84-11-7Relevant articles and documents
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Patrick et al.
, p. 3413 (1976)
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Synthesis, characterization, DNA binding and cleaving properties of photochemically activated phenanthrene dihydrodioxin
Tikhomirova, Anastasiia A.,Tcyrulnikov, Nikolai A.,Wilson, R. Marshall
, (2019)
Dihydrodioxin compounds are formed upon visible light irradiation of a mixture of an ortho-quinone and a substituted alkene. The reverse photochemical reaction can result in the release of a highly reactive ortho-quinone that can induce oxidative DNA damage. A novel DNA binding and cleaving phenanthrene dihydrodioxin compound (1)was synthesized. The photochemical release of 9,10-phenanthrenequinone was studied under different light irradiation wavelengths. Interaction of 1 with DNA caused an increase in the viscosity of DNA as well as hypochromic effect and a bathochromic shift in the absorption of 1. These results indicated the intercalative mode of binding of 1 to DNA. Binding affinities of 1 to several DNA sequences were evaluated, and slightly preferential binding to AT-rich DNA oligomers was observed. Intercalation of 1 between CT-DNA base pairs induced a partial transition from B-form to Z-form of DNA. Significant stabilization of the DNA duplex was revealed by DNA optical melting experiments with 33 % GC 12-mer (?Tm = 9 oC). ΦX174 photocleavage assay showed that 1 is capable of > 90 % single-strand DNA cleavage and ~ 5 % of double-strand DNA breakage. Therefore, 1 further demonstrates the potential of masked orhto-quinones as efficient photoactivated DNA cleaving agents.
Tautomerism of Representative Aromatic α-Hydroxy Carbaldehyde Anils as Studied by Spectroscopic Methods and AM1 Calculations. Synthesis of 10-Hydroxyphenanthrene-9-carbaldehyde
Alarcon, Sergio H.,Olivieri, Alejandro C.,Labadie, Guillermo R.,Cravero, Raquel M.,Gonzalez-Sierra, Manuel
, p. 4619 - 4626 (1995)
The synthesis of 10-hydroxyphenanthrene-9-carbaldehyde and its anil are described.The structure of the latter compound has been thoroughly studied by 1H and 13C NMR, UV-visible absorption, fluorescence and IR spectroscopies.All the experimental results support the existence of this anil mainly in the keto-enamine tautomeric form.A comparison is presented with previously studied anils derived from salicylaldehyde and 2-hydroxynaphthalene-1-carbaldehyde.Semiempirical calculations (AM1) concerning the relative stability of tautomers as well as the optimized molecular geometries are in good agreement with the experimental findings.
Synthetic models for catechol 1,2-dioxygenases. Interception of a metal catecholate - dioxygen adduct
Barbaro, Pierluigi,Bianchini, Claudio,Mealli, Carlo,Meli, Andrea
, p. 3181 - 3183 (1991)
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Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils
Zhu, Jia-Liang,Tsai, Yi-Ting
, p. 813 - 828 (2020/12/22)
The conversion of 1,3-diaryl-2-diazo-1,3-diketones to 1,2-daryl-1,2-diketones (benzils) is reported based on a rhodium(II)-catalyzed aerobic decomposition process. The reaction occurs at ambient temperatures and can be catalyzed by a few dirhodium carboxylates (5 mol %) under a balloon pressure of oxygen. Moreover, an oxygen atom from the O2 reagent is shown to be incorporated into the product, and this is accompanied by the extrusion of a carbonyl unit from the starting materials. Mechanistically, it is proposed that the decomposition may proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone were synthesized from the corresponding diazo substrates in varying yields. On the other hand, the method did not allow the generation of benzocyclobutene-1,2-dione from 2-diazo-1,3-indandione because of the difficulty of inducing the initial rearrangement.
Unexpected radical mechanism in a [4+1] cycloaddition reaction
Bors, István,Purgel, Mihály,Fehér, Péter Pál,Varga, Tamás,Speier, Gábor,Korecz, László,Kaizer, József
supporting information, p. 8440 - 8444 (2021/05/25)
9,10-Phenanthrenequinone monoimines (2,7-R-PQI, R = tBu, H, Br, NO2, 1a-d) undergo a [4+1] cycloaddition reaction with triphenylphosphine to give 2,3-dihydro-2,2,2-triphenylphenanthro[9,10-d]-1,3,2λ5-oxazaphospholes (3a-d). During the reaction, highly colored radicals are formed as intermediates, which were characterized by EPR and UV-vis spectroscopy. The formation rate and the rate of decay of these radicals were determined kinetically. These radicals exhibit high persistency and under inert conditions can be handled conveniently. Based on detailed kinetic and spectroscopic studies and DFT calculations, a plausible mechanism has been proposed. This journal is
Suzuki cross coupling followed by cross dehydrogenative coupling: An efficient one pot synthesis of Phenanthrenequinones and analogues
Ahmed, Atiur,Ray, Jayanta K.,Sarkar, Pompy
supporting information, (2020/03/05)
An efficient one pot protocol has been developed towards the synthesis of substituted phenanthrenequinone and analogous derivatives via Suzuki cross coupling followed by copper catalyzed cross dehydrogenative coupling.