787-69-9Relevant articles and documents
Effects of P-glycoprotein on the transport of DL0410, a potential multifunctional anti-Alzheimer agent
Pang, Xiaocong,Wang, Lin,Kang, De,Zhao, Ying,Wu, Song,Liu, Ai-Lin,Du, Guan-Hua
, (2017)
In our study, we attempted to investigate the influences of P-glycoprotein (P-gp) on DL0410, a novel synthetic molecule for Alzheimer’s disease (AD) treatment, for intestinal absorption and blood-brain barrier permeability in vitro and related binding mechanisms in silico. Caco-2, MDCK, and MDCK-MDR1 cells were utilized for transport studies, and homology modelling of human P-gp was built for further docking study to uncover the binding mode of DL0410. The results showed that the apparent permeability (Papp) value of DL0410 was approximately 1 × 10?6 cm/s, indicating the low permeability of DL0410. With the presence of verapamil, the directional transport of DL0410 disappeared in Caco-2 and MDCK-MDR1 cells, suggesting that DL0410 should be a substrate of P-gp, which was also confirmed by P-gp ATPase assay. In addition, DL0410 could competitively inhibit the transport of Rho123, a P-gp known substrate. According to molecular docking, we also found that DL0410 could bind to the drug binding pocket (DBP), but not the nucleotide binding domain (NBD). In conclusion, DL0410 was a substrate as well as a competitive inhibitor of P-gp, and P-gp had a remarkable impact on the intestine and brain permeability of DL0410, which is of significance for drug research and development.
Effects of length and number of aromatic rings in carboxylic acid ligands on structure and optical properties of lead(II) coordination polymers
Hashemzadeh, Alireza,Amini, Mostafa M.,Najafi, Ezzatollah,Khavasi, Hamid Reza
, p. 5741 - 5753 (2017)
To systematically examine the effects of the length and number of aromatic rings in carboxylic acid ligands on the structure and properties of lead(II) coordination polymers, terephthalic acid (L1) and 4,4-biphenyl dicarboxylic acid (L2) as primary ligands and 1-(dimethylamino)propan-2-ol (L3) as ancillary ligand were used for preparation of two new lead(II) coordination polymers: [Pb2L2 1L3(DMF)]n (1) and [PbL2L3]n (2). Single-crystal X-ray diffraction analysis was used to determine the crystal structure of the prepared compounds. The results showed that the length of the π-conjugation system of the aromatic carboxylic acid ligands was a primary factor controlling the structure of the coordination compounds. Connecting Pb(II) atoms using ligands L1 and L3 led to formation of compound 1 with two-dimensional network structure, while use of ligands L3 and L2 resulted in formation of compound 2 with zigzag one-dimensional (1D) polymeric network structure. Study of the thermal behavior of the prepared compounds revealed that the structure and type of the ligands in the coordination compounds affected their thermal stability. Investigation of the optical properties of the compounds demonstrated that changing the length of the π-conjugation system of the aromatic carboxylic acid ligands in the structure of the coordination compounds can be used to tune their photophysical properties.
A series of triple-stranded lanthanide(III) helicates: Syntheses, structures and single molecular magnets
Gao, Xingrui,Li, Hongfeng,Chen, Peng,Sun, Wenbin,Yan, Pengfei
, p. 1 - 7 (2017)
Bis-β-diketones have been proven to be effective for the construction of multiple-stranded helicates, where there commonly are two distinct Ln3+centers with subtle geometric difference. In this study, a series of triple-stranded helicates [Ln2(BTB)3(DME)2]·C6H14have been prepared with the ligand H2BTB and trivalent metallic ions, respectively [Ln?=?La (1), Ce (2), Pr (3), Eu (4), Dy (5), Ho (6) and Yb (7), H2BTB?=?4,4′-bis(4,4,4-trifluoro-1,3-dioxobutyl)biphenyl and DME?=?dimethoxyethane]. All products have been fully characterized by IR spectroscopy, elemental analysis, thermogravimetric analysis, and single-crystal X-ray diffraction analyses. Structural analysis reveals that 1–7 are isostructurally crystallized in the orthorhombic space group of Pna21and each Ln3+ion is ligated to six O atoms of three BTB ligands and two O atoms of one DME molecule. Interestingly, DME molecule as a chelator to the Ln3+centers has played a unique role in the crystallization of the triple-stranded helicate 1–7. Magnetic measurement shows that 5 displays significant single-molecule magnetic property, exhibiting magnetic slow relaxation. And the large separation between Dy3+ions in the same helicates leads to two distinct magnetic relaxation processes.
An imidazolium ionic liquid having covalently attached an oxime carbapalladacycle complex as ionophilic heterogeneous catalysts for the Heck and Suzuki-Miyaura cross-coupling
Corma, Avelino,García, Hermenegildo,Leyva, Antonio
, p. 8553 - 8560 (2004)
An oxime carbapalladacycle, analogous to that used as catalyst in homogeneous phase, has been derivatized to increase its ionophilicity by introducing an imidazolium group covalently attached through a chain at the complex. The resulting complex is soluble in 1-butyl-3-methylimidazolium ionic liquid (bmimPF6) and not extractable by ether. The catalytic activity of this palladium complex in bmimPF6 is, however, unsatisfactory and only increases marginally in bmimPF6/supercritical CO2. This limitation has been overcome by supporting this imidazolium palladium complex on high surface area Al/MCM-41 aluminosilicate, whereby a solid active catalyst for the Suzuki cross-coupling has been obtained. Reusability and stability over reuse for this Al/MCM-41-supported catalyst have been studied. Graphical abstract.
Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone
Xia, Hongyu,Wang, Ganghu,Zhao, Dongbo,Zhu, Chunyin
supporting information, p. 922 - 929 (2022/02/10)
A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w
Rigid Multidimensional Alkoxyamines: A Versatile Building Block Library
Matt, Yannick,Wessely, Isabelle,Gramespacher, Lisa,Tsotsalas, Manuel,Br?se, Stefan
supporting information, p. 239 - 245 (2020/12/17)
Since the discovery of the “living” free-radical polymerization, alkoxyamines were widely used in nitroxide-mediated polymerization (NMP). Most of the known alkoxyamines bear just one functionality with only a few exceptions bearing two or more alkoxyamine units. Herein, we present a library of novel multidimensional alkoxyamines based on commercially available, rigid, aromatic core structures. A versatile approach allows the introduction of different sidechains which have an impact on the steric hindrance and dissociation behavior of the alkoxyamines. The reaction to the alkoxyamines was optimized by implementing a mild and reliable procedure to give all target compounds in high yields. Utilization of biphenyl, p-terphenyl, 1,3,5-triphenylbenzene, tetraphenylethylene, and tetraphenyl-methane results in linear, trigonal, square planar, and tetrahedral shaped alkoxyamines. These building blocks are useful initiators for multifold NMP leading to star-shaped polymers or as a linker for the nitroxide exchange reaction (NER), to obtain dynamic frameworks with a tunable crosslinking degree and self-healing abilities.
Electrochemical coupling halobenzene into biphenyl on a reusable Pd nanoparticle-coated carbon-paper electrode at ambient conditions
Wang, Chao-Nan,Lu, Yong-Heng,Liu, Yue,Liu, Jun,Yang, Yao-Yue,Zhao, Zhi-Gang
, p. 3997 - 4003 (2021/03/06)
Electrochemical organic synthesis (EOS) employing electrons to directly activate the reactants can readily complete the chemical conversion under mild conditions. Here, it presented an efficient electrochemical coupling halobenzene into biphenyl on a Pd nanoparticle-coated cathode. The biphenyl product can be obtained with a yield up to 77% at 35 mA, 6 h (3.9 F mol?1). In addition, after consecutive fifth run of the coupling reaction, the yield still remained atca.40%, suggesting its considerable recyclable capacity. In addition, the preliminary kinetics studyviathe off-line gas chromatography analysis of the reaction mixture shows a two-section reaction process, including the introduction process (IP) and fast conversion process (FCP). Further, the estimated reaction kinetics constant value of 0.196 min?1for FCP suggests a more effective conversion than that obtained by the previous study. This study adopts a simple way to fabricate a low-cost and reusable Pd electrode, achieving a high-efficiency electrochemical strategy for the Ullmann-type coupling reaction at mild conditions, and holds a great promise to extend this synthesis route to other important organic synthesis.
Pd-catalyzed oxidative homocoupling of arylboronic acids in WEPA: A sustainable access to symmetrical biaryls under added base and ligand-free ambient conditions
Appa, Rama Moorthy,Lakshmidevi, Jangam,Naidu, Bandameeda Ramesh,Venkateswarlu, Katta
, (2021/01/11)
Symmetrical and unsymmetrical biaryls comprises a diverse class of biologically eloquent organic compounds. We herein report, a quick and eco-friendly protocol for the synthesis of biaryls by an oxidative (aerobic) homocoupling of arylboronic acids (ABAs) using Pd(OAc)2 in water extract of pomogranate ash (WEPA) as an efficient agro-waste(bio)-derived aqueous (basic) media. The reactions were executed at ambient aerobic conditions in the absence of external base and ligand to result symmetrical biaryls in excellent yields. The use of renewable media with an effective exploitation of waste, short reaction times, excellent yields of products, easy separation of the products, unnecessating the external base, oxidant, ligand or volatile organic solvents and ambient reaction conditions are the vital insights of the present protocol.
Ultrafine and Highly Dispersed Pd/SiO2 for Suzuki?Miyaura Cross-coupling Reactions
Fan, Xizheng,Yang, Jingyi,Pang, Qingqing,Liu, Zhongyi,Zhang, Panke,Yang, Jing-He
, p. 2291 - 2301 (2021/01/04)
Abstract: Construction of heterogeneous Pd/SiO2 catalyst via the pollution-free strategy marked strong electrostatic adsorption has been reported for the application to Suzuki–Miyaura cross-coupling reactions. The exposed negatively charged oxygen groups, which were converted from the hydroxyl groups on the surface of silica under the alkaline atmosphere, could effectively anchor palladium species to form ultrafine Pd nanoparticles (Pd NPs) with an average particle size of 1.3?nm and high dispersion (43%). Pd/SiO2 catalyst was endowed with the excellent catalytic performance which was that the yield of the Suzuki–Miyaura reaction between bromobenzene and phenylboronic acid at 40?°C was > 99% for 30?min and the TOF was ~ 80,000?h?1. The catalyst could be easily recovered and recycled by facile procedure without a significant decrease in catalytic activity, which was able to maintain the 90% yield after repeated for 8 times. In addition, a continuous flow reaction device was designed using the Pd/SiO2 catalyst to effectively improve the production efficiency of biphenyl. Graphic Abstract: Pd/SiO2 catalyst constructed with the strategy of strong electrostatic adsorption (SEA) possesses uniformly dispersed and highly exposed Pd sites which can be easily transformed into electron-deficient Pdδ+ and strengthened stability for itself due to its strong interaction with the front surface of the carrier, and has been endowed the outstanding catalytic performance for Suzuki?Miyaura cross-coupling reaction. [Figure not available: see fulltext.]
Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Coupling of Two sp 2-Hybridized Organohalides
Li, Yuqiang,Yin, Guoyin
, p. 1657 - 1661 (2021/09/13)
Cross-coupling reactions are essential for the synthesis of complex organic molecules. Here, we report a nickel-catalyzed Ullmann cross-coupling of two sp 2-hybridized organohalides, featuring high cross-selectivity when the two coupling partners are used in a 1:1 ratio. The high chemoselectivity is governed by the bathocuproine ligand. Moreover, the mild reductive reaction conditions allow that a wide range of functional groups are compatible in this Ullmann cross-coupling.
