![4-methoxydibenzo[b,d]furan](/Databaselist/images/loading.webp)
19261-06-4Relevant academic research and scientific papers
DNA-dependent protein kinase (DNA-PK) inhibitors. synthesis and biological activity of quinolin-4-one and pyridopyrimidin-4-one surrogates for the chromen-4-one chemotype
Cano, Céline,Barbeau, Olivier R.,Bailey, Christine,Cockcroft, Xiao-Ling,Curtin, Nicola J.,Duggan, Heather,Frigerio, Mark,Golding, Bernard T.,Hardcastle, Ian R.,Hummersone, Marc G.,Knights, Charlotte,Menear, Keith A.,Newell, David R.,Richardson, Caroline J.,Smith, Graeme C. M.,Spittle, Ben,Griffin, Roger J.
, p. 8498 - 8507 (2010)
Following the discovery of dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H- chromen-4-one (NU7441) (Leahy, J. J. J.; Golding, B. T.; Griffin, R. J.; Hardcastle, I. R.; Richardson, C.; Rigoreau, L.; Smith, G. C. M. Bioorg. Med. Chem. Lett. 2004, 14, 6083-6087) as a potent inhibitor (IC50 = 30 nM) of DNA-dependent protein kinase (DNA-PK), we have investigated analogues in which the chromen-4-one core template has been replaced by aza-heterocyclic systems: 9-substituted 2-morpholin-4-ylpyrido[1,2-a]pyrimidin-4-ones and 8-substituted 2-morpholin-4-yl-1H-quinolin-4-ones. The 8- and 9-substituents were either dibenzothiophen-4-yl or dibenzofuran-4-yl, which were each further substituted at the 1-position with water-solubilizing groups [NHCO(CH 2)nNR1R2, where n = 1 or 2 and the moiety R1R2N was derived from a library of primary and secondary amines (e.g., morpholine)]. The inhibitors were synthesized by employing a multiple-parallel approach in which the two heterocyclic components were assembled by Suzuki-Miyaura cross-coupling. Potent DNA-PK inhibitory activity was generally observed across the compound series, with structure activity studies indicating that optimal potency resided in pyridopyrimidin-4- ones bearing a substituted dibenzothiophen-4-yl group. Several of the newly synthesized compounds (e.g., 2-morpholin-4-yl-N-[4-(2-morpholin-4-yl-4-oxo-4H- pyrido[1,2-a]pyrimidin-9-yl)dibenzothiophen-1-yl]acetamide) combined high potency against the target enzyme (DNA-PK IC50 = 8 nM) with promising activity as potentiators of ionizing radiation-induced cytotoxicity in vitro.
Design, synthesis, and properties of conformationally fixed semiquinone monoradical species
Shultz, David A.,Sloop, Joseph C.,Washington, Gary
, p. 9104 - 9113 (2006)
(Graph Presented) The design of novel, functionalized semiquinone (SQ) ligands which combine structural rigidity and electron-withdrawing, electron-donating, and electroneutral substituents enables investigation of multiple structure-property relationships and building blocks for new materials, including components of sensors, switches, and molecular spintronics. Along these lines, we report the synthesis of several new SQ ligands containing fused heterocyclic ring systems. Using both electron paramagnetic resonance spectroscopy and quantum chemical calculations, we show how spin density is affected by the fused ring system substituents.
Blacklight-Induced Hydroxylation of Arylboronic Acids Leading to Hydroxyarenes Using Molecular Oxygen and Tetrabutylammonium Borohydride
Kawamoto, Takuji,Ryu, Ilhyong
, (2021/09/06)
A new simple protocol for the conversion of arylboronic acids to hydroxyarenes was achieved using molecular oxygen in the presence of tetrabutylammonium borohydride under blacklight irradiation (360 nm). A radical chain mechanism in which a superoxide ion (O2?.) plays a key role is proposed.
Cellulose as recyclable organocatalyst for ipso-hydroxylation of arylboronic acids
Laskar, Khairujjaman,Paul, Subham,Bora, Utpal
, (2019/08/26)
Cellulose catalyzed oxidative hydroxylation of aryl and hetero-arylboronic acids to the corresponding phenols under metal and base free strategy has been demonstrated. The sustainable ipso-hydroxylation takes place using hydrogen peroxide as an oxidant in water under mild condition in shorter period of time. Interestingly, easy recovery and reusability of heterogeneous catalyst without significant loss in catalytic yield makes the protocol environmentally benign.
A practical method for preparation of phenols from arylboronic acids catalyzed by iodopovidone in aqueous medium
Dong, Bin,Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Ren, Yaoyao,Zeng, Bu-Bing,Zhou, Bin
, (2019/09/06)
A novel and efficient strategy for the ipso-hydroxylation of arylboronic acids to phenols has been developed using inexpensive, readily available, air-stable water-soluble povidone iodine as catalyst and aqueous hydrogen peroxide as oxidizing agent. The reactions were performed at room temperature under metal-, ligand- and base-free condition in a short reaction time. The corresponding substituted phenols were obtained in moderate to good yields by oxidative hydroxylation of arylboronic acids in aqueous medium.
Trichloroacetonitrile as an efficient activating agent for the: Ipso -hydroxylation of arylboronic acids to phenolic compounds
Fang, Yuanding,Zhao, Rong,Yao, Yuan,Liu, Yang,Chang, Denghu,Yao, Ming,Shi, Lei
, p. 7558 - 7563 (2019/08/20)
A metal-free and base-free Cl3CCN mediated method was developed for the ipso-hydroxylation of aryl boronic acids to their corresponding phenols, which was promoted by a key unstable Lewis adduct intermediate. This transformation has broad functional group tolerance, and late-stage functionalization was successful as well. After simple investigation, two pathways (radical/ionic mechanism) were suggested, and the beneficial action of blue light needs to be further studied.
Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide
Weng, Wei-Zhi,Liang, Hao,Zhang, Bo
supporting information, p. 4979 - 4983 (2018/08/24)
A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.
Rapid Access to Bi- and Tri-Functionalized Dibenzofurans and their Application in Selective Suzuki–Miyaura Cross Coupling Reactions
Wern, Caroline,Ehrenreich, Christian,Joosten, Dominik,Stein, Thorsten vom,Buchholz, Herwig,K?nig, Burkhard
, p. 5644 - 5656 (2018/10/09)
Syntheses of 1,2-, 1,3-, 1,4-, 1,8-, 2,4-, 3,4-, 4,8-, 1,2,4-, 1,2,8- and 1,3,4-functionalized dibenzofurans in few steps with good to excellent yields starting from dibenzofuran-1-ol or -4-ol are presented. These rapidly accessible bi- or tri-functionalized building blocks are of great interest for the synthesis of bioactive substances or functional material development. Furthermore, for intermediates containing both a bromine and a triflate moiety, a selective mono-substitution by means of Suzuki–Miyaura reaction (SMR) is described.
A catalytic oxidation fragrant boron class compound preparing phenol method (by machine translation)
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Paragraph 0073; 0101; 0102, (2017/08/08)
The invention discloses a method for catalytic oxidation of phenolic compounds fragrant boron class compound synthesis method, the flux in the solvent in the aqueous solution, under the action of alkali, adding hydrazine hydrate or acid hydrazides catalyst, catalytic oxidation fragrant boron class compound directly for the preparation of phenolic compound. The invention of the method of preparation of the phenol compound, the catalyst is a cheap hydrazine hydrate or hydrazine compound, the oxidizing agent is atmospheric pressure of air or oxygen, the reaction does not need good and activeness metal catalyst, is extensive and stable substrate, substrate-sensitive functional group compatibility good and wide range of application. In the optimized under the reaction conditions, the yield of the target product separation up to 99%. (by machine translation)
Biogenic synthesis of Fe2O3@SiO2 nanoparticles for ipso-hydroxylation of boronic acid in water
Saikia, Indranirekha,Hazarika, Moushumi,Hussian, Najrul,Das, Manash R.,Tamuly, Chandan
, p. 4255 - 4259 (2017/10/11)
Here, biogenic synthesis of Fe2O3@SiO2 nanoparticles using fruit extract of Zanthoxylum rhetsa is reported. The SiO2 nanoparticles was synthesized using paddy straw which is a byproduct obtained in cultivation of rice. The composite was characterised by spectroscopic method like XRD, SEM, TEM and EDX analysis. The ipso-hydroxylation reactions were carried out with excellent yield within a moderate time period with mild reaction condition in all cases. Therefore, this approach may be considered as simple, easy, cheap and greener, environment friendly protocol for ipso-hydroxylation of arylboronic acids at 50 °C temperature.
