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11.
Thevis M Lohmann W Schrader Y Kohler M Bornatsch W Karst U Schänzer W 《European journal of mass spectrometry (Chichester, England)》2008,14(3):163-170
The elucidation of the metabolism of new therapeutics is a major task for pharmaceutical companies and of great interest for drug testing laboratories. The latter in particular need to determine the presence or absence of drugs or their metabolic products in urine to test for a misuse of these compounds. Commonly, in vitro or animal models are used to mimic the human metabolism and produce potential targets in amounts allowing for method development. An alternative route based on electrochemical reactions of drugs was reported to allow for the generation of selected metabolites. The utility of this approach for doping control purposes was demonstrated with a novel class of anabolic agents termed selective androgen receptor modulators (SARMs). An arylpropionamide- derived drug candidate was subjected to electrochemical "metabolism" and a major phase-I- metabolite, resulting from the elimination of a substituted phenol residue as identified in in vitro experiments, was generated and characterised using liquid chromatography/nuclear magnetic resonance spectroscopy and high resolution/high accuracy mass spectrometry. The metabolite was included in routine doping control procedures based on liquid chromatography/tandem mass spectrometry and has served as a reference compound for 5000 doping control specimens. 相似文献
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Wiebke Engelmann Annette Zeyner Klaus D. Markuske Jörg R. Aschenbach 《Chromatographia》2009,70(7-8):1207-1213
In the intestine, microbial protein degradation to histamine and other biologically active amines is believed to be relevant to the health of species. An LC method with fluorescence detection has been developed for analysis of histamine, phenylethylamine, isoamylamine, putrescine, cadaverine, tyramine, and spermidine. After pre-column derivatisation with 9-fluorenylmethyl chloroformate, amines were separated on a reversed-phase C18 polyamine column with a mobile phase gradient. Validation of the method included calibration experiments, determination of amine recovery, and repeatability tests. The method proved especially useful for detection of histamine, phenylethylamine, putrescine, and cadaverine at relevant concentrations in caecum cultures from horses. The limits of quantification for these four amines ranged between 80 nM (histamine) and 400 nM (phenylethylamine). 相似文献
14.
The metabolism of the selective estrogen receptor modulator toremifene was simulated in an on-line electrochemistry/enzyme
reactor/liquid chromatography/mass spectrometry system. To simulate the oxidative phase I metabolism, toremifene was oxidized
in an electrochemical (EC) flow-through cell at 1,500 mV vs. Pd/H2 to its phase I metabolites, some of which are reactive quinoid species. In the presence of glutathione-S-transferase (GST), these quinoid compounds react with glutathione, which is also the common detoxification mechanism in the
body. While reacting with glutathione, the chlorine atom is eliminated from the toremifene moiety. Due to higher conversion
rates, GST supplied in continuous flow proved to be more efficient than using immobilized GST on magnetic microparticles.
In the absence of GST, not all GSH adducts are formed, proving the necessity of a phase II enzyme to simulate the complete
metabolic pathway of xenobiotics in an on-line EC/LC/MS system.
Figure Mass voltammogram of toremifene 相似文献
15.
Wiebke Germer Timo Stalling Uwe Kramer Wolfgang Saak Jürgen Martens 《Heteroatom Chemistry》2014,25(1):20-27
Starting with thiazolines, an important class of heterocyclic imines, a novel rearrangement reaction of corresponding N‐acyliminium ions is described. Furthermore, a new class of heterobicyclic compounds arylated at a single bridgehead atom is obtained diastereospecifically. 相似文献
16.
Jahn S Lohmann W Bomke S Baumann A Karst U 《Analytical and bioanalytical chemistry》2012,402(1):461-471
In the present study, a method for the analysis of reactive metabolites via liquid chromatography (LC) with inductively coupled
plasma–mass spectrometry (MS) was developed. A ferrocenyl-modified glutathione (GSH) reagent, consisting of GSH and succinimidyl-3-ferrocenylpropionate,
was synthesized. Derivatization of the tripeptide was performed at the N-terminus, leaving the nucleophilic thiol group vacant
for the attack of electrophilic compounds. The potential of ferrocenylpropionate (FP)-GSH as a trapping agent for reactive
metabolites was investigated using an electrochemical flow-through cell for metabolism simulation coupled online to a LC system
with electrospray ionization mass spectrometric detection. The pharmaceuticals amodiaquine, an antimalarial agent, and clozapine,
an antipsychotic compound, served as model substances. By proving the successful adduct formation between the reactive metabolite
and ferrocene-labeled GSH, it could be shown that FP-GSH is an effective trapping agent which eases routine reversed-phase
LC analyses. In contrast to GSH, which is usually used for the conjugation of reactive metabolites and where the resulting
adducts often show no or only very little retention, FP-GSH facilitates the detection of the corresponding metabolite adducts
due to higher retention times. 相似文献
17.
Many experiments and simulations of packings of monodisperse hard spheres report a dominance of the face-centered cubic structure in the hexagonally close-packed limit, even though it has no significant energetic or entropic gain over other close-packed configurations. Combining simulations and experiments, we demonstrate that a simple mechanical instability which occurs during the packing process may play an important role in selecting the face-centered cubic structure over other close-packed alternatives. Our argument is supported by detailed quantitative analyses of key configurations in sphere packings and highlights the importance of the packing dynamics. The proposed mechanism is elementary and should therefore play a role in a wide range of sphere systems. 相似文献
18.
TH van der Loop MR Panman S Lotze J Zhang T Vad HJ Bakker WF Sager S Woutersen 《The Journal of chemical physics》2012,137(4):044503
We study the structure and reorientation dynamics of nanometer-sized water droplets inside nonionic reverse micelles (water/Igepal-CO-520/cyclohexane) with time-resolved mid-infrared pump-probe spectroscopy and small angle x-ray scattering. In the time-resolved experiments, we probe the vibrational and orientational dynamics of the O-D bonds of dilute HDO:H(2)O mixtures in Igepal reverse micelles as a function of temperature and micelle size. We find that even small micelles contain a large fraction of water that reorients at the same rate as water in the bulk, which indicates that the polyethylene oxide chains of the surfactant do not penetrate into the water volume. We also observe that the confinement affects the reorientation dynamics of only the first hydration layer. From the temperature dependent surface-water dynamics, we estimate an activation enthalpy for reorientation of 45 ± 9 kJ mol(-1) (11?±?2 kcal mol(-1)), which is close to the activation energy of the reorientation of water molecules in ice. 相似文献
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20.
Prof. Dr. Cosima Stubenrauch Dr. Angelika Menner Prof. Alexander Bismarck Dr. Wiebke Drenckhan 《Angewandte Chemie (International ed. in English)》2018,57(32):10024-10032
Emulsions, foams, and foamed emulsions have been used successfully as templates for the synthesis of macroporous polymers. Based on this knowledge this Minireview presents strategies to use, optimise, and upscale these templating methods to synthesise tailor‐made porous polymers. The uniqueness of such polymers lies in the ability to tailor their structures and, therefore, their properties. However, systematic studies on structure–property relations are lacking mainly because the templating scientific community is “split into two”: the polydisperse and monodisperse camps. Thus, it is time to build a bridge between the camps, that is, to synthesise porous polymers with very different structures from the same precursors to determine the relationship between the structure and the properties. 相似文献