- Synthesis and biological evaluation of disubstituted amidoxanthones as potential telomeric G-quadruplex DNA-binding and apoptosis-inducing agents
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A series of disubstituted xanthones was obtained by cationic modification of xanthone's C2 and C7 with amine groups of different pKa values. Modified structures by using moieties with high pKa values had good antitumor activity according to the MTT assay, AO/EB staining and flow cytometry assay, especially bis-dimethylamine derivative (5a). Further study indicated that compound 5a had good binding activity to telomeric G-quadruplex DNA, as detected by using spectroscopy methods, melting profiles, polymerase chain reaction stop assay and molecular modeling study. The results suggested that the antitumor activity of 5a might be associated with its stabilization of G-quadruplex DNA, which could be developed as new G-quadruplex DNA stabilizer and potent antitumor agents.
- Shen, Rui,Chen, Yujiao,Li, Ziqian,Qi, Hui,Wang, Yitian
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Read Online
- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention relates to a compound for an organic electronic element. To the present invention, an organic electronic element having high luminous efficiency, low driving voltage, and high heat resistance can be provided, and color purity and lifetime of the organic electronic element can be improved.
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Paragraph 0372-0375
(2021/03/23)
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- COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF
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The present invention provides a compound represented by chemical formula 1, an organic electric device including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the organic electric device. By including the compound represented by chemical formula 1 in the organic material layer, the driving voltage of the organic electric device can be lowered, luminous efficiency and lifespan can be improved, and in particular, the lifespan can be improved.COPYRIGHT KIPO 2021
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Paragraph 0144; 0238; 0271-0274
(2020/10/31)
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- Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation
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A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.
- Chang, Xihao,Zhang, Qinglin,Guo, Chang
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supporting information
p. 10 - 13
(2019/01/04)
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- Formal Aniline Synthesis from Phenols through Deoxygenative N-Centered Radical Substitution
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Phenolic, lignin-derived substrates have emerged as desirable biorenewable chemical feedstocks for coupling reactions. A radical-mediated conversion of phenol derivatives to anilines is reported, using unfunctionalized hydroxamic acids as the N-centered radical source. The applicability of this triethyl phosphite mediated O-atom transfer approach, which tolerates a range of steric and electronic demands to naturally occurring phenols and lignin models, has been demonstrated in this work to access the corresponding aniline derivatives.
- Lardy, Samuel W.,Luong, Kristine C.,Schmidt, Valerie A.
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supporting information
p. 15267 - 15271
(2019/12/11)
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- Preparation method of xanthydrol
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The invention relates to the chemical field, in particular to a preparation method of xanthydrol. The method comprises the steps as follows: 31.3 g of o-chlorobenzoic acid, 37.6 g of phenol, 5.53 g ofpotassium carbonate, 16.2 mL of pyridine, 2 g of copper powder, 2 g of cuprous iodide and 200 mL of water are added to a 500 mL three-neck flask, the mixture is stirred mechanically, subjected to reflux for 2 h and cooled to the room temperature, diluted hydrochloric acid is added to make a reaction solution to be acid, a solid is filtered out, washed and dissolved in a 10% sodium hydroxide aqueous solution, the obtained solution is added to a mixed solution of acetic acid and water for precipitation of a solid, the obtained solid is recrystallized with the mixed solution of acetic acid and water, and 36.4 g of white crystal o-phenoxybenzoic acid is obtained; 20 g of o-phenoxybenzoic acid and 80 mL of tetrahydrofuran are added to a 150 mL three-neck flask, the mixture is stirred mechanically and cooled to 0 DEG C, 23 mL of a catalyst is dropwise added at the temperature of 0 DEG C, the obtained mixture is heated for reflux for 30 min after addition and cooled to the room temperature,and ice water is added to a reaction solution. The technological process is simple and safe to operate, the production cost is reduced, environmental pollution is avoided in the reaction process, andthe product quality is improved.
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Paragraph 0008; 0009
(2018/03/26)
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- Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis
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We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.
- Wang, Shao-Feng,Cao, Xiao-Ping,Li, Yang
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p. 13809 - 13813
(2017/10/24)
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- A photoredox-neutral Smiles rearrangement of 2-aryloxybenzoic acids
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We report on the use of visible light photoredox catalysis for the radical Smiles rearrangement of 2-aryloxybenzoic acids to obtain aryl salicylates. The method is free of noble metals and operationally simple and the reaction can be run under mild batch or flow conditions. Being a redox neutral process, no stoichiometric oxidants or reductants are needed.
- Gonzalez-Gomez, Jose C.,Ramirez, Nieves P.,Lana-Villarreal, Teresa,Bonete, Pedro
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supporting information
p. 9680 - 9684
(2017/11/30)
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- Carboxyl radical-assisted 1,5-aryl migration through Smiles rearrangement
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We report herein, a silver(i)-catalyzed Smiles rearrangement of 2-aryloxy- or 2-(arylthio)benzoic acids to provide aryl-2-hydroxybenzoate or aryl-2-mercaptobenzoate dimer, respectively, through 1,5-aryl migration from oxygen or sulfur to carboxylate oxygen. Mechanistically, the aryl ether moiety undergoes an intramolecular ipso attack by the carboxyl radical followed by a C-O or C-S bond cleavage. Aryl-2-mercaptobenzoates undergo oxidative dimerization through a thiol moiety in situ.
- Hossian, Asik,Jana, Ranjan
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p. 9768 - 9779
(2016/10/31)
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- Copper-mediated direct aryloxylation of benzamides assisted by an N, O -bidentate directing group
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Copper-mediated selective mono- or diaryloxylation of benzamides has been achieved by using 2-aminopyridine 1-oxide as a new and removable N,O-bidentate directing group. The reaction system shows a broad substrate scope and provides a straightforward way for the synthesis of mono- and diaryloxylated benzoic acids.
- Hao, Xin-Qi,Chen, Li-Juan,Ren, Baozeng,Li, Liu-Yan,Yang, Xin-Yan,Gong, Jun-Fang,Niu, Jun-Long,Song, Mao-Ping
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supporting information
p. 1104 - 1107
(2014/03/21)
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- Fe3O4@mesoporouspolyaniline: A highly efficient and magnetically separable catalyst for cross-coupling of aryl chlorides and phenols
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A high surface, magnetic Fe3O4@mesoporouspolyaniline core-shell nanocomposite was synthesized from magnetic iron oxide (Fe 3O4) nanoparticles and mesoporouspolyaniline (mPANI). The novel porous magnetic Fe3O4 was obtained by solvothermal method under sealed pressure reactor at high temperature to achieve high surface area. The mesoporouspolyaniline shell was synthesized by in situ surface polymerization onto porous magnetic Fe3O4 in the presence of polyvinylpyrrolidone (PVP) and sodium dodecylbenzenesulfonate (SDBS), as a linker and structure-directing agent, through 'blackberry nanostructures' assembly. The material composition, stoichiometric ratio and reaction conditions play vital roles in the synthesis of these nanostructures as confirmed by variety of characterization techniques. The role of the mesoporouspolyaniline shell is to stabilize the porous magnetic Fe3O4 nanoparticles, and provide direct access to the core Fe3O4 nanoparticles. The catalytic activity of magnetic Fe3O 4@mesoporousPANI nanocomposite was evaluated in the cross-coupling of aryl chlorides and phenols. Copyright
- Arundhathi,Damodara,Likhar, Pravin R.,Kantam, M. Lakshmi,Saravanan,Magdaleno, Travis,Kwon, Sun Hee
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supporting information; experimental part
p. 1591 - 1600
(2011/08/03)
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- Kinetics of proton transfer between ortho substituted benzoic acids and the carbinol base of crystal violet in toluene. Ortho effect on the reactivity of benzoic acids in apolar aprotic solvents
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Apolar aprotic solvents are particularly advantageous for investigating the intrinsic ortho effect free from complications of specific solvent effects. A kinetic study for toluene-phase proton transfers between ortho F, Cl, Br, I, OMe, OEt, OPh, OAc, Me, NO2, COMe, COPh, OH, NH2, and H benzoic acids and crystal violet carbinol base has shown the forward rate constant (log k+1) is the most appropriate reactivity parameter in toluene. log k+1 (toluene) as compared to other reported reactivity parameters in benzene, toluene, or chlorobenzene has been found more sensitive to the ortho substituent effect. The regression results of the correlation of log k+1 (toluene) of the acids (except OH and NH2 substituted ones) according to seven ortho effect models are all very significant, and the best result is given by Fujita-Nishiokas model. The overall analysis reveals that a substituents ortho effect pattern is a 58:24:18 ratio of its ordinary electrical, proximity electrical, and steric effects and that the proximity electrical effect is the major component to account for the peculiarity of the substituents ortho effect. The results further favor the transmission of this effect mainly through the molecular cavity. The effect may, however, be outweighed by the steric component for bulky enough substituents, e.g., Me. The enhanced strength exhibited by salicylic acid in toluene has been quantitatively described using Pytela-Lisas δHB i parameter. The abnormally high log k+1 observed for anthranilic acid in toluene has been ascribed to a very extensive homoconjugation in its acid-acid anion complex induced by the acids three hydrogen bond donors.
- Sen Gupta, Susanta K.,Mishra, Sangeeta
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experimental part
p. 4616 - 4623
(2011/06/26)
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- Synthesis and cancer cell cytotoxicity of substituted xanthenes
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A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9g ([N,N-diethyl]-9-hydroxy-9-(3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC50 values ranging from 36 to 50 μM across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e.g., the incorporation of a 7-fluoro substituent to 9g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring.
- Giri, Rajan,Goodell, John R.,Xing, Chenguo,Benoit, Adam,Kaur, Harneet,Hiasa, Hiroshi,Ferguson, David M.
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experimental part
p. 1456 - 1463
(2010/04/29)
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- Synthesis, antitubercular activity and docking study of novel cyclic azole substituted diphenyl ether derivatives
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The re-emergence of tuberculosis (TB) as a global health problem over the past few decades, accompanied by the rise of drug-resistant strains of Mycobacterium tuberculosis, emphasizes the need for discovery of new therapeutic drugs against this disease. The emerging serious problem both in terms of TB control and clinical management prompted us to synthesize a novel series of heterocyclic o/m/p substituted diphenyl ether derivatives and determine their activity against H37Rv strain of Mycobacterium. All 10 compounds inhibited the growth of the H37Rv strain of mycobacterium at concentrations as low as 1 μg/mL. This level of activity was found comparable to the reference drugs rifampicin and isoniazid at the same concentration. Molecular modeling of the binding of the diphenyl ether derivatives on enoyl-ACP reductase, the molecular target site of triclosan, indicated that these compounds fit within the binding domain occupied by triclosan. Hence the diphenyl ether derivatives tested in this study were docked to ENR and the binding of the diphenyl ether derivatives was also estimated using a variety of scoring functions that have been compiled into the single consensus score. As the scores ranged from 47.27% to 65.81%, these bioactive compounds appear to have a novel mechanism of action against M. tuberculosis, and their structural features should be studied further for their potential use as new antitubercular drugs.
- Kini, Suvarna G.,Bhat, Anilchandra R.,Bryant, Byron,Williamson, John S.,Dayan, Franck E.
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experimental part
p. 492 - 500
(2009/08/07)
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- Microwave-assisted synthesis of 2-phenoxybenzoic acids
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Substituted 2-phenoxybenzoic acid derivatives were synthesised in high yield and in short reaction times using the Ullmann condensation of 2-chlorobenzoic acid with phenol derivatives under microwave irradiation in dry media.
- Pellon, Rolando F.,Martin, Ana,Mesa, Miriam,Docampo, Maite L.,Gomez, Victoria
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p. 527 - 529
(2007/10/03)
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- A convenient procedure for parallel ester hydrolysis
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The treatment of alkyl esters with barium hydroxide octahydrate in methanol followed by protonation with anhydrous hydrogen chloride affords carboxylic acids. The procedure does not require aqueous workup and is particularly suitable for parallel synthesis applications.
- Anderson, Marc O.,Moser, Jamie,Sherrill, John,Guy, R. Kiplin
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p. 2391 - 2393
(2007/10/03)
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- The use of ultrasound in the synthesis of 2-carboxy substituted diphenylethers using water as solvent
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An improved synthesis of 2-carboxy substituted diphenylethers using water as solvent can be achieved by ultrasound irradiation. A number of diphenylethers was prepared in good yields in a very short reaction time.
- Pellon Comdom, Rolando F.,Docampo Palacios, Maite L.
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p. 921 - 926
(2007/10/03)
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- Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of neurodegenerative diseases
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The invention relates to BCAT inhibitors and the use thereof for treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the overstimulation of the excitatory amino acids, treating anxiety, psychosis, convulsions, aminoglycoside antibiotics-induced hearing loss, migraine headache, chronic pain, neuropathic pain, Parkinson's disease, diabetic retinopathy, glaucoma, CMV retinitis, urinary incontinence, opioid tolerance or withdrawal, and inducing anesthesia, as well as for enhancing cognition.
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- Nucleophilic substitution in O-phenyldibenzofuranium and 10-phenylxanthonium cations
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Reactions of O-phenyldibenzofuranium tetrafluoroborate with nucleophiles (OH-, NO2-, AcO-) in aqueous media follow the SNAr-mechanism and involve dehydroarenes. In DMSO, this salt smoothly reacts with NO2- and I- with predominant opening of the furan ring. 10-Phenylxanthonium tetrafluoroborate readily arylates the NO2- ion in water (at the N and O atoms), mainly with predominant opening of the central ring, and is completely decomposed even with weak bases (NH2OH, 2,4-dinitrophenylhydrazine). The Baeyer -Villiger oxidation of this salt affords xanthone and 2-phenoxybenzoic acid.
- Tolstaya,Bobyleva,Vanchikov,Kovalysheva,Kulikov,Tsariev
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p. 789 - 797
(2007/10/03)
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- Carboxylic acid derivatives
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Carboxylic acid derivatives of the formula: STR1 are provided, which are useful for treatment of androgen dependent diseases.
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- Use of pyridine as cocatalyst for the synthesis of 2-carboxy substituted diphenylethers by Ullmann-Goldberg condensation
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The synthesis of 2-carboxy-diphenylethers from o-chloro-benzoic acid and phenols is reported using water as solvent and copper, cuprous iodide and pyridine as catalysts.
- Pellon,Carrasco,Milian,Rodes
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p. 1077 - 1083
(2007/10/02)
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- SULFURANYL RADICAL STRUCTURE AND REACTIONS OF o-(THIO)BENZOYLOXYL RADICALS FORMED BY THE DECOMPOSITION OF t-BUTYL o-(THIO)-PERBENZOATES STUDIED BY 1H AND 13C CIDNP AND 17O NMR.
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**1H and **1**3C CIDNP signals were observed in the methyl group of o-(methylthio)benzoic acid and the methylene group of 3,1-benzoxathian-4-one during the thermal decomposition of t-butyl o-(methylthio)perbenzoate. The results show that the free 'o-(methylthio)benzoyloxyl radical' itself is better represented as the bridged sulfuranyl radical in which most of the spin density is localized at the sulfur atom rather than in the carboxyl. Thermolysis of t-butyl o-(methylthio)- and o-(phenylthio)perbenzoates-carbonyl-**1**7O was carried out and the oxygen labels were detected by **1**7O NMR spectroscopy. The migration of phenyl group and the peroxomonosulfate oxidation of o-(phenylthio)benzoic acid are also discussed.
- Nakanishi,Kusuyama,Ikeda,Iwamura
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p. 3123 - 3128
(2007/10/02)
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