselective synthesis of polysubstituted benzofurans using a copper catalyst and molecular oxygen from phenols and alkynes in a one-pot procedure has been reported. The transformation consists of a sequential nucleophilic addition of phenols to alkynes and oxidative cyclization. A wide variety of phenols and alkynes can be used in the same manner.
Direct access to benzo[b]furans through palladium-catalyzed oxidative annulation of phenols and unactivated internal alkynes
Kuram, Malleswara Rao,Bhanuchandra,Sahoo, Akhila K.
supporting information, p. 4607 - 4612 (2013/05/22)
2,3-Disubstituted benzo[b]furans are prepared in one step from commercially available phenols and readily accessible unactivated internal alkynes (see scheme). This Pd-catalyzed oxidative annulation has a broad substrate scope and allows access to a wide range of benzo[b]furans. Copyright
Benzofuran synthesis via copper-mediated oxidative annulation of phenols and unactivated internal alkynes
Zhu, Ruyi,Wei, Jiangbo,Shi, Zhangjie
, p. 3706 - 3711 (2013/11/19)
The first example of copper-mediated oxidative annulation of phenols and unactivated internal alkynes to afford benzofuran derivatives was reported. Various phenols and unactivated internal alkynes were successfully employed. Mechanistic studies disclosed a new strategy on annulations of alkynes with phenols through reversible electrophilic carbocupration of phenol followed by alkyne insertion and cyclization.
A convenient one-pot synthesis of 4-methyl-3-phenyl-, 3-aryl- and 3-aryl-4-phenylcoumarins
Kamat, Shrivallabh P.,D'Souza, Asha M.,Paknikar, Shashikumar K.,Beauchamp, Philip S.
, p. 242 - 246 (2007/10/03)
Thermal condensation of 2′-hydroxyacetophenones 1a-e with phenylacetic acid 2a in refluxing diphenyl ether gives 4-methyl-3-phenylcoumarins 3a-e. Similarly, reaction of 2-hydroxybenzaldehydes 1f-m and 2-hydroxybenzo-phenones 1n-p with phenylacetic acids 2a-d gives the corresponding 3-arylcoumarins 3f-m and 3-aryl-4-phenylcoumarins 3n-p respectively. Formation of esters 4 and 5 and benzofuran 6 is also observed.
