- Molecular structures, DFT studies and their photophysical properties in solution and solid state. Microwave-assisted multicomponent synthesis of organotin bearing Schiff bases
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A couple of luminescent organotin compounds derivated from ligands-ONO were obtained by multicomponent microwave assisted synthesis in short time (15 min) and good yields: ((E)-8, 8-8-diphenylbenzo[d] naphtho [1,2-h][1,3,6,2] dioxazastannonine (1) and (E)
- Cantón-Díaz, Arelly M.,Mu?oz-Flores, Blanca M.,Moggio, Ivana,Arias, Eduardo,Turlakov, Gleb,Del Angel-Mosqueda, Casiano,Ramirez-Montes, Pedro I.,Jiménez-Pérez, Víctor M.
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- Reactions of isomeric 3,6- and 3,5-di-tert-butyl-ortho-benzoquinones
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The interaction of 3,6-di-tert-butyl-ortho-benzoquinone (1) and 3,5-di-tert-butyl-ortho-benzoquinone (2) with NH3 in water-alcohol medium and with (NH4)2 CO3 in a solid phase has been studied.Redox processes with participation of a nucleophile of the medi
- Vol'eva, V. B.,Prokof'eva, T. I.,Prokof'ev, A. I.,Belostotskaya, I. S.,Komissarova, N. L.,Ershov, V. V.
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Read Online
- Fluorescent Molecular Rotors of Organoboron Compounds from Schiff Bases: Synthesis, Viscosity, Reversible Thermochromism, Cytotoxicity, and Bioimaging Cells
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We report the design, synthesis, and characterization of two new fluorescent molecular rotors of boron derived from Schiff bases: (2,4,8,10-tetra-tert-butyl-6-phenyldibenzo[d,h][1,3,6,2]dioxazaboronine (3) and 1,4-bis(2,4,8,10-tetra-tert-butyldibenzo[d,h][1,3,6,2]dioxazaboronin-6-yl)benzene (4), as well as the free ligand 2-[[(3,5-di-tert-butyl-2-hydroxyphenyl)imino]methyl]-4,6-di-tert-butylphenol 1. All compounds were fully characterized by NMR (1H,11B, and13C), IR, UV/vis, fluorescence spectroscopy, and high-resolution mass spectrometry. The crystal structures of 3 and 4 showed tetracoordinated boron atoms with semiplanar skeleton ligands. The free rotation of the fluorescent molecular rotor, only observed in the binuclear compound, was decreased with increasing viscosity, while the quantum yield was increased. Interestingly, the property of reversible thermochromism was found in organoboron 4 in the solid state. DFT calculations to determine the both complexes have free rotation around the CPh-B1 bond. The boron compounds 3 and 4 have shown low cytotoxicity activity in cell line A-431 and low green staining in cells.
- Ibarra-Rodr??guez, Marisol,Mu?oz-Flores, Blanca M.,Dias, H. V. Rasika,Sánchez, Mario,Gomez-Trevi?o, Alberto,Santillan, Rosa,Farfán, Norberto,Jiménez-Pérez, Víctor M.
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Read Online
- Tridentate [ONO] tungsten coordination compound and optical application thereof
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The invention provides a tridentate [ONO] tungsten coordination compound and optical application thereof, and the tridentate [ONO] tungsten coordination compound is divided into but not limited to three structures, namely a structure I, a structure II and
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Paragraph 0027-0030
(2021/05/29)
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- Metal-Free Oxidative Condensation of Catechols, Aldehydes and NH4OAc towards Benzoxazoles
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Benzoxazoles extensively exist in biologically active compounds, natural products, pharmaceuticals and functional materials. Thus, facile and green synthesis of such valuable compounds from easily available substrates will make a contribution to drug, material, and fine chemistry. A method for the synthesis of benzoxazoles from catechols, aldehydes and ammonium acetate is developed using NaIO4 as oxidant under metal- and additive-free conditions. A broad range of benzoxazoles including some fluorescent whitening agents, JTP-426467 and tafamidis analogues are synthesized in 56–95% yields with outstanding functional group tolerance. Mechanistic investigations suggest that an interesting o-iminocyclohexa-diene alcohol intermediate is involved in the reaction. These salient features of the protocol make it an alternative for the synthesis of benzoxazoles. (Figure presented.).
- Dong, Jianyu,Geng, Furong,Su, Lebin,Wu, Shaofeng,Yin, Shuang-Feng,Zhou, Dan,Zhou, Yongbo
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supporting information
p. 3607 - 3614
(2021/07/28)
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- Controllable synthesis of 2- And 3-aryl-benzomorpholines from 2-aminophenols and 4-vinylphenols
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We present herein a method for the controllable synthesis of 3-aryl-benzomorpholine and 2-aryl-benzomorpholine cycloadducts via cross-coupling/annulation between electron-rich 2-aminophenols and 4-vinylphenols. Molecular oxygen was successfully used in the reaction as the terminal oxidant and the complete inversion of chemoselectivity was achieved by the adjustment of the solvents and bases at room temperature.
- Dong, Kui,Jin, Xiao-Ling,Chen, Shihao,Wu, Li-Zhu,Liu, Qiang
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supporting information
p. 7941 - 7944
(2020/08/14)
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- A new bis-phenolate mesoionic carbene ligand for early transition metal chemistry
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We report the synthesis of a new pincer-type triazolylidene ligand precursor H3L[Cl] with redox-active 3,5-di-tert-butylphenolate substituents on a multigram scale following a converging ten-step route. The potential of this new mesoionic carbe
- Baltrun, Marc,Watt, Fabian A.,Schoch, Roland,W?lper, Christoph,Neuba, Adam G.,Hohloch, Stephan
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p. 14611 - 14625
(2019/10/16)
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- Synthesis of Mono- and Dinuclear Vanadium Complexes and Their Reactivity toward Dehydroperoxidation of Alkyl Hydroperoxides
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Several vanadium(V) complexes with either dipic-based or Schiff base ligands were synthesized. The complexes were fully characterized by elemental analysis, IR, 1H, 13C, and 51V NMR spectroscopy, as well as mass spectrometry and X-ray diffraction. Furthermore, they were tested toward their catalytic deperoxidation behavior and a significant difference between 4-heptyl hydroperoxide and cyclohexyl hydroperoxide was observed. In the case of 4-heptyl hydroperoxide, the selectivity toward the corresponding ketone was higher than with cyclohexyl hydroperoxide. DFT calculations performed on the vanadium complex showed that selective decomposition of secondary hydroperoxides with vanadium(V) to yield the corresponding ketone and water is indeed energetically feasible. The computed catalytic path, involving cleavage of the O-O bond, hydrogen transfer, release of ketone/water, and finally addition of hydroperoxide, can proceed without the generation of radical species.
- Schmidt, Anna-Corina,Hermsen, Marko,Rominger, Frank,Dehn, Richard,Teles, Joaquim Henrique,Sch?fer, Ansgar,Trapp, Oliver,Schaub, Thomas
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supporting information
p. 1319 - 1332
(2017/02/15)
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- Improvement in Aluminum Complexes Bearing Schiff Bases in Ring-Opening Polymerization of ?-Caprolactone: A Five-Membered-Ring System
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A series of five- and six-membered-ring Al complexes bearing Schiff bases was synthesized and their application to the ring-opening polymerization of ?-caprolactone (CL) was studied. The five-membered-ring Al complexes have been shown to have a significan
- Lee, Chieh-Ling,Lin, Ya-Fan,Jiang, Man-Ting,Lu, Wei-Yi,Vandavasi, Jaya Kishore,Wang, Li-Fang,Lai, Yi-Chun,Chiang, Michael Y.,Chen, Hsuan-Ying
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p. 1936 - 1945
(2017/06/13)
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- Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
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The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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Paragraph 0517
(2015/09/22)
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- Intramolecular redox-active ligand-to-substrate single-electron transfer: Radical reactivity with a palladium(II) complex
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Coordination of the redox-active tridentate NNO ligand LH2 to PdII yields the paramagnetic iminobenzosemiquinonato complex 3. Single-electron reduction of 3 yields diamagnetic amidophenolato complex 4, capable of activating aliphatic azide 5. Experimental and computational studies suggest a redox-noninnocent pathway wherein the redox-active ligand facilitates intramolecular ligand-to-substrate single-electron transfer to generate an open-shell singlet nitrene-substrate radical, ligand radical , enabling subsequent radical-type C-H amination reactivity with PdII.
- Broere, Dani?l L. J.,De Bruin, Bas,Reek, Joost N. H.,Lutz, Martin,Dechert, Sebastian,Van Der Vlugt, Jarl Ivar
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supporting information
p. 11574 - 11577
(2014/11/07)
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- Highly thermally stable eight-coordinate dichloride zirconium complexes supported by tridentate [ONN] ligands: Syntheses, characterization, and ethylene polymerization behavior
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A series of novel eight-coordinate dichloride zirconium complexes with the general formula L2ZrCl2 supported by two tridentate [ONN] ligands have been synthesized by the reaction of ZrCl4·2THF with 2 equiv of the correspon
- Li, Aike,Ma, Haiyan,Huang, Jiling
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p. 7460 - 7469
(2014/04/03)
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- A N-aryloxy-β-diketiminate ligand in 4d, 4f and 5f-metals complexes
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A new class of functionalized β-diketiminate ligands has been prepared from commercially available reagents. The novel N-aryloxy-β-diketiminate ligand proves to be an excellent ligand to support 4d, 4f and 5f metal ions.
- Dulong, Florian,Bathily, Oumou,Thuery, Pierre,Ephritikhine, Michel,Cantat, Thibault
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supporting information
p. 11980 - 11983
(2013/03/13)
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- Design of new arylamino-2-ethane-1,1-diyl- and benzoxazole-2-methylene- bisphosphonates vs cytotoxicity and chronic inflammation diseases. from hydrophobicity prediction to synthesis and biological evaluation
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A general synthetic approach to two new series of methylenebisphosphonates: arylamino-2-ethane-1,1-diyl- and benzoxazole-2-methylenebisphosphonates is presented. Acid hydrolysis of selected BPs was undertaken to give the corresponding bisphosphonic acid (
- Abdou, Wafaa M.,Barghash, Reham F.,Sediek, Ashraf A.
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p. 362 - 372
(2013/01/15)
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- COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
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The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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- MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR
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The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating diseases using such CFTR modulators.
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Page/Page column 72; 73
(2010/07/08)
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- Synthesis, X-ray structure and reactivity of a sterically protected azobisphenol ligand: On the quest for new multifunctional active ligands
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Different synthetic routes have been explored for the synthesis of the sterically protected 2,2′-dihydroxy-4,3,4,3′-tetra-tert- butylazobenzene ligand (2), which is an excellent candidate for the development of valence tautomeric complexes. As expected, s
- Evangelio, Emi,Saiz-Poseu, Javier,Maspoch, Daniel,Wurst, Klaus,Busque, Felix,Ruiz-Molina, Daniel
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scheme or table
p. 2278 - 2285
(2009/02/08)
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- Synthesis and antimicrobial evaluation of new 2-substituted 5,7-di-tert-butylbenzoxazoles
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Various synthetic pathways of the 30 novel 2-substituted 5,7-di-tert-butylbenzoxazoles as new potential antimicrobial drugs are discussed. The 28 intermediates are described as well. The compounds were characterized by 1H and 13C NMR spectra, MS spectra, IR/UV spectra and by means of CHN analysis. The purity of the final compounds was checked by HPLC and their lipophilicity (log K) was also determined by means of RP-HPLC. In the present study, the correlation between RP-HPLC retention parameter log K (the logarithm of capacity factor K) and various calculated log P data is shown. The target compounds were tested for their in vitro antimycobacterial activity. Several compounds showed antituberculotic activity comparable with or higher than the standard isoniazide. In vitro cytotoxicity testing of the most active benzoxazoles and isoniazide as a reference drug was performed using MTT assay and compared with isoniazide as a reference drug. Structure-activity relationships among the chemical structures, the physical properties and the biological activities of the evaluated compounds are discussed in the article.
- Vinsova, Jarmila,Cermakova, Katerina,Tomeckova, Alexandra,Ceckova, Martina,Jampilek, Josef,Cermak, Pavel,Kunes, Jiri,Dolezal, Martin,Staud, Frantisek
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p. 5850 - 5865
(2007/10/03)
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- New chiral ligands from myrtenal and caryophyllene for asymmetric oxydation of sulfides catalyzed by metal complexes
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From myrtenal and caryophyllene, widespread terpene compounds, three new chiral Schiff bases were prepared suitable for ligands in vanadium ions catalyzed sulfides oxidation to chiral sulfoxides.
- Khomenko,Salomatina,Kurbakova,Il'ina,Volcho,Komarova,Korchagina,Salakhutdinov,Tolstikov
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p. 1653 - 1661
(2007/10/03)
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- Direct asymmetric aldol reaction catalyzed by simple prolinamide phenols
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Simple prolinamides 1a-f were synthesized, and their catalytic effects on the direct asymmetric aldol reactions in organic solvents and in water were evaluated. Prolinamide phenols 1a-d were found to be effective catalysts for the reaction of aromatic ald
- Fu, Yu-Qin,Li, Zai-Chun,Ding, Li-Na,Tao, Jing-Chao,Zhang, Sheng-Hong,Tang, Ming-Sheng
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p. 3351 - 3357
(2007/10/03)
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- Highly Lipophilic Benzoxazoles with Potential Antibacterial Activity
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A series of lipophilic 2-substituted 5,7-di-tert-butylbenzoxazoles was prepared in average yields by the reaction of 3,5-di-tert-butyl-1,2-benzoquinone with amino acids and dipeptides bearing N-terminal glycine. Dipeptides having other N-terminal amino acids undergo oxidative deamination. 5,7-Di-tert-butylbenzoxazoles have shown activity against Mycobacterium tuberculosis and some nontuberculous strains where isoniazid has been inactive. Antifungal activity was mediocre.
- Vinsova, Jarmila,Horak, Vaclav,Buchta, Vladimir,Kaustova, Jarmila
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p. 760 - 770
(2007/10/03)
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- Synthesis and properties of 11-(3,5-di-tert-butyl-2-hydroxyphenylcarbamoyl)undecanoic acid, a new amphiphilic antioxidant
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Based on the membrane addressing concept, designing and synthesis of 11-(3,5-di-tert-butyl-2-hydroxyphenylcarbamoyl)undecanoic acid have been carried out. Antioxidant properties of the prepared compound were investigated in comparison with its non-amphiphilic analogues.
- Lodyato, Vladimir I.,Yurkova, Irina L.,Sorokin, Viktor L.,Shadyro, Oleg I.,Dolgopalets, Vladimir I.,Kisel, Mikhail A.
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p. 1179 - 1182
(2007/10/03)
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- Synthesis and ethylene polymerization behavior of a new titanium complex having two imine-phenoxy chelate ligands
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A novel (N-benzylidene-2-hydroxy-3,5-di-t-butyl-ani-line)2TiCl2 complex was synthesized and investigated for its potential as an ethylene polymerization catalyst in the presence of MAO or Ph3C+B-(Csu
- Suzuki, Yasuhiko,Kashiwa, Norio,Fujita, Terunori
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p. 358 - 359
(2007/10/03)
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- New hexacyclic binuclear tin complexes derived from bis-(3,5-di-tert-butyl-2-phenol)oxamide
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The syntheses of bis-(3,5-di-tert-butyl-2-phenol)oxamide (2a) and four new hexacyclic bimetallic tin compounds derivatives are reported: bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis(dibutyltin) (3), bis-(3,5-di-tert-butyl-2-oxo-phenyl)-oxamido-bis-(di
- Jímenez-Pérez, Victor M.,Camacho-Camacho, Carlos,Güizado-Rodríguez, Marisol,N?th, Heinrich,Contreras, Rosalinda
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p. 283 - 293
(2007/10/03)
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- 2-bromo-2-nitropropane/zn promoted reductive cyclizations of ortho-carbonyl, imino, or azo substituted nitrobenzenes
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Under the mild conditions, reductive cyclizations of 2-nitrobenzaldehydes, 2'-nitroacetophenone, and N-(2-nitrobenzylidene)anilines were accomplished in the presence of 2-bromo-2-nitropropane/Zn in methanolic solution. Under the similar conditions in MeOH/CH2Cl2, o-nitro-substituted phenylazobenzenes have been converted into 2-aryl-2H-benzotriazoles via reductive cyclizations that are widely used as UV absorbers. Synthesis and mechanistic details are discussed.
- Kim, Byeong Hyo,Lee, Yoon Seok,Kwon, Woong,Jin, Youngoo,Tak, Jung Ae,Jun, Young Moo,Baik, Woonphil,Lee, Byung Min
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p. 2581 - 2592
(2007/10/03)
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- SPONTANEOUS REARRANGEMENT IN COREY'S REACTION
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A (1)H-NMR study of the oxidative deamination of sec-alkyl primary amines with 3,5-di-tert-butyl-1,2-benzoquinone confirmed spontaneous rearrangement of the quinone-imines to the respective aromatic Schiff bases.
- Klein, Robert F. X.,Bargas, Lisa M.,Horak, Vaclav,Navarro, Mirtha
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p. 851 - 852
(2007/10/02)
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- Cyclodienones. Part 6. Preparation of 4-Azido-2,4,6-tri-t-butylcyclohexa-2,5-dienone and its Thermal, Photo-, and Acid-catalyzed Decomposition
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Preparation of 4-azido-2,4,6-tri-t-butylcyclohexa-2,5-dienone (3) from 4-bromo-2,4,6-tri-t-butylcyclohexa-2,5-dienone (1) and sodium azide is described.Treatment of (3) with concentrated sulphuric acid afforded 2,6-di-t-butyl-p-benzoquinone (7) in 75percent yield, while the reaction at -10 deg C in chloroform solution gave a tri-t-butylazepinone (5) and 3,5-di-t-butyl-o-benzoquinone (8).Photolysis of (3) in benzene afforded 2,4-di-t-butylcyclopenta-2,4-dienone (11), which was isolated as the dimer (12).Thermolysis of (3) in boiling toluene gave 6-amino-2,4-di-t-butylphenol (17), 2,4,6,8-tetra-t-butyl-1H-phenoxazin-1-one (21), and 2-cyano-9,9a-dihydro-3,5,7,9a-tetra-t-butylcyclopentabenzoxazin-1(3aH)-one (22) in 15, 15 and 48percent yields, respectively.When the thermolysis was carried out with very low reagent concentrations, 5-cyano-2,4-di-t-butylcyclopenta-2,4-dienone (23), in addition to the phenol (17), was obtained.The compound (23) was also obtained by thermolysis of (3) in boiling acetic anhydride and in boiling toluene containing acetic anhydride.The reaction pathway for the formation of compounds (17), (22), and (23) on thermolysis of the azide (3) is also discussed.
- Fukata, Gouki,Sakamoto, Naoya,Tashiro, Massashi
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p. 2841 - 2848
(2007/10/02)
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- CYCLOHEXADIENONES. 3. PREPARATION AND THERMAL DECOMPOSITION OF 4-AZIDO-2,4,6-TRI-t-BUTYL-2,5-CYCLOHEXADIEN-1-ONE
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Reaction of 4-bromo-2,4,6-tri-tert-butyl-2,5-cyclohexadien-1-one (1) with sodium azide was carried out in DMF to afford 4-azido-2,4,6,-tri-tert-butyl-2,5-cyclohexadien-1-one (4) in 85percent yield.Thermal decomposition of 4 in boiling toluene gives 6-amino-2,4-di-tert-butylphenol (5), 2,4,6,8-tetra-tert-butylphenoxazin-1-one (7) and 2,4,6,8a-tetra-tert-butyl-7-cyano-8-oxo-5a,8a-dihydrocyclopentenobenzoxazine (8).However, the termal decomposition of 4 was carried out under highly diluted conditions to afford 5 and 2,4-di-tert-butyl-5-cyano-2,4-cyclopentadien-1-one (9)in 48 and 50percent yields, respectively.It was also found that the thermal decomposition of 4 in boiling toluene in the presence of acetic anhydride afforded 6-acetoamido-2,4-di-tert-butylphenol (6) and 9 in 47 and 50percent yields, respectively.The reaction pathways of the formation of 5, 8 and 9 were proposed in the present paper.
- Fukata, Gouki,Sakamoto, Naoya,Tashiro, Masashi
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p. 1259 - 1264
(2007/10/02)
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