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At least 19 recordsLinked to original sources
PubMed2001

[Synthesis and pharmacologic action of chiral fomocaine ((4-[2-methyl-3-(morpholin-4-yl)propyl)benzyl)-phenyl-ether and (4-(1-methyl-3-(morpholin-4-yl)propyl]benzyl)-phenyl-ether). 13. Synthesis of new compounds with local anesthetic action].

The syntheses of two chiral fomocaines namely rac ((4-[2-methyl-3-(morpholin-4-yl)propyl]-benzyl)-phenyl-ether (O/G 3) and rac (4-[1-methyl-3-(morpholin-4-yl)propyl]benzyl)-phenyl-ether) (O/G 5) are reported. These compounds are part of a new research program concerning the relation between chirality and local anaesthetic activity in the group of fomocaines. The yield over five steps is in the range of 9% (O/G 3) up to 19.2% (O/G 5). The racemates were resoluted via the diastereomeric salts formed with (+)- or (-)-camphersulfonic acid. The chromatographic resolution in analytical scale is successful using a Daicel OD-column. The enantiomers are stable. The surface anaesthesia of the racemates as well as of the enantiomeres is weaker in comparison with fomocaine. The rate of tissue irritation is higher. The LD50 (mouse i.v.) is in the range between 290-390 mg/kg, while fomocaine shows a LD50 value of 175 mg/kg.

Anesthetics, Local↗
PubMed1975

The metabolism of phenyl o-(2-N-morpholinoethoxy)-phenyl ether hydrochloride in the rabbit and rat.

1. Urinary and faecal excretion of radioactivity in 120 h after oral administration of [U-14-C]phenyl o-(2-N-morpholinoethoxy)phenyl ether hydrochloride (200 mg/kg) were 92 and 3% dose in the rabbit, and 60 and 35% in the rat. 2. Urinary metabolites were produced by aromatic hydroxylation and aryl alkyl ether bond cleavage. Some evidence for formation of dioxomorpholino, oxohydroxymorpholino, and ethanolamino derivatives of the drug was obtained. 3. The aromatic hydroxylation product, p-hydroxyphenyl o-(2-N-morpholinoethoxy)phenyl ether hydrochloride had vasopressor activity comparable with the parent compound, but with shorter duration of action.

Animals↗
PubMed1957

Some actions of substituted choline phenyl ethers, particularly of choline 2:6-xylyl ether.

Marked nicotine-like stimulant properties are possessed by choline phenyl ether and choline o-tolyl ether, and to a decreasing extent by choline 2:6-xylyl ether and choline 2:4:6-mesityl ether. The compounds all show neuromuscular blocking properties, which are of short duration and pass from mainly decamethonium-like to mainly curare-like as more methyl groups are added to the phenyl nucleus. This series of compounds also possesses muscarinic, weak anti-adrenaline and vasodilator properties, as well as long-lasting local anaesthetic effects in the two compounds tested by intradermal injection.

Choline↗
PubMed1987

Substituted arylmethyl phenyl ethers. 1. A novel series of 5-lipoxygenase inhibitors and leukotriene antagonists.

A series of new substituted arylmethyl phenyl ethers has been prepared. These compounds were tested as inhibitors of 5-lipoxygenase (5-LO) in rat neutrophils, in vitro antagonists of leukotriene-induced contraction of guinea pig (GP) lung parenchymal strips, and inhibitors of slow reacting substance of anaphylaxis (SRS-A) mediated bronchospasm in the GP in vivo. Most representatives of this new class of potential antiallergic/antiinflammatory agents showed potent inhibition of 5-LO activity in rat PMNs. The most potent compound, 2-[[3-(1-hydroxyhexyl)phenoxy]-methyl]quinoline (33), had an I50 of 0.12 microM in the rat PMN 5-LO assay and an I50 of 3.6 microM in the leukotriene-induced contraction of GP lung parenchymal strips, and it also showed 91% inhibition of SRS-A-mediated bronchospasm in the GP in vivo at 10 mg/kg, administered intraduodenally. Some of the compounds in this series were also leukotriene antagonists in vitro, and several of them showed in vivo activity against SRS-A-mediated bronchospasm in the GP.

Animals↗
PubMed2006

Structure-activity relationships for a novel series of thiazolyl phenyl ether derivatives exhibiting potent and selective acetyl-CoA carboxylase 2 inhibitory activity.

Structure-activity relationships for a recently discovered thiazolyl phenyl ether series of acetyl-CoA carboxylase (ACC) inhibitors were investigated. Preliminary efforts to optimize the series through modification of the distal aryl ether moiety of the lead scaffold resulted in the identification of compounds exhibiting low-nanomolar potency and isozyme-selective ACC2 activity.

Acetyl-CoA Carboxylase↗
PubMed2003

Phenyl ethers from cultured lichen mycobionts of Graphis scripta var. serpentina and G. rikuzensis.

Spore-derived mycobionts of the lichen Graphis scripta var. serpentina and G. rikuzensis were cultivated on a malt-yeast extract medium supplemented with 10% sucrose and their metabolites were investigated. 3,3'-Dihydroxy-5,5'-dimethyldiphenyl ether was isolated from the cultures of the mycobionts of G. scripta var. serpentina, while a new phenyl ether, rikuzenol, along with two known diphenyl ethers, violaceol-I and violaceol-II, were isolated from those of G. rikuzensis. The structure of the new compound was determined by spectroscopic methods. Violaceol-I was chemically synthesized and interconversion between violaceol-I and violaceol-II was proven.

Lichens↗
PubMed1996

Determination of biogenic halogenated methyl-phenyl ethers (halogenated anisoles) in the picogram m(-3) range in air.

Halogenated anisoles (methyl-phenyl ethers) appear to be ubiquitous organic trace compounds in the environment. An analytical method is presented for analyzing the altogether 134 congeners of chloro-, bromo- and mixed bromochloro-anisoles on an isomer-specific basis in air. High volume sampling (20 m(3) per hour) is carried out by adsorption, using a mixture of silica gel 60 and ENVI-Carb. The preseparation of the anisoles is achieved by NP-LC on Florisil (a magnesium silicate). The interference by volatile n-alkyl nitrates in the electron-capture detection can be avoided by a LC-preseparation on a carboneous phase. The isomer-specific separation and detection is performed by HRGC-ECD and HRGC-MS-SIM. A structure-specific systematic numbering of the 134 congeners of the chloro-, bromo- and bromochloro-anisoles is suggested. The retention data are given of 16 chloroanisoles, 10 bromoanisoles and 27 bromo-chloroanisoles on three stationary phases with different polarity.

Journal Article↗
PubMed1996

Reactions of Allyl Phenyl Ether in High-Temperature Water with Conventional and Microwave Heating.

In a systematic study, allyl phenyl ether (1) was heated in water for 1 h at temperatures of 180 degrees C and above. Parallel experiments were conducted with a conventionally heated autoclave and a recently developed microwave batch reactor. Relatively modest temperature differences resulted in diverse product distributions, and these were independent of the method of heating. Maximum conversion of 1 to 2-allylphenol occurred at 200 degrees C (56%) and to 2-methyl-2,3-dihydrobenzofuran at 250 degrees C (72%). Although 2-(2-hydroxyprop-1-yl)phenol comprised less than 1% of the product mixture at both 180 and 260 degrees C, it accounted for 37% at 230 degrees C. The reaction sequence was investigated by heating intermediates individually at selected temperatures up to 290 degrees C. Hydration of 2-allylphenol to 2-(2-hydroxyprop-1-yl)phenol was partially reversible. The work showed that high-temperature water constitutes an environmentally benign alternative to the use of acid catalysts or organic solvents and offers scope for interconversion of alcohols and alkenes.

Journal Article↗
PubMed2000

Claisen rearrangement of allyl phenyl ether and its sulfur and selenium analogues on electron impact

The electron impact (EI) mass spectrum of allyl phenyl ether (1) includes an ion at m/z 106 that is formed mainly by the loss of CO from the molecular ion, as supported by high resolution and MS/MS data. The formation of the [M - CO](+) ion from 1 can be explained in terms of the Claisen rearrangement of 1 after ionization in the ion source of the mass spectrometer. Similarly, allyl phenyl sulfide (2) and allyl phenyl selenide (3) showed characteristic ions corresponding to [M - CH(3)](+), [M - XH](+) (X = S or Se) and [M - C(2)H(4)](+.), and the formation of these ions are explained via Claisen rearrangement of 2 and 3 in the ion source of the mass spectrometer resulting in a mixture of rearrangement products. The formation of molecular ions of 2-allyl thiophenol and 2-allyl selenophenol as intermediates, that cannot be isolated as the neutrals from the solution phase Claisen rearrangement of 2 and 3, respectively, is clearly indicated in the gas phase. The mass spectra of the rearrangement products obtained from the solution phase reaction were also consistent with the proposal of formation of these products in the ion source of the mass spectrometer. The formation of characteristic fragment ions attributed to the Claisen rearrangement products are also evident in the collision induced dissociation spectra of the corresponding molecular ions. Copyright 2000 John Wiley & Sons, Ltd.

Journal Article↗
PubMed2002

Synthesis and structural characterization of Cu(I) and Ni(II) complexes that contain the bis[2-(diphenylphosphino)phenyl]ether ligand. Novel emission properties for the Cu(I) species.

The pseudotetrahedral complexes [Cu(NN)(DPEphos)]BF(4), where DPEphos = bis[2-(diphenylphosphino)phenyl]ether and NN = 1,10-phenanthroline (1), 2,9-dimethyl-1,10-phenanthroline (2), 2,9-di-n-butylphenanthroline (3), or two dimethylcyanamides (4), and NiCl(2)(DPEphos) (5) have been synthesized and structurally characterized by X-ray crystallography and their solution properties examined by use of a combination of cyclic voltammetry, NMR spectroscopy, and electronic absorption spectroscopy. Complexes 1-4 possess a reversible Cu(II)/Cu(I) couple at potentials upward of +1.2 V versus Ag/AgCl. Compounds 1-3 exhibit extraordinary photophysical properties. In room-temperature dichloromethane solution, the charge-transfer excited state of the dmp (dbp) derivative exhibits an emission quantum yield of 0.15 (0.16) and an excited-state lifetime of 14.3 mus (16.1 mus). Coordinating solvents quench the charge-transfer emission to a degree, but the photoexcited dmp complex 2 retains a lifetime of over a microsecond in acetone, methanol, and acetonitrile.

Journal Article↗
PubMed2000

3-Chloropropyl and 4-chlorobutyl phenyl ethers as sources of 1, 3-dilithiopropane and 1,4-dilithiobutane: sequential reaction with carbonyl compounds

The reaction of 3-chloropropyl and 4-chlorobutyl phenyl ethers (1) with lithium powder and a catalytic amount of DTBB (5% molar) in THF at -78 degrees C followed by successive treatment with a carbonyl compound [R(1)R(2)CO = Bu(t)CHO, Me(2)CO, (CH(2))(5)CO, (-)-menthone] at -78 to 20 degrees C and, after 1.5 h at this temperature, with a second one [R(3)R(4)CO = Bu(t)CHO, PhCHO, Me(2)CO, MeCOPr(n), (CH(2))(5)CO, (-)-menthone] at -78 degrees C leads, after hydrolysis with water, to the corresponding 1,5- and 1, 6-diols (2). Because of the competition of two different reductive cleavages, 1,4- and 1,5-diols 3 were also obtained as side-reaction products.

Journal Article↗
PubMed2002

Use of nonionic poly(ethylene glycol) p-isooctyl-phenyl ether (Triton X-1 00) surfactant mobile phases in the thin-layer chromatography of heavy-metal cations.

The analytical potential of poly(ethylene glycol) p-isooctyl-phenyl ether (Triton X-100), a nonionic surfactant, is used as a mobile phase in the thin-layer chromatographic separation of heavy-metal cations. The surfactant concentration below its critical micellar concentration (CMC) as well as above the CMC value is used to investigate the migrational behavior of some heavy-metal ions on silica gel layers. The mobility of the metal ions is found to change marginally with the increase of surfactant concentration from 0.001M (below CMC) to 0.1M (above CMC). The influence of the pH of the medium, nonelectrolyte organic (urea and alkanols), and inorganic electrolyte (NaCI) additives in the surfactant containing mobile phase on the mobility of heavy metals on the silica gel layer is examined. For separating metal ions, surfactant must be used in the presence of buffers. Triton X-100 (0.02M) at pH 2.3 is found to be the best mobile phase for the separation of heavy-metal cations. In general, the presence of alcohol in aqueous surfactant solutions results in a decrease in the mobility of metal ions. Besides Cu2+ and Fe3+, all of the metal ions show a trend of increasing the retardation factor beyond a minima at 0.1 or 0.3M of added urea or NaCl. The proposed method is successfully applied for the simultaneous detection of Zn2+ and Cd2+ from a spiked human blood sample.

Journal Article↗
PubMed2001

Halogenated methyl-phenyl ethers (anisoles) in the environment: determination of vapor pressures, aqueous solubilities, Henry's law constants, and gas/water- (Kgw), n-octanol/water- (Kow) and gas/n-octanol (Kgo) partition coefficients.

Halogenated methyl-phenyl ethers (methoxybenzenes, anisoles) are ubiquitous organics in the environment although they are not produced in industrial quantities. Modelling the fate of organic pollutants such as halogenated anisoles requires a knowledge of the fundamental physico-chemical properties of these compounds. The isomer-specific separation and detection of 60 of the 134 possible congeners allowing an environmental fingerprinting are reported in this study. The vapor pressure p0(L) of more than 60 and further physico-chemical properties of 26 available congeners are given. Vapor pressures p0(L), water solubilities S(L)W, and n-octanol/water partition coefficients Kow were determined by capillary HR-GC (High Resolution Gas Chromatography) on a non-polar phase and by RP-HPLC (Reversed Phase High Performance Liquid Chromatography) on a C18 phase with chlorobenzenes as reference standards. From these experimental data the Henry's law constants H, and the gas/water Kgw and gas/n-octanol Kgo partition coefficients were calculated. We found that vapor pressures, water solubilities, and n-octanol/water partition coefficients of the halogenated anisoles are close to those of the chlorobenzenes. A similar environmental fate of both groups can, therefore, be predicted.

Anisoles↗