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Synthesis of Highly Substituted γ‐Butyrolactones by a Gold‐Catalyzed Cascade Reaction of Benzyl Esters
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Maria Camila Blanco Jaimes Alexander Ahrens Daniel Pflästerer Dr. Matthias Rudolph Prof. Dr. A. Stephen K. Hashmi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(1):427-433
Easily accessible benzylic esters of 3‐butynoic acids in a gold‐catalyzed cyclization/rearrangement cascade reaction provided 3‐propargyl γ‐butyrolactones with the alkene and the carbonyl group not being conjugated. Crossover experiments showed that the formation of the new C?C bond is an intermolecular process. Initially propargylic–benzylic esters were used, but alkyl‐substituted benzylic esters worked equally well. In the case of the propargylic–benzylic products, a simple treatment of the products with aluminum oxide initiated a twofold tautomerization to the allenyl‐substituted γ‐butyrolactones with conjugation of the carbonyl group, the olefin, and the allene. The synthetic sequence can be conducted stepwise or as a one‐pot cascade reaction with similar yields. Even in the presence of the gold catalyst the new allene remains intact. 相似文献
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Leonor Contreras Ignacio Villarroel Camila Torres Roberto Rozas 《Molecules (Basel, Switzerland)》2021,26(6)
Doxorubicin (DOX), a recognized anticancer drug, forms stable associations with carbon nanotubes (CNTs). CNTs when properly functionalized have the ability to anchor directly in cancerous tumors where the release of the drug occurs thanks to the tumor slightly acidic pH. Herein, we study the armchair and zigzag CNTs with Stone–Wales (SW) defects to rank their ability to encapsulate DOX by determining the DOX-CNT binding free energies using the MM/PBSA and MM/GBSA methods implemented in AMBER16. We investigate also the chiral CNTs with haeckelite defects. Each haeckelite defect consists of a pair of square and octagonal rings. The armchair and zigzag CNT with SW defects and chiral nanotubes with haeckelite defects predict DOX-CNT interactions that depend on the length of the nanotube, the number of present defects and nitrogen doping. Chiral nanotubes having two haeckelite defects reveal a clear dependence on the nitrogen content with DOX-CNT interaction forces decreasing in the order 0N > 4N > 8N. These results contribute to a further understanding of drug-nanotube interactions and to the design of new drug delivery systems based on CNTs. 相似文献
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Jadriane A. Xavier Thaissa L. Silva Eduardo Caio Torres-Santos Camila Calado de Vasconcelos Anastacio Boane Ricardo Alexandre dos Santos Andre Felippe A. Xavier Marília O.F. Goulart 《Current Opinion in Electrochemistry》2021
This review discusses the state of the art, challenges, and perspectives in recent applications of nitroaromatics and nitroheteroaromatics, which are redox-bio-activated drugs or leads, in Medicinal Chemistry. It deals mainly with the electrochemical approach toward the electron transfer-based molecular mechanisms of drug action, drug design, estimation and measurement of redox potentials, correlation of physicochemical and pharmacological data, and electrochemical studies of the main representatives of nitro-containing prodrugs, along with approaches to combat their toxicity issues, aiming at a better therapeutic profile. Electrochemical investigation plays essential roles, being strategic in the design and discovery of potential medicines. 相似文献
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Camila L. de Camargo Letícia S. ShiromaGabriela F. Giordano Angelo L. GobbiLuis C.S. Vieira Renato S. Lima 《Analytica chimica acta》2016
This paper addresses an important breakthrough in the deployment of ultra-high adhesion strength microfluidic technologies to provide turbulence at harsh flow rate conditions. This paper is only, to our knowledge, the second reporting on the generation of high flow rate-assisted turbulence in microchannels. This flow solves a crucial bottleneck in microfluidics: the generation of high throughput homogeneous mixings. We focused on the fabrication of bulky polydimethylsiloxane (PDMS) microchips (without any interfaces) rather than the laborious surface modifications that were employed in the first reporting about turbulence-assisted microfluidics. The fabrication is cleanroom-free, simple, low-cost, fast, solventless, and bondless requiring only a laboratory oven. More specifically, our method relies on the shaping of a nylon scaffold, cure of PDMS with embedded nylon, and removal of this scaffold. The scaffold was obtained by manually wrapping nylon threads. The withdrawing out of the scaffold was completed in few seconds using only a plier. Such microchannels endured flow rates of up to 60.0 mL min−1 with a strikingly low elastic deformation. The importance in producing turbulence into microscale channels was successfully shown in liquid-liquid extractions. The great energy dissipation rate relative to the turbulence created high throughput and efficient extractions in microfluidics for the first time. The residence time was only 0.01 s at 25.0 mL min−1 (total flow rate of the immiscible phases). In addition, the partition coefficient determined in a single run was similar to that obtained by the conventional batch shake-flask method that was realized in triplicate. 相似文献
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Pedro Marcos Frugeri Camila Marchioni Ayla Campos do Lago Célio Wisniewski 《Analytical letters》2018,51(10):1492-1504
This work proposes a flow injection analysis system for sulfaguanidine determination in pharmaceutical and food samples. The method was based on the reaction of sulfaguanidine with nitronium ion to produce a colored complex whose absorbance was measured at 545?nm. The flow injection analysis system’s significant parameters were checked by a fractional factorial design 27–2 and optimization by a Doehlert matrix. The flow injection analysis system shows optimum values at 0.28, 2.00, and 0.11% (w/v) for N-naphtil ethylenediamine, ammonium sulfamate, and sodium nitrite concentrations, respectively. The possible interferents present in pharmaceutical and food samples were assessed by a multivariate technique and depicted on probability charts, indicating no significant interferences at the 95% level of confidence interval. The method showed detection and quantification limits of 0.012 and 0.039?mg?L?1, an analytical frequency of 30 readings h?1 and precision always lower than 5.0% expressed as the relative standard deviation. The obtained results were in accordance with those obtained by high-performance liquid chromatography. 相似文献
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de Oliveira Cristina Soltovski Bet Camila Delinski Bisinella Radla Zabian Bassetto Waiga Lucas Henrique Colman Tiago André Denck Schnitzler Egon 《Journal of Thermal Analysis and Calorimetry》2018,133(3):1491-1498
Journal of Thermal Analysis and Calorimetry - Samples of potato starch (PS), sweet potato starch (SPS) and their binary mixtures, with moisture levels of 10, 15 and 20% (db), were submitted to... 相似文献
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A simple and high‐resolution HPLC‐PDA method for simultaneous quantification of local anesthetics in in vitro buccal permeation enhancement studies
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Renê O. Couto Camila Cubayachi Renata F. V. Lopez Cristiane M. de Gaitani Vinícius Pedrazzi Osvaldo de Freitas 《Biomedical chromatography : BMC》2016,30(6):857-866
A simple, isocratic, high‐resolution and prompt HPLC‐PDA method was developed and validated for the simultaneous quantification of prilocaine (PCL) and lidocaine (LCL) hydrochlorides in in vitro buccal iontophoresis‐driven permeation studies. A reversed‐phase C18 column (250 mm x 4.6 mm, 3μm, 110Å) was used for the chromatographic separation. The mobile phase contained acetonitrile: 0.1M sodium phosphate buffer, pH 7.0 (1:1, v/v), plus 0.05% (v/v) diethylamine. The isocratic flow rate was set at 1 mL/min and the detection wavelength was 203 nm. PCL and LCL eluted in 8.9 min and 13 min, respectively, and the system suitability parameters varied within an acceptable range. The method was selective, sensitive, precise, accurate and robust, producing a linear plot at the concentration range of 0.25 to 10 µg/mL. The application of this method was demonstrated by a significant enhancement of the permeation of PCL and LCL with the application of iontophoresis (1 mA/cm2 per 1 h) through isolated porcine esophageal epithelium. The amount of the drug retained in the epithelium also increased with the application of an electrical current. Copyright © 2015 John Wiley & Sons, Ltd. 相似文献
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This paper proposes to obtain homogeneous and stable blends of oligo(9,9-dioctylfluorene)-co-phenylene (OF), a conjugated oligomer with strong tendency of formation of excimers in the solid state, and nitrile rubber (NBR). This rubber protection reduces the formation of polymer excimers in the films. The fluorene oligomer was synthesized via Suzuki reaction and incorporated in the nitrile rubber. The films were formed by spin coating and casting techniques on the proportions of 1, 5, 10, 20 and 50 % (w/w) of OF in the nitrile rubber (NBR). The structural, optical and thermal properties of the films were evaluated with infrared, UV–Vis, fluorescence and thermogravimetry, respectively. The nitrile rubber proved to be essential for the preparation of homogeneous and stable films, since it was not possible to obtain films with only fluorene using the above-mentioned techniques. Furthermore, luminescent properties of OF are unchanged and the excimers formation in the solid state decrease suggesting the efficiency of nitrile rubber as the matrix for making films. 相似文献