15448-58-5Relevant articles and documents
Reactions of peroxynitrite with N,N-dimethyl-p-toluidine and 1,4-naphthoquinone. Evidence for heterolytic cleavage of a nitrogen-oxygen bond in peroxynitrous acid
Nonoyama, Nobuaki,Hisatome, Kaori,Shoda, Chizuru,Suzuki, Hitomi
, p. 6939 - 6940 (1999)
Peroxynitrite (ONOO-) has been found to react with the title amine 1 and quinone 5 to form N-nitrosoamine 2 and 2,3-epoxide 6, respectively, in accord with the in situ generation of the nitrosonium and hydroperoxide ions as the respective reactive species.
Bioactivity profiles of cytoprotective short-chain quinones
Chear, Sueanne,Feng, Zikai,Gueven, Nuri,Hemasa, Ayman L.,Nadikudi, Monila,Smith, Jason A.,Woolley, Krystel L.
supporting information, (2021/05/31)
Short-chain quinones (SCQs) have been investigated as potential therapeutic candidates against mitochondrial dysfunction, which was largely thought to be associated with the reversible redox characteristics of their active quinone core. We recently reported a library of SCQs, some of which showed potent cytoprotective activity against the mitochondrial complex I inhibitor rotenone in the human hepatocarcinoma cell line HepG2. To better characterize the cytoprotection of SCQs at a molecular level, a bioactivity profile for 103 SCQs with different compound chemistries was generated that included metabolism related markers, redox activity, expression of cytoprotective proteins and oxidative damage. Of all the tested endpoints, a positive correlation with cytoprotection by SCQs in the presence of rotenone was only observed for the NAD(P)H:quinone oxidoreductase 1 (NQO1)-dependent reduction of SCQs, which also correlated with an acute rescue of ATP levels. The results of this study suggest an unexpected mode of action for SCQs that appears to involve a modification of NQO1-dependent signaling rather than a protective effect by the reduced quinone itself. This finding presents a new selection strategy to identify and develop the most promising compounds towards their clinical use.
Pyrenediones as versatile photocatalysts for oxygenation reactions with: In situ generation of hydrogen peroxide under visible light
Zhang, Yuannian,Yang, Xin,Tang, Haidi,Liang, Dong,Wu, Jie,Huang, Dejian
supporting information, p. 22 - 27 (2020/01/13)
Pyrenediones (PYDs) are efficient photocatalysts for three oxygenation reactions: Epoxidation of electron deficient olefins, oxidative hydroxylation of organoborons, and oxidation of sulfides via in situ generation of H2O2 under visible light irradiation, using oxygen as a terminal oxidant and IPA as a solvent and a hydrogen donor.
Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase
Calil, Felipe A.,David, Juliana S.,Chiappetta, Estela R.C.,Fumagalli, Fernando,Mello, Rodrigo B.,Leite, Franco H.A.,Castilho, Marcelo S.,Emery, Flavio S.,Nonato, M.Cristina
, p. 357 - 366 (2019/02/19)
Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 ± 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization.
Method for preparing epoxide by one-pot olefin aerobic epoxidation
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Paragraph 0060-0061, (2020/01/03)
The invention relates to a method for preparing an epoxide by one-pot olefin aerobic epoxidation, and belongs to the technical field of organic synthesis. An olefin, an alkyl aromatic compound and analkali are added into a solvent, or an olefin, an alkyl aromatic compound and an alkali are directly mixed; the temperature is raised to 70-160 DEG C in an air or oxygen atmosphere; reacting is carried out for 1-48 hours; and the olefin is directly oxidized into the corresponding epoxide in the presence of the alkyl aromatic compound, the alkali and air (or oxygen), wherein the yield is up to 99%.In the reaction process, the generated alkyl peroxide is generated in situ and consumed in situ, so that the concentration of the alkyl peroxide is kept at a lower level; and generated alkyl peroxy free radicals can also react with the olefin to further generate the peroxide, and efficiency is improved. The method has the advantages of simple operation, mild conditions, low raw material cost andno need of special complex equipment, and has a good industrial application prospect.
Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents
Acu?a, Julio,Piermattey, Jhoan,Caro, Daneiva,Bannwitz, Sven,Barrios, Luis,López, Jairo,Ocampo, Yanet,Vivas-Reyes, Ricardo,Aristizábal, Fabio,Gaitán, Ricardo,Müller, Klaus,Franco, Luis
, (2018/02/06)
Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.
Significant effect of 5,10,15,20-meso-tetraarylporphyrinatoiron(III) chloride/triflate and acidic/neutral/basic imidazolium ionic liquids in catalytic oxidation of phenols
Ahmad, Sohail,Gautam, Renu,Singhal, Anchal,Chauhan
, p. 292 - 303 (2018/04/10)
The influence of acidic, neutral and basic ionic liquids and their binary mixture with dichloromethane on the reactivity of iron(III)porphyrins was investigated during oxidation of phenols with hydrogen peroxide catalysed by 5,10,15,20-tetraarylporphyrinatoiron(III) chloride and 5,10,15,20-tetraarylporphyrinatoiron(III) triflate. The generation of different intermediates of iron(III) porphyrin in different ILs was studied through viscosity, density, UV–Vis and 1H NMR spectroscopy. The heterolytic cleavage efficiency of (TAP)FeIII-OOH and formation of quinone using iron(III)porphyrin (TAP)FeIIICl with Cl atom as an axial ligand, is influenced by the structure of imidazolium moiety and the counteranion following the order [(CH2)4SO3HMIm]CF3COO > [Hmim]CF3COO > [bmim]TFA ?? negligible amount in [bmim]CF3SO3, [Hmim]CF3SO3, [bmim]BF4, [bmim]PF6 and [bmim]Cl. On the other hand, the heterolytic cleavage efficiency of (TAP)FeIII-OOH with iron(III)porphyrin (TAP)FeIIICF3SO3 with triflate as an axial ligand, was found in the following order [(CH2)4SO3HMIm]CF3SO3 > [Hmim]CF3SO3 > [(CH2)4SO3HMIm]CF3COO > [Hmim]CF3COO > [bmim] CF3COO > [bmim]PF6 ≈ [bmim]BF4 ≈ [bmim]CF3SO3, while epoxidation and polymerization were mainly observed in basic and neutral ILs. The reactive intermediates formed by the reaction of monooxygen donors with (TAP)FeIIICl varied with ILs, as (TAP)+?FeIV = O intermediate was dominated in acidic ILs, while (TAP)FeIV = O was formed in neutral ILs and (TAP)FeIII-OO– was formed in basic ILs.
Concentrated Aqueous Sodium Tosylate as Green Medium for Alkene Oxidation and Nucleophilic Substitution Reactions
Sela, Tal,Lin, Xiaoxi,Vigalok, Arkadi
, p. 11609 - 11612 (2017/11/10)
A hydrotropic solution of highly concentrated sodium tosylate (NaOTs) can be used as a recyclable medium for the environmentally benign oxidation of conjugated alkenes with H2O2. Both uncatalyzed and metal-catalyzed reactions provided the corresponding oxidation products in higher yields than in pure water or many common organic solvents.
Tetrabutylammonium Iodide Catalyzed Epoxidation of Naphthoquinone Derivatives with tert -Butyl Hydroperoxide as an Oxidant
Ai, Bai-Ru,Chen, Xu-Ling,Dong, Yu,Tang, Lei,Wang, Ji-Yu
, p. 4017 - 4024 (2017/08/29)
An efficient and environmentally benign procedure has been developed for the epoxidation of naphthoquinone derivatives by using tetrabutylammonium iodide as a catalyst and tert -butyl hydroperoxide as an oxidant in the presence of silicon dioxide. This protocol, which provides a facile base-free methodology for the synthesis of some new naphthoquinone-based epoxides, features mild reaction conditions, high yields, remarkably short reaction time, and broad substrate scope.
Ru-Catalyzed Asymmetric Hydrogenative/Transfer Hydrogenative Desymmetrization of Meso-Epoxy Diketones
Hong, Yuping,Chen, Jianzhong,Zhang, Zhenfeng,Liu, Yangang,Zhang, Wanbin
supporting information, p. 2640 - 2643 (2016/06/15)
Via a strategy of asymmetric reductive desymmetrization, chiral cis-epoxy naphthoquinols with multiple contiguous stereocenters and functional groups were synthesized with excellent enantioselectivities (96-99% ee) and diastereoselectivities (8/1-15/1). A combined asymmetric hydrogenation/transfer hydrogenation mechanism was proposed based on experimental results.
