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Fluorine Compounds (1):
Recent article
Fluorine Compounds
Organic Letters (13)7 2011
Abstract
The (hetero)aromatic trifluoromethyl group is present in many biologically active molecules and is generally considered to be chemically stable. In this paper, a convenient one-step synthesis of C-C linked aryl-heterocycles or heteroaryl-heterocycles in good to excellent yields via t...
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PMID: 21381681
PDF is available here.
PDF is available here.
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Abstract
An efficient short protocol for the preparation of N-perfluoroacylated glycals of neuraminic acid, by simple short treatment of differently protected N-acetylneuraminic acid with perfluorinated anhydrides in acetonitrile at 135 degrees C, is reported, together with a rationalitazion of the reaction...
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PMID: 20559590
PDF is available here.
PDF is available here.
Abstract
Interactions between dissolved peat humic acid and two structurally dissimilar organofluorine compounds, perfluoro-2-naphthol and perfluoro-octanoic acid, are probed using a novel (1)H{(19)F} Nuclear Magnetic Resonance (NMR) Spectroscopy technique based on the Saturation Transfer Difference (STD) ex...
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PMID: 20568693
PDF is available here.
PDF is available here.
Abstract
Perfluorinated compounds (PFCs) are globally distributed persistent environmental contaminants. This study provides temporal trends as well as large-scale spatial trends of PFC concentrations in threatened juvenile loggerhead sea turtles near or from Florida Bay (FL Bay), Cape Canaveral (FL), Charle...
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PMID: 20521819
PDF is available here.
PDF is available here.
Journal of Hazardous Materials (178)1-3 2010
Abstract
We investigated the synergetic effect of La and F on the visible light photocatalytic activity of TiO(2) catalysts. La(2)O(3)/TiO(2-x)F(x) photocatalysts were prepared by a simple sol-gel process using tetrabutyl titanate (TBT), La(NO(3))(3) and NH(4)F as precursors. XPS results revealed that La(2)O...
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PMID: 20149531
PDF is available here.
PDF is available here.
Abstract
New biphasic conditions for the palladium-catalyzed direct arylation of electron-poor fluorinated arenes have been developed. Taking advantage of biphasic chemistry, the use of an immiscible mixture of water and an organic solvent allows complete solubilization of all components of the system, enabl...
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PMID: 20380389
PDF is available here.
PDF is available here.
Abstract
The study in 727 workers exposed to inorganic fluorine compounds revealed through ultrasound densitometry changes in fluorine excretion and bone tissue density in accordance with the length of service, through markers of bone destruction and synthesis features of bone remodelling were specified.
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PMID: 20402218
PDF is available here.
PDF is available here.
Abstract
Workers in electrolysis workshops of aluminium plants demonstrate changes in intracardial hemodynamics and left ventricle diastolic function, heart remodelling to concentric and excentric hypertrophy, more in individuals with chronic occupational fluorine intoxication.
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PMID: 20402217
PDF is available here.
PDF is available here.
Abstract
We review the historical and recent developments of organofluorine biotransformation in microorganisms and highlight the possibility of using microbes as models of fluorinated drug metabolism in mammals....
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PMID: 19629474
PDF is available here.
PDF is available here.
Abstract
Individual differences in 5-FU metabolism are mainly attributed to individual differences in the activity of DPD, an enzyme that can metabolize more than 85% of 5-FU. Because urinary uracil is a reflection of DPD activity, it is measured to predict and prevent the occurrence of side effects caused b...
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PMID: 19381049
PDF is available here.
PDF is available here.
Journal of Physical Chemistry B (112)40 2008
Abstract
Glasses belonging to the Na(2)O-CaO-P(2)O(5)-SiO(2) system and modified by CaF(2) substitution for CaO and Na(2)O alternatively, were synthesized and characterized experimentally and computationally. The results of molecular dynamics simulations show that fluorine is almost exclusively bonded to mod...
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PMID: 18783268
PDF is available here.
PDF is available here.
Biophysical Journal (95)8 2008
Abstract
We recently demonstrated that the latter process can be prevented by the use of fluorinated surfactants, FTACs, that act as chaperones for MP insertion without partitioning in the membrane themselves. Here we combine the advantages of the chaperone-like ability of FTACs with the sensitivity of fluor...
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PMID: 18708456
PDF is available here.
PDF is available here.
Abstract
A silver- and Brönsted acid-free protocol for generating the (tricyclohexylphosphine)gold(I) cation from the corresponding azide complexes is disclosed. The gold(I) cations so liberated are trapped by complexation with octaethylporphyrin. The first structurally authenticated gold(I) porphyrin compl...
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PMID: 18780788
PDF is available here.
PDF is available here.
Abstract
Three unique diastereoisomers of 2,3,4,5-tetrafluorohexane have been prepared, compounds intermediate between hexane and perfluorohexane in their degree of fluorination, and they show very different conformational behaviour and physical properties.
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PMID: 18698469
PDF is available here.
PDF is available here.
ChemPhysChem (9)12 2008
Abstract
A velocity imaging technique combined with (2+1) resonance-enhanced multiphoton ionization (REMPI) is used to detect the primary Br((2)P(3/2)) fragment in the photodissociation of o-, m-, and p-dibromobenzene at 266 nm. The obtained translational energy distributions suggest that the Br fragments ar...
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PMID: 18624286
PDF is available here.
PDF is available here.
Abstract
We describe the synthesis of these fluorinated thin films using hexafluoropropene as starting material and discuss their properties. These coatings, applied to stainless steel, provide ideal substrates for Raman spectroscopy, when extremely low backgrounds are required. Raman spectroscopy measuremen...
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PMID: 18627194
PDF is available here.
PDF is available here.
Abstract
Abstract
Fluoropolymer plasma coatings have been investigated for application as stent coatings due to their chemical stability, conformability, and hydrophobic properties. The challenge resides in the capacity for these coatings to remain adherent, stable, and cohesive after the in vivo stent expansion, whi...
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PMID: 18616223
PDF is available here.
PDF is available here.
Abstract
We speculate that such structure hinders the energetically optimal orientation of the hydrophobic -CH(2)CF(3) terminals toward air, so that the (delta+)C-(F (delta-))(3) dipoles at the monolayer/water boundary yield a strong positive contribution to Delta V. In contrast, most of the unbounded by H-b...
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PMID: 18598061
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (73)15 2008
Abstract
We report the preparation of organotrifluoroborates bearing functional groups that can be manipulated at different stages of the synthetic route, exploiting the inertness of their carbon-boron bonds. The alkylation of 2,2-dicyanoethyltrifluoroborate with a variety of electrophiles and of (EWG)2CH2 w...
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PMID: 18588349
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (73)15 2008
Abstract
We have successfully accomplished the nucleophilic fluoroalkylation of alpha,beta-enones, arynes, and activated alkynes with fluorinated sulfones. It was found that for acylic alpha,beta-enones, although the reaction medium and the structure of the enones can all influence the regioselectivity of th...
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PMID: 18593187
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (73)14 2008
Abstract
A method for the nucleophilic trifluoromethylation of N-benzoylhydrazones using Me3SiCF3/AcONa has been described. The CN bond of the hydrazones is activated by difluoroboron group, which is introduced by means of boron trifluoride and allylsilane.
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PMID: 18558768
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (73)14 2008
Abstract
Nitrones derived from aromatic or aliphatic aldehydes or ketones react with hexafluoropropene (HFP) or 2H-pentafluoropropene (PFP) to give the respective fluorinated isoxazolidine derivatives in good yields with complete regioselectivity and moderate diastereoselectivity. Catalytic hydrogenolysis of...
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PMID: 18558769
PDF is available here.
PDF is available here.
Journal of Organic Chemistry (73)14 2008
Abstract
Difluoropiperidines attract considerable interest from organic and medicinal chemists, but their synthesis is often problematic. This paper describes a new synthetic pathway toward valuable 3,3-difluoropiperidines starting from suitable delta-chloro-alpha,alpha-difluoroimines. The latter imines can...
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PMID: 18547110
PDF is available here.
PDF is available here.
Abstract
A combination of the Langmuir-Blodgett and Langmuir-Schaefer techniques has been used to build a 1,2-dimyristoyl- sn-glycero-3-phosphocholine (DMPC) bilayer at a Au(111) electrode surface with hydrogen-substituted acyl chains in the top leaflet (solution side) and deuterium-substituted acyl chains i...
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PMID: 18543999
PDF is available here.
PDF is available here.
Abstract
The synthesis and colloidal study of a new class of low molecular weight organogelators is reported. Racemic propargylic alcohols with perfluoroaryl and nonfluorinated aryl rings are capable of forming gels in alkane liquids and/or silicone oil. A full colloidal characterization of alkane gels prepa...
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PMID: 18553992
PDF is available here.
PDF is available here.
Journal of Physical Chemistry B (112)28 2008
Abstract
We have analyzed the structure of solid-supported bilayers composed of 1,2-dipalmitoyl- sn-glycero-3-phosphocholine (DPPC) and of a DPPC analogue with 6 terminal perfluorinated methylene units (F6-DPPC). Polarized attenuated total reflection Fourier-transform infrared spectroscopy indicates that for...
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PMID: 18563929
PDF is available here.
PDF is available here.
Abstract
Three types of 5alpha-androstane and ergostane analogues of brassinolide, containing a fluorine atom in either the 3alpha or the 5alpha positions or in 3alpha and 5alpha positions, were prepared using standard operations (reaction of 3beta-alcohols with (diethylamino)sulfur trifluoride, cleavage of...
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PMID: 18557605
PDF is available here.
PDF is available here.
Organic Letters (10)13 2008
Abstract
An expedient synthesis of a series of 2-pyrones, bearing a CF 3 group at the 6-position and aryl group at position 4, from readily available aryl-4,4,4-trifluorobutane-1,3-diones, PCl 5, and sodium diethyl malonate is described.
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PMID: 18537252
PDF is available here.
PDF is available here.
Abstract
We aim to demonstrate that high-resolution optical coherence tomography (HR-OCT) can close this gap. Rabbit corneas were exposed ex vivo to 2.5% hydrofluoric acid (HF) solution, and microstructural changes were monitored in the time domain by OCT imaging. HF application and penetration resulted in s...
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PMID: 17869429
PDF is available here.
PDF is available here.
Biophysical Journal (94)11 2008
Abstract
We recently applied fluorinated nondetergent surfactants that act as chemical chaperones. The ideal chaperone surfactant would 1), maintain the MP in solution; 2), minimally perturb the MP's structure; 3), dissociate from the MP during membrane insertion; and 4), not partition into the lipid bilayer...
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PMID: 18310255
PDF is available here.
PDF is available here.
Abstract
We analyzed 14 PFCs (seven were detected in more than 75% of samples), 10 PBDEs (only BDE 47 was detected), and 27 OCs, including 12 polychlorinated biphenyl (PCB) congeners (14 OCs were detected). Median total PFC concentration was higher than median total OC concentration (43 vs 39 ng/g wet wt). P...
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PMID: 18229973
PDF is available here.
PDF is available here.
Abstract
Diisopropylsilyl ethers were activated with N-bromosuccinimide, and reacted with a fluorous-tagged alcohol, to yield tethered substrates for ring-closing metathesis reactions.
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PMID: 18452006
PDF is available here.
PDF is available here.
Abstract
A series of fluoroalkyl end-capped diblock copolymers of poly[2-(N,N-dimethylamino)ethyl methacrylate] (PDMAEMA or PDMA) and poly[2-(N,N-diethylamino)ethyl methacrylate] (PDEAEMA or PDEA) have been synthesized via oxyanion-initiated polymerization, in which a potassium alcoholate of 4,4,5,5,6,6,7,7,...
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PMID: 18376894
PDF is available here.
PDF is available here.
Abstract
For GC-MS analysis of delta-9-tetrahydrocannabinol (delta-9-THC), perfluoroacid anhydrides in combination with perfluoroalcohols are commonly used for derivatization. This reagent mixture is preferred because it allows simultaneous derivatization of delta-9-THC and its acid metabolite, 11-nor-delta-...
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PMID: 18205240
PDF is available here.
PDF is available here.
Abstract
Positive and negative electrospray mass spectrometry (MS), in-time and in-space MS(n) experiments, high-resolution and accurate mass measurements obtained with an Orbitrap, together with density functional theory calculations have been used to study the gas-phase ion chemistry of a series of fluorin...
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PMID: 18339558
PDF is available here.
PDF is available here.
Abstract
General reaction conditions were developed for the Pd(0)-catalyzed Suzuki-Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable a...
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PMID: 18380442
PDF is available here.
PDF is available here.
Abstract
We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinate...
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PMID: 18399658
PDF is available here.
PDF is available here.
Abstract
Fluorinated organo-silica gels doped with tetra-n-propylammonium perruthenate (TPAP) are excellent catalysts for the aerobic oxidative dehydrogenation of alcohols in supercritical CO2 (scCO2). Their activity and stability are subtly dictated by structure, depending on the degree of fluorination and...
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PMID: 18688355
PDF is available here.
PDF is available here.
Abstract
The synthesis of a series of 2-deoxy-2,2-dihaloglycosyl halides as potential alpha-glycosidase inactivators has been achieved via the halogenation of protected 2-fluoroglycal precursors. Direct chlorination of per-O-acetylated 2-fluoro-d-glucal and 2-fluoromaltal followed by basic deprotection yield...
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PMID: 18345685
PDF is available here.
PDF is available here.
Design, synthesis, and evaluation of trifluoromethyl ketones as inhibitors of SARS-CoV 3CL protease.
Abstract
A series of trifluoromethyl ketones as SARS-CoV 3CL protease inhibitors was developed. The inhibitors were synthesized in four steps from commercially available compounds. Three different amino acids were explored in the P1-position and in the P2-P4 positions varying amino acids and long alkyl chain...
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PMID: 18329272
PDF is available here.
PDF is available here.
Abstract
We have synthesized and evaluated a series of triaryl sulfonamide-based PTP1B inhibitors in which a difluoro-methylenephosphonate group of a potent lead has been replaced by potential bioisosteric replacements. Several mono- or di-charged compounds (8a, 8b, and 15a) were shown exhibit inhibitory act...
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PMID: 18372175
PDF is available here.
PDF is available here.
Abstract
The amount of water sorption tended to decrease as the number of the fluorine atoms in fluorinated monomers increased. Similar solubility was shown regardless of the type of fluorinated monomer. The use of fluorinated monomers for immersion in coffee allowed suppression of discoloration. In beta -ca...
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PMID: 18467789
PDF is available here.
PDF is available here.
Abstract
A series of 20 novel 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines were designed, synthesized, and screened in vitro for anti-inflammatory activity. These compounds were designed for evaluation as dual inhibitors of cyclooxygenases (COX-1 and COX-2) and lipoxygenases (LOX-5, LOX-12, a...
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PMID: 18272371
PDF is available here.
PDF is available here.
Abstract
We previously reported that the introduction of fluorine to the 4-position of 2-cyanopyrrolidine enhanced the DPP-IV inhibitory effect. In the present report, we examined the structure-activity relationship (SAR) of 2-cyano-4-fluoropyrrolidine with N-substituted glycine at the 1-position. We report...
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PMID: 18243000
PDF is available here.
PDF is available here.
Abstract
N-(3,5-Difluoro-4-hydroxyphenyl)benzenesulfonamide (4) and its derivatives 5-7 were prepared as putative bioisosteres of the previously reported aldose reductase inhibitors, which are the N-benzenesulfonylglycine derivatives I-IV. The in vitro aldose reductase inhibitory activity of the prepared com...
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PMID: 18267362
PDF is available here.
PDF is available here.
Abstract
Fluorinated Bi2WOs catalyst was synthesized by a simple hydrothermal process. The effects of fluorine doping on crystal structure, optical property, photoinduced hydrophilicity, surface acidity, and photocatalytic activity of the as-prepared sample were observed in detail. Fluorinated Bi2WOs present...
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PMID: 18409641
PDF is available here.
PDF is available here.
Journal of Physical Chemistry B (112)10 2008
Abstract
We developed a model called SM6T for predicting aqueous solvation free energies as a function of temperature for solutes composed of C, H, or O, and here we present solvation model 8 with temperature dependence (SM8T) for predicting the temperature dependence of aqueous free energies of solvation fo...
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PMID: 18281971
PDF is available here.
PDF is available here.
Abstract
A dual-level direct dynamic method is employed to study the reaction mechanisms of CF3CH2OCHF2 (HFE-245fa2; HFE-245mf) with the OH radicals and Cl atoms. Two hydrogen abstraction channels and two displacement processes are found for each reaction. For further study, the reaction mechanisms of its pr...
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PMID: 17705163
PDF is available here.
PDF is available here.
Abstract
Thirty-four newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids were synthesized from 1,2,3,4-tetrafluoro benzene and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB...
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PMID: 18078756
PDF is available here.
PDF is available here.
Abstract
The synthesis and antitumoral activity of ester and amide derivatives of 2-arylamino-6-trifluoromethyl-3-pyridinecarboxylic acids 8-58 is described. Trifluoromethylpyridine derivatives 8-58 were evaluated for their anticancer activity toward human tumoral cell lines by the National Cancer Institute...
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PMID: 18065230
PDF is available here.
PDF is available here.
Abstract
Synthesis and antiviral activity of the title fluoromethylenecyclopropane analogues 15a, 15b, 16a, and 16b is described. Methylenecyclopropane carboxylate was first transformed to 2,2-bis-hydroxymethylmethylenecyclopropane. Selective monoacetylation followed by introduction of fluorine gave 2-acetox...
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PMID: 18082410
PDF is available here.
PDF is available here.
Abstract
The stepwise and concerted pathways for the McLafferty rearrangement of the radical cations of butanal (Bu(+)) and 3-fluorobutanal (3F-Bu(+)) are investigated with density functional theory (DFT) and ab initio methods in conjunction with the 6-311+G(d,p) basis set. A concerted transition structure (...
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PMID: 17607719
PDF is available here.
PDF is available here.
European Journal of Pharmacology (580)1-2 2008
Abstract
We have started with the evaluation of various fluorinated indiplon derivatives. Binding affinities were determined in homogenates from newborn and adult rats suggesting an alpha1 preference of the reference compounds indiplon, zaleplon as well as for all newly synthesized indiplon derivatives. In h...
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PMID: 18035350
PDF is available here.
PDF is available here.
Abstract
A three step efficient strategy for the synthesis of substituted 5-nitropiperidones in high de, employing Michael addition of N-p-tolylsulfinyl beta-nitroamines to alpha,beta-unsaturated esters, hydrolysis of the sulfinyl group, and cyclization of the resulting free amines, has been developed. A ver...
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PMID: 18171078
PDF is available here.
PDF is available here.
Abstract
We report here the gas-phase mid-IR, near-IR, and visible vibrational spectra of perfluoropropionic, perfluorooctanoic, and perfluorononanoic acids using Fourier transform and cavity ring-down spectroscopy. The impetus for this work was to provide insight into the behavior of environmentally persist...
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PMID: 17927241
PDF is available here.
PDF is available here.
Biomaterials (29)2 2008
Abstract
A new strategy for the specific immobilization of proteins onto a solid support is presented. The immobilization is highly specific and efficient thanks to functionalized semifluorinated self-assembled monolayers (SAMs), thus reducing non-specific protein adsorption. Protein resistance does not excl...
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PMID: 17942149
PDF is available here.
PDF is available here.
Abstract
Because of the intrinsic properties of the fluorine atom, organic fluoride compounds have unique properties of particular importance in the pharmaceutical industry. The effect of fluorine is illustrated by selected examples of medicinal chemistry.
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PMID: 18435988
PDF is available here.
PDF is available here.
Abstract
Abstract
We detail in this article 1) the stereoselective preparation of the key intermediates heptosylglycals, 2) the development of a new fluorophosphorylation procedure allowing an excellent beta-gluco stereoselectivity with "all-equatorial" glycals, 3) the synthesis of the target ADP-2F-heptose, and 4) s...
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PMID: 18833547
PDF is available here.
PDF is available here.