6967-88-0Relevant articles and documents
Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium
Romero, Kevin J.,Keylor, Mitchell H.,Griesser, Markus,Zhu, Xu,Strobel, Ethan J.,Pratt, Derek A.,Stephenson, Corey R.J.
, p. 6499 - 6504 (2020)
The first total synthesis of the resveratrol tetramers vitisin A and vitisin D is reported. Electrochemical generation and selective dimerization of persistent radicals is followed by thermal isomerization of the symmetric C8b-C8c dimer to the C3c-C8b isomer, providing rapid entry into the vitisin core. Computational results suggest that this synthetic approach mimics Nature's strategy for constructing these complex molecules. Sequential acid-mediated rearrangements consistent with the proposed biogenesis of these compounds afford vitisin A and vitisin D. The rapid synthesis of these complex molecules will enable further study of their pharmacological potential.
Visible light-induced mono-bromination of arenes with BrCCl3
Fan, Jiali,Wei, Qiancheng,Zhu, Ershu,Gao, Jing,Cheng, Xiamin,Lu, Yongna,Loh, Teck-Peng
supporting information, p. 5977 - 5980 (2021/06/18)
A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.
Cu-Catalyzed: O -alkylation of phenol derivatives with alkylsilyl peroxides
Sakurai, Shunya,Kano, Taichi,Maruoka, Keiji
supporting information, p. 81 - 84 (2021/01/14)
A Cu-catalyzed O-alkylation of phenol derivatives using alkylsilyl peroxides as alkyl radical precursors is described. The reaction proceeds smoothly under mild reaction conditions and the use of two different ligands with a Cu catalyst provides a wide range of products. A mechanistic study suggested that the reaction proceeds via a radical mechanism. This journal is
Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
supporting information, p. 19257 - 19262 (2019/12/02)
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics
Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung
supporting information, p. 4448 - 4452 (2018/10/17)
Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.
Zwitterionic-Salt-Catalyzed Site-Selective Monobromination of Arenes
Xiong, Xiaodong,Tan, Fei,Yeung, Ying-Yeung
supporting information, p. 4243 - 4246 (2017/08/23)
A zwitterionic-salt-catalyzed electrophilic monobromination of arenes with high regioselectivity has been developed. Under mild reaction conditions, a wide range of monobrominated aromatic compounds can be obtained in excellent yields. The reaction can be operated using an extremely low catalyst loading (0.05 mol %) with the inexpensive brominating agent N-bromosuccinimide. The versatility of this catalytic protocol has been demonstrated by the scale-up reaction with a 0.01 mol % catalyst loading to provide the selectively halogenated compound in quantitative yield.
Design, syntheses, and characterization of pharmacophore based chemokine receptor CCR5 antagonists as anti prostate cancer agents
Arnatt, Christopher K.,Zaidi, Saheem A.,Zhang, Zhu,Li, Guo,Richardson, Amanda C.,Ware, Joy L.,Zhang, Yan
, p. 647 - 658 (2013/10/22)
Accumulating evidence has shown multiple roles that chemokine receptor CCR5 may play to promote the progression of several types of cancer. The mechanism of such promotion is believed to involve chronic inflammation that creates a microenvironment which e
IMPROVED MODULATORS OF HEC1 ACTIVITY AND METHODS THEREFOR
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Paragraph 00151, (2013/06/27)
Compounds, compositions, and methods for modulation of Hec1/Nek2 interaction are provided. Such compounds disrupt Nek2/Hec1 binding and may be useful as chemotherapeutic agents for neoplastic diseases
Analogues of fenarimol are potent inhibitors of trypanosoma cruzi and are efficacious in a murine model of chagas disease
Keenan, Martine,Abbott, Michael J.,Alexander, Paul W.,Armstrong, Tanya,Best, Wayne M.,Berven, Bradley,Botero, Adriana,Chaplin, Jason H.,Charman, Susan A.,Chatelain, Eric,Von Geldern, Thomas W.,Kerfoot, Maria,Khong, Andrea,Nguyen, Tien,McManus, Joshua D.,Morizzi, Julia,Ryan, Eileen,Scandale, Ivan,Thompson, R. Andrew,Wang, Sen Z.,White, Karen L.
supporting information; experimental part, p. 4189 - 4204 (2012/07/27)
We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC50s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.
Synthesis of 1,4-bis[2,2-bis(4-alkoxyphenyl)vinyl]benzenes and side chain modulation of their solid-state emission
An, Peng,Shi, Zi-Fa,Dou, Wei,Cao, Xiao-Ping,Zhang, Hao-Li
supporting information; experimental part, p. 4364 - 4367 (2010/11/17)
Figure Presented. A series of 1,4-bis[2,2-bis(4-alkoxyphenyl)vinyl]benzene molecules with aggregation-induced emission (AIE) activity were synthesized. The conformations and packing arrangements of these molecules in the solid state can be adjusted by changing the side chains, which subsequently modulates their solid-state emission. The fluorescence quantum yield of 1e with the n-C 6H13 side chain in the solid state could reach up to 60.3% in the solid state.