- Visible-Light-Induced Radical Carbo-Cyclization/ gem-Diborylation through Triplet Energy Transfer between a Gold Catalyst and Aryl Iodides
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Geminal diboronates have attracted significant attention because of their unique structures and reactivity. However, benzofuran-, indole-, and benzothiophene-based benzylic gem-diboronates, building blocks for biologically relevant compounds, are unknown. A promising protocol using visible light and aryl iodides for constructing valuable building blocks, including benzofuran-, indole-, and benzothiophene-based benzylic gem-diboronates, via radical carbo-cyclization/gem-diborylation of alkynes with a high functional group tolerance is presented. The utility of these gem-diboronates has been demonstrated by a 10 g scale conversion, by versatile transformations, by including the synthesis of approved drug scaffolds and two approved drugs, and even by polymer synthesis. The mechanistic investigation indicates that the merging of the dinuclear gold catalyst (photoexcitation by 315-400 nm UVA light) with Na2CO3 is directly responsible for photosensitization of aryl iodides (photoexcitation by 254 nm UV light) with blue LED light (410-490 nm, λmax = 465 nm) through an energy transfer (EnT) process, followed by homolytic cleavage of the C-I bond in the aryl iodide substrates.
- Hashmi, A. Stephen K.,Rominger, Frank,Si, Xiaojia,Zhang, Lumin
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p. 10485 - 10493
(2020/07/03)
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- A chiral enantioseparation generic strategy for anti-Alzheimer and antifungal drugs by short end injection capillary electrophoresis using an experimental design approach
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The present study describes a generic strategy using capillary electrophoretic (CE) method for chiral enantioseparation of anti-Alzheimer drugs, namely, donepezil (DON), rivastigmine (RIV), and antifungal drugs, namely, ketoconazole (KET), Itraconazole (ITR), fluconazole (FLU), and sertaconazole (SRT) in which these drugs have different basic and acidic properties. Several modified cyclodextrins (CDs) were applied for enantioseparation of racemates such as highly sulfated α, γ CDs, hydroxyl propyl-β-CD, and Sulfobutyl ether-β-CD. The starting screening conditions consist of 50-mM phosphate-triethanolamine buffer at pH?2.5, an applied voltage of 15?kV, and a temperature of 25°C. The CE strategy implemented in the separation starts by screening prior to the optimization stage in which an experimental design is applied. The design of experiment (DOE) was based on a full factorial design of the crucial two factors (pH and %CD) at three levels, to make a total of nine (32) experiments with high, intermediate, and low values for both factors. Evaluation of the proposed strategy pointed out that best resolution was obtained at pH?2.5 for five racemates using low percentages of HS-γ-CD, while SBE-β-CD was the most successful chiral selector offering acceptable resolution for all the six racemates, with the best separation at low pH values and at higher %CD within 10-min runtime. Regression study showed that the linear model shows a significant lack of fit for all chiral selectors, anticipating that higher orders of the factors are most likely to be present in the equation with possible interactions.
- Abdel-Megied, Ahmed M.,Hanafi, Rasha S.,Aboul-Enein, Hassan Y.
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p. 165 - 176
(2017/11/27)
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- HPLC method for separating enantiomers of imidazole derivatives - Antifungal compounds
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The aim of this study was to test separation possibility of enantiomers of nine active substances belonging to imidazole derivatives: bifonazole, butoconazole, econazole, enilconazole, fenticonazole, isoconazole, miconazole, sertaconazole and tioconazole. The study was performed using HPLC method and the CHIRALCEL OJ column (10 μm; 250 × 4.6 mm), the mobile phase flow rate of 0.8 mL/min and detection at 220 nm. Mobile phases containing hexane and the following modifiers: alcohols (2-propanol, ethanol, methanol) and diethylamine were tested. At first isocratic elution was used but some enantiomers eluted after a long retention time and their peaks were asymmetrical and too wide. Therefore, a gradient elution was developed allowing to obtain satisfactory retention times and other parameters of enentioseparation of the compounds.
- Podolska, Marzena,Bia?ecka, Wanda,Kulik, Anna,Kwiatkowska-Puchniarz, Barbara,Mazurek, Aleksander
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p. 777 - 784
(2017/06/05)
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- METHOD FOR MANUFACTURING IMIDAZOLE COMPOUNDS AND SALTS AND PSEUDOPOLYMORPHS THEREOF
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The invention relates to a method for manufacturinc sertaconazole mononitrate. The invention also relates tcsertaconazole mononitrate that is characterized by it: particle size and to sertaconazole mononitrate monohydrate.
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Page/Page column 6
(2008/06/13)
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- METHOD FOR MANUFACTURING ENANTIOMERIC IMIDAZOLE COMPOUNDS
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The invention relates to a method for manufacturing R- (-) - sertaconazole mononitrate. The invention also relates to R- - (-)-sertaconazole mononitrate hemiacetonate.
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Page/Page column 10
(2008/06/13)
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- Synthesis and antimycotic activity of (benzo[b]thienyl)methyl ethers of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanol and of (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone oxime
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A new series of (benzo[b]thienyl)methyl ethers of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol and of (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone oxime were synthesized and tested for antifungal activity. Series design, synthesis, preliminary antimycotic data and structure-activity relationships are reported. 7-Chloro-3-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxymethyl] benzo[b]thiophene (8i, Sertaconazole, FI-7045, CAS 99592-32-2) and its nitrate were selected for further research.
- Raga,Moreno-Manas,Cuberes,Palacin,Castello,Ortiz
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p. 691 - 694
(2007/10/02)
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