128376-64-7Relevant articles and documents
Photocatalytic C–X borylation of aryl halides by hierarchical SiC nanowire-supported Pd nanoparticles
Jiao, Zhi-Feng,Zhao, Ji-Xiao,Guo, Xiao-Ning,Guo, Xiang-Yun
, p. 357 - 363 (2020)
Hierarchical SiC nanowire-supported Pd nanoparticles showed high photocatalytic activity for the C-X (X = Br, I) borylation of aryl halides at 30 °C. The SiC/Pd Mott-Schottky contact enhances the rapid transfer of the photogenerated electrons from SiC to the Pd nanoparticles. As a result, the concentrated energetic electrons in the Pd nanoparticles can facilitate the cleavage of C-I or C-Br bonds, which normally requires high-temperature thermal processes. We show that the present Pd/SiC photocatalyst is capable of catalyzing the transformation of a large variety of aryl halides to their corresponding boronate esters under visible light irradiation, with excellent yields.
Reactive Oxygen Species (ROS)-sensitive prodrugs of the tyrosine kinase inhibitor crizotinib
Ahmed, Esra,Bielec, Bjoern,Heffeter, Petra,Keppler, Bernhard K.,Kowol, Christian R.,Poetsch, Isabella
, (2020)
Tyrosine kinase inhibitors revolutionized cancer therapy but still evoke strong adverse effects that can dramatically reduce patients' quality of life. One possibility to enhance drug safety is the exploitation of prodrug strategies to selectively activate a drug inside the tumor tissue. In this study, we designed a prodrug strategy for the approved c-MET, ALK, and ROS1 tyrosine kinase inhibitor crizotinib. Therefore, a boronic-acid trigger moiety was attached to the 2-aminopyridine group of crizotinib, which is a crucial position for target kinase binding. The influence of the modifications on the c-MET- and ALK-binding ability was investigated by docking studies, and the strongly reduced interactions could be confirmed by cell-free kinase inhibition assay. Furthermore, the newly synthesized compounds were tested for their activation behavior with H2O2 and their stability in cell culture medium and serum. Finally, the biological activity of the prodrugs was investigated in three cancer cell lines and revealed a good correlation between activity and intrinsic H2O2 levels of the cells for prodrug A. Furthermore, the activity of this prodrug was distinctly reduced in a non-malignant, c-MET expressing human lung fibroblast (HLF) cell line.
Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water
Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg
, p. 1842 - 1851 (2018)
A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
Discovery of phenyl-linked symmetric small molecules as inhibitors of the programmed cell death-1/programmed cell death-ligand 1 interaction
Wu, Yizhe,Zhang, Yu,Guo, Yu,Pan, Zhichao,Zhong, Shichun,Jin, Xinxin,Zhuang, Weihao,Chen, Sikang,Gao, Jian,Huang, Wenhai,Dong, Xiaowu,Che, Jinxin
, (2021)
Programmed cell death-1/programmed cell death ligand 1 (PD-1/PD-L1) is one of the most promising targets in the field of immune checkpoint blockade therapy. Beginning with our exploration of linkers and structure-activity relationship research, we found that the aromatic ring could replace the linker and aryl group to maintain the satisfactory activity of classic triaryl scaffold inhibitor. Based on previous studies, we designed and synthesized a series of C2-symmetric phenyl-linked compounds, and further tail optimization afforded the inhibitors, which displayed promising inhibitory activity against the PD-1/PD-L1 interaction with IC50 value at the single nanomolar range (C13–C15). Further cell-based PD-1/PD-L1 blockade bioassays indicated that these C2-symmetric molecules could significantly inhibit the PD-1/PD-L1 interaction at the cellular level and restore T cells' immune function at the safety concentrations. The discovery of these phenyl-linked symmetric small molecules showed the potential of simplified-linker and C2-symmetric strategy and provided a basis for developing symmetric small molecule inhibitors of PD-1/PD-L1 interaction. Moreover, C13 and C15 performed stable binding modes to PD-L1 dimeric after computational docking and dynamic simulation, which may serve as a good starting point for further development.
Use of in situ isopropoxide protection in the metal-halogen exchange of arylboronates
Jiang, Qin,Ryan, Meagan,Zhichkin, Paul
, p. 6618 - 6620 (2007)
(Chemical Equation Presented) Isopropoxide protection of arylboronates allowed their use in metal-halogen exchange reactions. The isopropoxide- protected borate species were obtained from a boronate or in situ from dibromoarenes. meta- and para-dibromoare
Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system
Fuerstner, Alois,Seidel, Guenter
, p. 541 - 543 (2002)
(formula presented) Aryl chlorides bearing electron-withdrawing groups react with bis(pinacol)borane 1 to give aryl boronates in good to excellent yields in the presence of a catalyst formed in situ from Pd(OAc)2 and the imidazolium chloride 2. The reaction is greatly accelerated when carried out under microwave heating.
Behavior of Supramolecular Assemblies of Radiometal-Filled and Fluorescent Carbon Nanocapsules In?Vitro and In?Vivo
Ge, Haobo,Riss, Patrick J.,Mirabello, Vincenzo,Calatayud, David G.,Flower, Stephen E.,Arrowsmith, Rory L.,Fryer, Tim D.,Hong, Young,Sawiak, Steve,Jacobs, Robert M.J.,Botchway, Stanley W.,Tyrrell, Rex M.,James, Tony D.,Fossey, John S.,Dilworth, Jonathan R.,Aigbirhio, Franklin I.,Pascu, Sofia I.
, p. 437 - 460 (2017)
Hybrid materials based on supramolecularly assembled single-walled carbon nanotubes (SWNTs) are generated for positron emission tomography (PET), magnetic resonance imaging, and fluorescence imaging. The all-in-one imaging probe allows quantitative imaging from subcellular resolution to whole tissue regions. The SWNTs can be exposed to aqueous solutions of non-radioactive and radioactive metal salts in the presence of fullerenes and β-D-glucan. Encapsulating 64Cu ions achieves a minimum of 69% incorporation of radiochemical. The results suggest that this method can be extended to other metal ions of medical relevance, such as zirconium(IV)-89 or rhenium(VII)-188, which are used for medical imaging or radiotherapy, respectively. The in vivo uptake of 64Cu(II)@SWNT@β-D-glucan in Wistar rats allows the investigation of organ biodistribution by microPET. Radioactivity rapidly accumulates predominantly in the lungs and myocardium with peak uptakes of 4.8 ± 0.9 standardized uptake value. Furthermore, such materials are fully traceable in cells by multiphoton fluorescence lifetime imaging with near-infrared excitation (910 nm).
An improved procedure for the synthesis of arylboronates by palladium-catalyzed coupling reaction of aryl halides and bis(pinacolato)diboron in polyethylene glycol
Lu, Jie,Guan, Zhong-Zhi,Gao, Jian-Wu,Zhang, Zhan-Hui
, p. 537 - 541 (2011)
A new protocol has been developed for the synthesis of arylboronates by a coupling reaction of aryl halides and bis(pinacolato)diboron using bis(triphenylphosphine)palladium dichloride/sodium acetate/polyethylene glycol 600 [Pd(PPh3)2Cl2/NaOAc/PEG 600] as an efficient catalytic system. Copyright
Nitro-substituted stilbeneboronate pinacol esters and their fluoro-adducts. Fluoride ion induced polarity enhancement of arylboronate esters
Oehlke, Alexander,Auer, Alexander A.,Jahre, Ina,Walfort, Bernhard,Rueffer, Tobias,Zoufala, Petra,Lang, Heinrich,Spange, Stefan
, p. 4328 - 4339 (2007)
(Chemical Equation Presented) A series of stilbeneboronate pinacol cyclic esters, containing none to three nitro groups, have been synthesized by various olefination reactions and characterized by X-ray single-crystal structure analysis. A stilbeneboronat
One-pot preparation of unsymmetrical biaryls via Suzuki cross-coupling reaction of aryl halide using phase-transfer catalyst in a biphasic solvent system
Miura, Masanori,Koike, Takanori,Ishihara, Tsukasa,Sakamoto, Shuichi,Okada, Minoru,Ohta, Mitsuaki,Tsukamoto, Shin-Ichi
, p. 667 - 674 (2007)
A one-pot synthetic method of unsymmetrical biaryls was developed via the Suzuki cross-coupling reaction of aryl halide using a phase-transfer catalyst in a biphasic solvent system. Copyright Taylor & Francis Group, LLC.
