74683-29-7Relevant academic research and scientific papers
Ligand-free Cu(ii)-catalyzed aerobic etherification of aryl halides with silanes: An experimental and theoretical approach
Ahmed, Muhammad Naeem,Ahmad, Khalil,Yasin, Khawaja Ansar,Farooq, Tayyaba,Khan, Bilal Ahmad,Roy, Soumendra K.
, p. 11316 - 11333 (2019/07/31)
Owing to their wide occurrence in nature and immense applications in various fields, the synthesis of aryl alkyl ethers has remained a focus of interest. In contrast to the conventional/traditional methods of etherification, herein, we have reported a more efficient method, which is better yielding and more general in application. The etherification of aryl halides by alkoxy/phenoxy silanes was catalyzed by copper acetate in the presence of cesium carbonate and oxygen in DMF at 145 °C. All the as-synthesized compounds were characterized via the 1H-NMR and 13C-NMR spectroscopic techniques. Density functional theory calculations using the B3LYP functional were performed to elucidate the reaction mechanism. The C-O coupling reaction between 2-nitroiodobenzene and tetramethoxysilane was used as a model reaction. The activation energy barriers for the generation of catalytic species (31.6 kcal mol-1) and the σ-bond metathesis (16.0 kcal mol-1), oxidative addition/reductive elimination (20.3 kcal mol-1), halogen atom transfer (19.2 kcal mol-1) and single electron transfer (SET) (29.5 kcal mol-1) mechanisms for the C-O coupling reaction were calculated. Calculations for the key reaction steps were repeated with the B3PW91, PBEH1PBE, wB97XD, CAM-B3LYP and mPW1LYP functionals. The formation of catalytic species via a single electron transfer reaction between tetramethoxysilane and copper acetate, formation of methoxy radicals and methoxylation of copper showed an overall energy barrier of 31.6 kcal mol-1, and therefore is the rate determining step.
Diphenyl ether derivatives occupy the expanded binding site of cyclohexanedione compounds at the colchicine site in tubulin by movement of the αT5 loop
Bueno, Oskia,Gargantilla, Marta,Estévez-Gallego, Juan,Martins, Solange,Díaz, J. Fernando,Camarasa, María-José,Liekens, Sandra,Pérez-Pérez, María-Jesús,Priego, Eva-María
, p. 195 - 208 (2019/03/28)
Microtubule targeting agents represent a very active arena in the development of anticancer agents. In particular, compounds binding at the colchicine site in tubulin are being deeply studied, and the structural information recently available on this binding site allows structure-directed design of new ligands. Structural comparison of our recently reported high resolution X-Ray structure of the cyclohexanedione derivative TUB075 bound to tubulin and the tubulin-DAMA-colchicine complex has revealed a conformational change in the αT5 loop. By a grid-based computational analysis of the tubulin-DAMA-colchicine binding site, we have identified a new favourable binding area in the colchicine-site that was unexplored by our lead TUB075. Thus, based on a structure-guided design, new cyclohexanedione derivatives have been synthesized and tested for tubulin binding and in cellular assays. As a result, we have identified diphenyl ether derivatives with IC50 values around 10–40 nM against three different tumor cell lines and affinity constants for tubulin similar to that of colchicine around 107 M?1. As expected, they halted the cell cycle progression at G2/M phase at concentrations as low as 0.08 μM.
Synthesis of near-infrared fluorescent rhodamines via an SNArH reaction and their biological applications
Wang, Qing,Huang, Kun,Cai, Songtao,Liu, Chang,Jiao, Xiaojie,He, Song,Zhao, Liancheng,Zeng, Xianshun
supporting information, p. 7163 - 7169 (2018/10/24)
Near-infrared (NIR) dyes are of great interest in biomedicine due to diminished interfering absorption and fluorescence from biological samples, reduced scattering, and enhanced tissue penetration depth. In this context, we report the synthesis of rectili
Additivity of substituent effects in aromatic stacking interactions
Hwang, Jungwun,Li, Ping,Carroll, William R.,Smith, Mark D.,Pellechia, Perry J.,Shimizu, Ken D.
supporting information, p. 14060 - 14067 (2015/01/08)
The goal of this study was to experimentally test the additivity of the electrostatic substituent effects (SEs) for the aromatic stacking interaction. The additivity of the SEs was assessed using a small molecule model system that could adopt an offset face-to-face aromatic stacking geometry. The intramolecular interactions of these molecular torsional balances were quantitatively measured via the changes in a folded/unfolded conformational equilibrium. Five different types of substituents were examined (CH3, OCH3, Cl, CN, and NO2) that ranged from electron-donating to electron-withdrawing. The strength of the intramolecular stacking interactions was measured for 21 substituted aromatic stacking balances and 21 control balances in chloroform solution. The observed stability trends were consistent with additive SEs. Specifically, additive SE models could predict SEs with an accuracy from ±0.01 to ±0.02 kcal/mol. The additive SEs were consistent with Wheeler and Houk's direct SE model. However, the indirect or polarization SE model cannot be ruled out as it shows similar levels of additivity for two to three substituent systems, which were the number of substituents in our model system. SE additivity also has practical utility as the SEs can be accurately predicted. This should aid in the rational design and optimization of systems that utilize aromatic stacking interactions.
4-Hydroxy-2'-nitrodiphenyl ether analogues as novel tyrosinase inhibitors
Sapkota, Kiran,Lee, Eunyoung,Yang, Jae-Ho,Kwon, Youngjoo,Choi, Jongwon,Na, Younghwa
experimental part, p. 1319 - 1325 (2010/09/18)
Tyrosinase ubiquitously existing from microorganisms to animals and plants is known to be the most critical and rate limiting enzyme during melanin biosynthesis. In order to develop new tyrosinase inhibitor we have synthesized 14 diphenyl ether compounds
Synthesis of 1-amino-1,2,3,14b-tetrahydro-4H-pyrido[1,2-d]dibenzo[b,f] [1,4]oxazepine and related compounds
Caulfield, Wilson L.,Gibson, Samuel,Rae, Duncan R.
, p. 545 - 553 (2007/10/03)
The synthesis is described of the epimeric 1-amino-1,2,3,14b-tetrahydro-4H-pyrido[1,2-d]dibenzo[b,f]-[1,4]oxazepines 2 and their N-substituted analogues. The cis-amines 33, 36 and 38 were prepared from the ketone 31 by reduction of the corresponding oxime
TETRAZOLE DERIVATIVES AND DRUGS
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, (2008/06/13)
A compound of the formula [I] useful for treating allergic symptoms, cardiovascular disorders, cerebrovascular disorders, inflammation or other conditions mediated by SRS-A in humans and animals is disclosed. STR1
A NEW SYNTHESIS OF 3H-PHENOXAZIN-3-ONES
Bird, C. W.,Latif, M.
, p. 529 - 534 (2007/10/02)
The reductive cyclisation of 3-hydroxy-2'-nitrodiphenyl ethers provides a new synthesis of 3H-phenoxazin-3-ones, which should be particularly suitable for the synthesis of actinomycins.
