- An ether-linked halogenated phenazine-quinone prodrug model for antibacterial applications
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Antibiotic-resistant infections present significant challenges to patients. As a result, there is considerable need for new antibacterial therapies that eradicate pathogenic bacteria through non-conventional mechanisms. Our group has identified a series o
- Huigens, Robert W.,Jin, Shouguang,Kim, Young S.,Liu, Ke,Yang, Hongfen
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supporting information
p. 6603 - 6608
(2021/08/12)
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- PREPARATION AND USES OF REACTIVE OXYGEN SPECIES SCAVENGER DERIVATIVES
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Compounds of Formula (I) a or (I) b: including certain quinone derivatives, and the corresponding pharmaceutical compositions, which may serve to modulate ferroptosis in a subject. Also disclosed herein are the preparations of these compounds and pharmaceutical compositions and their potential uses in the manufacture of a medicament in reducing reactive oxygen species (ROS) in a cell and for preventing, treating, ameliorating certain related disorder or a disease.
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Page/Page column 83; 86
(2019/03/07)
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- Preparation method of trimethylhydroquinone
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The invention discloses a preparation method of trimethylhydroquinone. The preparation method is characterized in that isophorone is used as an initial raw material and oxidized into oxoisophorone, then an acylation reaction occurs in the oxoisophorone and an acylating agent to produce trimethyl hydroquinone diester, and the trimethyl hydroquinone diester is hydrolyzed to produce 2,3,5-trimethylhydroquinone. The method disclosed by the invention has cheap and easily-available raw materials and simple syntheses steps, a used solvent is easy to recover and reuse, and the method needs not use ofa big amount of acid and alkali, thereby reducing pollution of the environment, being convenient for large-scale industrial production and having good application prospects.
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Paragraph 0039; 0049; 0047; 0048; 0055; 0056; 0063; 0064
(2019/01/07)
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- SUBSTITUTED-p-QUINONE DERIVATIVES FOR TREATMENT OF OXIDATIVE STRESS DISEASES
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Methods of treating or suppressing oxidative stress diseases including mitochondrial diseases, impaired energy processing disorders, neurodegenerative diseases and diseases of aging are disclosed, as well as compounds useful in the methods of the invention, such as 2-substituted-p-quinone derivatives as disclosed herein.
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Paragraph 0170; 0194
(2018/10/15)
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- Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group
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1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an α-aryl group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey’s oxazaborolidine catalyst. Specifically, the TIPS nitronate with an α-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.
- Jiang, Minghui,Feng, Lifei,Feng, Juanjuan,Jiao, Peng
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supporting information
p. 2210 - 2213
(2017/05/12)
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- Highly stereoselective construction of the C2 stereocentre of α-tocopherol (Vitamin E) by asymmetric addition of Grignard reagents to ketones
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Tertiary alcohol precursors of both C2 diastereoisomers of α-tocopherol were prepared in three ways by our recently reported asymmetric Grignard synthesis. The versatility of Grignard chemistry inherent in its three-way disconnection was exploited to allow the synthesis of three product grades: 77:23 dr (5 steps), 81:19 dr (5 steps) and 96:4 dr (7 steps, one gram scale) from readily available and abundant starting materials. The products were converted to their respective α-tocopherols in 3 steps, which allowed a definitive re-assignment of their absolute configurations.
- Bieszczad, Bartosz,Gilheany, Declan G.
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p. 6483 - 6492
(2017/08/16)
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- QUINONE BASED NITRIC OXIDE DONATING COMPOUNDS
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The present invention relates to nitric oxide donor compounds having a quinone based structure, to processes for their preparation and to their use in the treatment and/or prophylaxis of glaucoma and ocular hypertension.
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Page/Page column 33; 34
(2015/11/18)
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- Total synthesis of (R, R, R)-γ-tocopherol through cu-catalyzed asymmetric 1,2-addition
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Based on the asymmetric copper-catalyzed 1,2-addition of Grignard reagents to ketones, (R, R, R)-γ-tocopherol has been synthesized in 36% yield over 12 steps (longest linear sequence). The chiral center in the chroman ring was constructed with 73% ee by the 1,2-addition of a phytol-derived Grignard reagent to an a-bromo enone prepared from 2,3-dimethylquinone.
- Wu, Zhongtao,Harutyunyan, Syuzanna R.,Minnaard, Adriaan J.
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supporting information
p. 14250 - 14255
(2015/03/18)
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- Hydrindacene-based acetylenic macrocycles with horizontally and vertically ordered functionality arrays
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The macrocyclization of 2,6-diethynyl hydrindacenes (1) with functional groups at mutually perpendicular positions results in the formation of novel macrocycles which, as a result of the hindered rotation of the hydrindacene units, possess directionally persistent peripheral functionalities. The two hydrindacene units in the dimer macrocycle (2) have been shown to interact electronically through their respective butadiyne moieties, whereas the trimer macrocycle (3) demonstrates a moderate degree of geometrical flexibility as a result of the five-membered hydrindacene rings. In addition, these trimer macrocycles contain a central cavity suitably sized for the inclusion of various solvent molecules. These new macrocycles can be further modified by introducing π-conjugated side groups, such as styryl and thienyl groups, as well as by attaching a variety of peripheral ester groups. Copyright
- Kawai, Hidetoshi,Utamura, Tatsuya,Motoi, Erina,Takahashi, Tomoko,Sugino, Hiroyoshi,Tamura, Manabu,Ohkita, Masakazu,Fujiwara, Kenshu,Saito, Takao,Tsuji, Takashi,Suzuki, Takanori
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p. 4513 - 4524
(2013/05/08)
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- Enzymatic substrates derived from phenoxazinone and their use as developer in detection of microorganisms with peptidase activity
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Novel enzymatic substrates of the general formula below: reaction media containing the same and their use for detecting and/or identifying and/or quantifying microorganisms expressing at least one peptidase activity.
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Page/Page column 15
(2009/12/07)
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- Synthesis and testing of chromogenic phenoxazinone substrates for β-alanyl aminopeptidase
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Novel 7-N-(β-alanyl)aminophenoxazin-3-one salts 27a-d have been synthesized and tested as chromogenic substrates for β-alanyl aminopeptidase, which is present in Pseudomonas aeruginosa, the most common respiratory pathogen in patients with cystic fibrosis. The biological results show that 7-N-(β-alanyl)amino-1-pentylphenoxazin-3-one trifluoroacetate salt 27a is a chromogenic substrate for this bacterium, with a low degree of diffusion in nutrient media for growing bacterial cultures and a bright red colour, making it easily distinguishable from the agar background. This journal is The Royal Society of Chemistry.
- Zaytsev, Andrey V.,Anderson, Rosaleen J.,Bedernjak, Alexandre,Groundwater, Paul W.,Huang, Yongxue,Perry, John D.,Orenga, Sylvain,Roger-Dalbert, Celine,James, Arthur
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p. XX682-692
(2008/09/17)
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- Tail variants of redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
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Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed,
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Page/Page column 15
(2010/11/26)
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- New Drug Delivery System for Crossing the Blood Brain Barrier
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New ubiquinol analogs are disclosed, as well as methods of using these compounds to deliver drug moieties to the body.
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Page/Page column 28-29
(2008/06/13)
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- Redox-active therapeutics for treatment of mitochondrial diseases and other conditions and modulation of energy biomarkers
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Methods of treating or suppressing mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), or Kearns-Sayre Syndrome (KSS) are disclosed,
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Page/Page column 37-38
(2010/11/25)
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- A new synthetic route to (S)-chroman aldehyde, a key chiral precursor of vitamin E
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A highly stereocontrolled synthetic route to (S)-chroman aldehyde has been developed which starts with trimethyl-p-hydroquinone and (R)-glycerladehyde acetonide and employs as key steps the Michael addition of the aromatic copper species onto the (R)-4-acryloyl-1,3-dioxolane followed by the highly diastereoselective methylation of the resulting ketone adduct.
- Mikoshiba,Mikami,Nakai
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p. 989 - 990
(2007/10/03)
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- Friedel-Crafts Benzylation of 1,4-Dialkoxybenzenes - Cleavage and Rearrangement of Esters and Methoxymethyl Ethers in ZnCl2 Montmorillonite K10 Clay
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Benzylation of p-dialkoxybenzenes can be achieved through the use of modified montmorillonite K10 clay. For the first time, synthese of nitro-diarylmethanes were obtained by Friedel-Crafts alkylation with good yields. In the case of p-methoxymethyl phenyl ether and phenyl ester, selectivity favoring Fries rearrangement over benzylation is reported.
- Waterlot, C.,Couturier, D.,Hasiak, B.
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p. 417 - 429
(2007/10/03)
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- An expeditious route to CoQ(n), Vitamins K1 and K2, and related allylated para-quinones utilizing Ni(0) catalysis
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Coupling reactions between vynylalanes and chloromethylated para-quinones, mediated by catalytic amounts of Ni(0), lead directly to allylated products, including coenzyme Q, and vitamins K1 and K2.
- Lipshutz, Bruce H.,Kim, Sung-Kyu,Mollard, Paul,Stevens, Kirk L.
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p. 1241 - 1253
(2007/10/03)
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- Enzymatic resolution for an improved enantioselective synthesis of benzofuranyl derivatives: Precursors to a class of vitamin E related antioxidants
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Enzymatic resolution of 3-hydroxymethylbenzofurans using Candida rugosa lipase provides an enantioselective synthesis of vitamin E related antioxidants.
- Ayers, Timothy A.,Schnettler, Richard A.,Marciniak, Gilbert,Stewart, Kenneth T.,Mishra, Rajesh K.,Krysan, Damian J.,Bernas, Bradley R.,Bhardwaj, Poonam,Fevig, Thomas L.
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- Selective nitration versus oxidative dealkylation of hydroquinone ethers with nitrogen dioxide
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Various alkyl-substituted p-dialkoxybenzenes (ArH) react readily with nitrogen dioxide (NO2) in dichloromethane solution via either nitration (ArNO2) or oxidative dealkylation to quinones (Q). Spectral transients indicate that these coupled processes proceed from the dialkoxybenzene radical cation (ArH+) formed as the common reactive intermediate from electron-transfer in the disproportionated precursor [ArH, NO+]NO3-. In fast subsequent steps, ArH+ undergoes homolytic coupling with NO2 (which leads to aromatic nitration) and nucleophilic attack of NO3- (which results in oxidative dealkylation). As such, the competition between nitration and oxidative dealkylation is effectively modulated by solvent polarity and added nitrate.
- Rathore,Bosch,Kochi
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p. 6727 - 6758
(2007/10/02)
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- Electroorganic Synthesis, 58. Synthesis of Substituted Benzoquinones and their Use for Mediated Electrochemical Conversions
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Hydroxy- (1a-3a) and hydroxyalkyl-substituted benzoquinones (6a-8a, 27a), suited to be immobilized by esterification with polyacrylic acid, are prepared.Their cathodic reduction potential Ep,c (1) correlates linearly with their substituent constant.The cathodic reduction of dioxygen and the palladium(II)-catalyzed anodic oxidation of alkenes are mediated by the benzoquinones 7b, 8b and 27b, respectively. - Key Words: Benzoquinones, substituted / Cyclic voltammetry / Cathodic dioxygen reduction, mediated / Anodic Wacker oxidation, mediated
- Riering, Helmut,Schaefer, Hans J.
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p. 859 - 874
(2007/10/02)
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- Oxidative Dealkylation of Hydroquinone Ethers with Nitrogen Dioxide in the Convenient Preparation of Quinones
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Various Hydroquinone dialkyl ethers (R2Q) are effectively converted by nitrogen dioxide into the corresponding quinone (Q) and alkyl nitrite (RONO) in dichloromethane at room temperature or below.The preparative procedure for the isolation of crystalline quinones in quantitative yield merely involves the convenient removal of the low boiling solvent in vacuo.Isotopic labelling studies demonstrate that the oxidative dealkylation proceeds via alkoxy scission of the labile cation radical (R2Q-cation radical) formed via the oxidation of the hydroquinone ether by nitrogen dioxide ( as the disproportionated ion pair NO+NO3-).The electron-transfer mechanism is confirmed by the spectral observation of R2Q-cation radical (identified by the isolation of the crystalline salt R2Q-cation radical-SbCl6-) and its rapid conversion into quinone and alkyl nitrite by combination with nitrate (NO3-) and nitric oxide (NO).
- Rathore, Rajendra,Bosch, Eric,Kochi, Jay K.
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p. 1157 - 1166
(2007/10/02)
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- SYNTHESIS AND SRN1 REACTION OF THE FIRST QUINONE-OXAZOLE BIOREDUCTIVE ALKYLATING AGENT
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2-(2-Chloromethyloxazol-5-yl)-3,5,6-trimethyl-1,4-benzoquinone, the first compound of a new quinone-heterocyclic class of bioreductive alkylating agent, was prepared from trimethylhydroquinone in 8 steps and reacted by SRN1 reaction with lithiu
- Crozet, Michel P.,Sabuco, Jean-Francois,Tamburlin, Isabelle,Barreau, Michel,Giraud, Luc,Vanelle, Patrice
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- SYNTHESIS OF DIQUINONE DERIVATIVES OF DEUTEROPORPHYRIN IX FOR THE STUDY OF THE FIRST STAGE IN THE PROCESS OF PHOTOSYNTHESIS
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Diquinone derivatives of deuteroporphyrin IX containing covalent bridges of different lengths between the chromophores have been synthesized.The compounds were prepared by the condensation of hydroxy-quinones with deuteroporphyrin IX using a mixed anhydri
- Borovkov, V. V.,Evstigneeva, R. P.,Makova, S. Z.
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p. 142 - 147
(2007/10/02)
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- S(RN)1 reactions of a tetrasubstituted-1,4-benzoquinone
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The C-alkylation reaction of 2-chloromethyl-3,5,6-trimethyl-1,4-benzoquinone by 2-nitropropane anion is shown to proceed by the S(RN)1 mechanism. This mechanism is confirmed by the inhibitory effects of dioxygen, p-dinitrobenzene, cupric chloride and di-t
- Crozet,Giraud,Sabuco,Vanelle,Barreau
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p. 4125 - 4128
(2007/10/02)
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- REACTION OF 1,2,4-TRIMETHYLBENZENE WITH PERACETIC ACID
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The oxidation of 1,2,4-trimethylbenzene with peracetic acid leads to the formation of trimethylphenols and hydroquinones, which undergo transformations to the corresponding benzoquinones and products from oxidative cleavage of the ring.The controlling stage of the process is the electrophilic hydroxylation of 1,2,4-trimethylbenzene.
- Kharchuk, V. G.,Kolenko, I. P.,Petrov, L. A.,Gus'kova, L. M.
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p. 2071 - 2078
(2007/10/02)
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