5018-87-1Relevant academic research and scientific papers
Mechanochemical Friedel-crafts acylations
Dud, Mateja,Bri?, Anamarija,Ju?inski, Iva,Gracin, Davor,Margeti?, Davor
supporting information, p. 1313 - 1320 (2019/07/08)
Friedel-Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.
Discovery of Novel Naphthylphenylketone and Naphthylphenylamine Derivatives as Cell Division Cycle 25B (CDC25B) Phosphatase Inhibitors: Design, Synthesis, Inhibition Mechanism, and in Vitro Efficacy against Melanoma Cell Lines
Cerchia, Carmen,Nasso, Rosarita,Mori, Matteo,Villa, Stefania,Gelain, Arianna,Capasso, Alessandra,Aliotta, Federica,Simonetti, Martina,Rullo, Rosario,Masullo, Mariorosario,De Vendittis, Emmanuele,Ruocco, Maria Rosaria,Lavecchia, Antonio
, p. 7089 - 7110 (2019/08/20)
CDC25 phosphatases play a critical role in the regulation of the cell cycle and thus represent attractive cancer therapeutic targets. We previously discovered the 4-(2-carboxybenzoyl)phthalic acid (NSC28620) as a new CDC25 inhibitor endowed with promising anticancer activity in breast, prostate, and leukemia cells. Herein, we report a structure-based optimization of NSC28620, leading to the identification of a series of novel naphthylphenylketone and naphthylphenylamine derivatives as CDC25B inhibitors. Compounds 7j, 7i, 6e, 7f, and 3 showed higher inhibitory activity than the initial lead, with Ki values in the low micromolar range. Kinetic analysis, intrinsic fluorescence studies, and induced fit docking simulations provided a mechanistic understanding of the activity of these derivatives. All compounds were tested in the highly aggressive human melanoma cell lines A2058 and A375. Compound 4a potently inhibited cell proliferation and colony formation, causing an increase of the G2/M phase and a reduction of the G0/G1 phase of the cell cycle in both cell lines.
Synthesis, Structure, and Properties of Tetrabenzo[7]circulene
Gu, Xiao,Li, Huiyan,Shan, Bowen,Liu, Zhifeng,Miao, Qian
supporting information, p. 2246 - 2249 (2017/05/12)
Tetrabenzo[7]circulene, a new member of aromatic saddles, was conveniently synthesized from 2-(1-naphthoyl)benzoic acid with the seven-membered ring constructed at an early stage of the synthesis. This method, upon minor modification, was also useful for synthesis of thiophene-annulated [7]circulenes. The structures of tetrabenzo[7]circulene and [7]circulene were compared in terms of symmetry, flexibility, and curvature on the basis of DFT calculations and X-ray crystallography. It was also found that tetrabenzo[7]circulene functioned as a p-type semiconductor in thin-film transistors and cocrystallized with C60
Synthesis of uniformly 13C-labeled polycyclic aromatic hydrocarbons
Zhang, Zhenfa,Sangaiah, Ramiah,Gold, Avram,Ball, Louise M.
, p. 5431 - 5435 (2011/09/14)
Convergent synthetic pathways were devised for efficient synthesis of a series of uniformly 13C labeled polycyclic aromatic hydrocarbons de novo from U-13C-benzene and other simple commercially-available 13C-starting compounds. All target products were obtained in excellent yields, including the alternant PAH U-13C-naphthalene, U-13C-phenanthrene, U-13C-anthracene, U- 13C-benz[a]anthracene, U-13C-pyrene and the nonalternant PAH U-13C-fluoranthene.
Direct synthesis of γ-substituted phthalides by cyclization of benzyl radicals generated from o-(arylmethyl)benzoic acids
Mahmoodi,Salehpour
, p. 1760 - 1763 (2007/10/03)
Direct oxidation of o-(arylmethyl)benzoic acids with sodium peroxysulfate-copper(II) chloride in water yields γ-substituted phthalides. The reaction is highly regioselective, and the corresponding γ-butyro-lactones are the only products formed through intermediate stable arylmethyl radicals.
Direct Synthesis of γ-Substituted Phthalides Via ortho-Aryl Benzoic Acid Mediated Benzyl Radical Cyclization
Mahmoodi,Salehpour
, p. 875 - 878 (2007/10/03)
Direct synthesis of γ-substituted phthalids from related ortho-aryl benzoic acids with 48-85% yield are covered. The direct oxidation in the presence of peroxydisulphate-copper (II) chloride in aqueous medium was applied. The reaction is highly regioselective and leads exclusively to γ-butyrolactone, through very stable benzylic radical intermediate.
Acid-Catalyzed Cyclization of o-Aroylbenzoic and Diarylcarboxylic Acids upon Heating in Vacuum
Nefedov
, p. 375 - 377 (2007/10/03)
The cyclization of 1,1′-dinaphthyl-8,8′-dicarboxylic acid, diphenic anhydride, o-benzoylbenzoic acid, and 1-naphthoyl-o-benzoic acid into, respectively, anthanthrone, fluorenone-4-carboxylic acid, anthraquinone, and 1,2-benzanthraquinone occurs upon heating to 150-200°C in vacuum in the presence of catalytic amounts (1-3%) of H2SO4 or P2O5.
Improved Synthesis and Crystal Structure of 7H-Dibenzanthracen-7-one
Fujisawa, Shoi,Oonishi, Isao,Aoki, Junji,Ohashi, Yuji,Sasada, Yoshio
, p. 3356 - 3359 (2007/10/02)
An improved synthetic method gives pure 7H-dibenzanthracen-7-one, C21H12O, in a higher yield than those reported so far.The crystal structure has been determined by X-ray analysis.The space group is Pn21a, with unit cell dimensions of a=23.325(5), b=14.149(3), c=3.986(1) A, and Z=4.The structure was solved by the direct method and refined by the block-diagonal least-squares method to an R value of 0.044.The molecule is greatly distorted from the planar conformation because of an intramolecular steric repulsion between the hydrogen atoms.
