3698-04-2Relevant academic research and scientific papers
Annulative synthesis of benzofurans from general alkenyl sulfoxides and phenols via pummerer/sigmatropic cascade
Hori, Mitsuki,Yanagi, Tomoyuki,Murakami, Kei,Nogi, Keisuke,Yorimitsu, Hideki
, p. 302 - 311 (2019/02/25)
In addition to ketene dithioacetal monoxides that were specially designed and have been used so far, general alkenyl sulfoxides of moderate reactivity have now become applicable as substrates in the trifluoroacetic anhydride-mediated annulation with pheno
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.
Synthesis of Polyaryl-Substituted Olefins via a Rh(III)-Catalyzed One-Pot Reaction Using N-Phenoxyacetamides, Ketones, and Hydrazines
Zhang, Yan,He, Yu,Li, Lisha,Ji, Mingming,Li, Xiao-Zong,Zhu, Gangguo
, p. 2898 - 2903 (2018/03/09)
A Rh(III)-catalyzed one-pot reaction of N-phenoxyacetamides, ketones, and hydrazines for a facile access to disubstituted and trisubstituted ethylenes is reported. In this method, various ketones are transformed into donor-donor diazo compounds, which engage in insertion with N-phenoxyacetamides, following β-H elimination under Rh(III) catalysis to generate (E)-polyaryl-substituted olefins. This chemistry features simple starting materials, mild reaction conditions, and good functional group tolerance.
A facile one-pot synthesis of 2,3-diarylated benzo[b]furans via relay NHC and palladium catalysis
Jia, Yanyan,Li, Tuanjie,Yu, Chenxia,Jiang, Bo,Yao, Changsheng
, p. 1982 - 1987 (2016/02/18)
An efficient one-pot synthesis of 2,3-diarylated benzo[b]furans was realized through the relay catalysis of N-Heterocyclic Carbene (NHC) and palladium from substituted 2′-bromodiphenylbromomethanes and aryl aldehydes. The easy availability of the starting
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.
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
, 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
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 new synthetic strategy for the synthesis of bioactive stilbene dimers. A direct synthesis of amurensin H
Kraus, George A.,Gupta, Vinayak
experimental part, p. 7180 - 7183 (2010/03/03)
2,3-Diarylbenzofurans are efficiently generated by the cyclization of ortho-benzyloxybenzophenones using the hindered phosphazene base P4-t-Bu.
