- C-to N-Center Remote Heteroaryl Migration via Electrochemical Initiation of N Radical by Organic Catalyst
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Herein an exogenous oxidant- A nd metal-free electrochemical heteroaryl migration triggered by N radicals to construct new N-C bonds was developed. This methodology features a high atom economy and utilization rate of energy, and it is insensitive to water and air. Moreover, a user-friendly undivided cell was employed. The use of an organic catalyst makes it more efficient, green, and practical.
- Liu, Chengkou,Jiang, Qiang,Lin, Yang,Fang, Zheng,Guo, Kai
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- Sulphonamide chalcones: Conformationally diverse yet optically similar
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In this paper, we present the synthesis of three chalcone analogues and their spectroscopic, structural and optical characterization. The influence of the different substituents on the crystalline structure and on their optical properties was evaluated. T
- Custodio, Jean M.F.,Gotardo, Fernando,Vaz, Wesley F.,D'Oliveira, Giulio D.C.,Cocca, Leandro H.Z.,Fonseca, Ruben D.,Perez, Caridad Noda,de Boni, Leonardo,Napolitano, Hamilton B.
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- On the: In silico and in vitro anticancer activity of sulfonamide chalcones: Potential JNKK3 inhibitors
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Science is constantly looking for new strategies to combat tumor progression and improve patient care due to increasing cancer incidence and high mortality. Although many chalcone analogues have been synthesized and studied because of their activity against tumor cell growth, the use of hybrid compounds containing both sulfonamides and chalcone moieties for this purpose is still scarce. Hereby, this work proposes a series of sulfonamide chalcones presenting biological potential against this disease. After being experimentally tested, these compounds showed cytotoxicity against tumor cell lines SF-295 and PC-3, which motivated us to investigate the possible structural bases for this action. Topological analyses were carried out through Hirshfeld analysis to assign intermolecular interaction sites important for protein-ligand analysis. To identify potential targets, the synthesized compounds were submitted to a structure-based pharmacophoric screening, which suggest strong potential activity as mitogen-Activated protein kinase 10 (JKN3) inhibitors. Considering these results, these compounds were docked within the JKN3 active site. Our hypothesis that these compounds achieve their biological potential by inhibiting the JKN3 protein is reinforced when their energies of ligand-protein interaction were compared to co-crystallized ligands: They showed similar or even lower binding energies. Finally, the energy of the different conformations (solid phase, aqueous phase and within the protein active site) of these sulfonamide chalcones was investigated using theoretical calculations. Our findings enable further studies on more sulfonamide chalcone analogues toward the development of new anticancer drugs.
- Custodio, Jean M. F.,De Moraes, Manoel O.,Moura, Andrea F.,Napolitano, Hamilton B.,Perez, Caridad N.
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- Synthesis, characterization and evaluation of in vitro antitumor activities of novel chalcone-quinolinone hybrid compounds
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Chalcone-quinolinone hybrid compounds, as well as the synthesis of such compounds, have few reports in the literature. Such compounds may be quite useful in therapeutics, since various biological activities are reported for both chalcones and quinolinones. In the present work, several novel chalcone-quinolinone compounds have been synthesized. The reaction conditions developed allowed to obtain the compounds in a single step of synthesis from the chalcones. The products precipitated pure and were isolated by filtration. The yields of such reactions, from 45 to 94percent, were promising. The product structures were confirmed by nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS) techniques. Their antitumor activities were evaluated in HCT-116 (colon) cell lines by the 3-(4,5-dimethyl-2-thiazole)-2,5-diphenyl-2-H-tetrazolium bromide (MTT) test. The half maximal inhibitory concentration (IC50) values obtained for the most active chalcones were between 2.9 and 7.5 and for active quinolinone was 19.3 mg L-1. The antitumor activities results suggest that the class of compounds studied has potential for use in cancer research.
- D’Oliveira, Giulio D. C.,Moura, Andrea F.,De Moraes, Manoel O.,Perez, Caridad N.,Li?o, Luciano M.
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- Second-order nonlinear optical properties of two chalcone derivatives: insights from sum-over-states
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In this study, a combined experimental and theoretical study of the nonlinear optical properties (NLO) of two chalcone derivatives, (E)-3-(2-methoxyphenyl)-1-(2-(phenylsulfonylamine)phenyl)prop-2-en-1-one (MPSP) and (E)-3-(3-nitrophenyl)-1-(2-(phenylsulfo
- Custodio, Jean M. F.,D’Oliveira, Giulio D. C.,Gotardo, Fernando,Cocca, Leandro H. Z.,de Boni, Leonardo,Perez, Caridad N.,Napolitano, Hamilton B.,Osorio, Francisco A. P.,Valverde, Clodoaldo
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- Iron-Catalyzed Electrophilic Amination of Sodium Sulfinates with Anthranils
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A practical method for the synthesis of N-(2-carbonylaryl) benzenesulfonamides via an iron-catalyzed electrophilic amination of sodium sulfinates with anthranils is described. This redox-neutral transformation has high atom efficiency and is achieved under simple and mild reaction conditions. A wide range of anthranils and sodium sulfinates were compatible in this transformation. Moreover, the synthetic potential of this methodology was further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
- Liang, Baihui,Huang, Junjie,Zhu, Weidong,Li, Yawen,Jiang, Lanping,Gao, Yang,Xie, Feng,Li, Yibiao,Chen, Xiuwen,Zhu, Zhongzhi
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p. 1466 - 1473
(2021/02/09)
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- Synthesis method of o-acylaniline sulfonamide compound
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The invention discloses a synthesis method of a o-acylaniline sulfonamide compound. The preparation method is characterized by comprising the following steps: mixing a benzisoxazole compound as shownin a chemical formula I, a sodium sulfinate compound as shown in a chemical formula II, a metal catalyst and a solvent, and reacting to obtain the o-acylaniline sulfonamide compound as shown in a chemical formula III, in the formula, R1 is a monosubstituted or polysubstituted group on a benzene ring. The synthesis method can be used for efficiently synthesizing the o-acylaniline sulfonamide compound, has the advantages of simple synthesis steps, safety in operation, good compatibility of the synthesis method to functional groups and high atom economy, and is easy for industrial synthesis.
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Paragraph 0131-0138
(2020/10/30)
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- Visible-light-promoted N-centered radical generation for remote heteroaryl migration
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Herein, an efficient visible-light-mediated N-H heteroarylationviaremote heteroarylipso-migration has been accomplished. Moderate to good yields were obtained with good functional group tolerance. Moreover, a simple and readily available organic photoredox catalyst was employed, avoiding the use of complex and costly noble metal compounds.
- Cai, Chen,Fang, Zheng,Guo, Kai,Jiang, Qiang,Liu, Chengkou,Yuan, Chengcheng
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supporting information
p. 7663 - 7670
(2020/10/14)
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- Manganese-Catalyzed ortho-C-H Amidation of Weakly Coordinating Aromatic Ketones
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An efficient manganese-catalyzed ortho-C-H amidation of weakly coordinating aromatic ketones using the readily available sulfonyl azide as the amination reagent is developed. The key step is the ketone directed aromatic metalation using the in situ generated reactive Mn intermediate, MnMe(CO)5. This method offers excellent chemical yields, high regioselectivities, and good functional group tolerance.
- Kong, Xianqiang,Xu, Bo
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supporting information
p. 4495 - 4498
(2018/08/07)
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- Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones
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C-H activation: The ruthenium-catalyzed direct sp2 C-H amidation of arenes by using sulfonyl azides as the amino source is presented (see scheme). A wide range of substrates were readily amidated including arenes bearing weakly coordinating groups. Synthetic utility of the thus obtained products was demonstrated in the preparation of biologically active heterocycles. Copyright
- Kim, Jiyu,Kim, Jinwoo,Chang, Sukbok
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supporting information
p. 7328 - 7333
(2013/06/27)
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- One-pot synthesis of 1-phenylsulfonyl-2-aroylindoles
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Interaction of phenylsulfonyl-2-aminobenzaldehyde with 2-bromo-1- phenylethanones in the presence of K2CO3 followed by acid-catalyzed dehydration led to the formation of 1-phenylsulfonyl-2-aroylindoles.Copyright Taylor & Francis Group, LLC.
- Dhayalan, Vasudevan,Panchapakesan, Ganapathy,Mohanakrishnan, Arasambattu K.
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experimental part
p. 402 - 411
(2011/11/13)
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- Direct conversion of azides to carbamates and sulfonamides using Fe/NH4Cl: Effect of sonication
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A simple, direct and effective conversion of azides to carbamates and sulfonamides is achieved using Fe/NH4Cl in methanol. The influence of sonication and direct application in solution phase combinatorial chemistry are also studied by developing a 6x4 matrix library. (C) 2000 Elsevier Science Ltd.
- Chandrasekhar,Narsihmulu
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p. 7969 - 7972
(2007/10/03)
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- SYNTHESIS OF 1-(PHENYLSULFONYL)INDOL-3-YL TRIFLUOROMETHANESULFONATE
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The synthesis of the potentially useful intermediate 1-(phenylsulfonyl)indol-3-yl trifluoromethanesulfonate (triflate) (1), via several approaches to the corresponding indoxyl 6, is decsribed.Of these, the direct oxidation of 1-(phenylsulfonyl)indole (2)
- Conway, Samuel C.,Gribble, Gordon W.
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p. 627 - 633
(2007/10/02)
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