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At least 163 records · Page 9Linked to original sources
PubMed2005

Structural effects on the beta-scission reaction of tertiary arylcarbinyloxyl radicals. The role of alpha-cyclopropyl and alpha-cyclobutyl groups.

A product and time-resolved kinetic study on the reactivity of tertiary arylcarbinyloxyl radicals bearing alpha-cyclopropyl and alpha-cyclobutyl groups has been carried out. Both the 1-cyclopropyl-1-phenylethoxyl (1.) and alpha,alpha-dicyclopropylphenylmethoxyl (2.) radicals undergo beta-scission to give cyclopropyl phenyl ketone as the major or exclusive product with rate constants higher than that measured for the cumyloxyl radical. It is proposed that in the transition state for beta-scission of 1. and 2., formation of the C=O double bond is assisted by overlap with the C-C bonding orbitals of the cyclopropane ring. With tertiary arylcarbinyloxyl radicals bearing alpha-cyclobutyl groups such as the 1-cyclobutyl-1-phenylethoxyl (4.) and 1-cyclobutyl-1-phenylpropoxyl (5.) radicals, the fragmentation regioselectivity is essentially governed by the stability of the radical formed by beta-scission. Accordingly, 4. undergoes exclusive C-cyclobutyl bond cleavage to give acetophenone, whereas with 5., competition between C-cyclobutyl and C-ethyl bond cleavage, leading to propiophenone and cyclobutylphenyl ketone in a 2:1 ratio, is observed.

Journal Article↗
PubMed2006

Studies of the condensation of sulfones with ketones and aldehydes.

[reaction: see text] The condensation of ketones or aldehydes with sulfones was shown to give a variety of products. Condensation of 2-methylcyclohexanone with dimethyl sulfone using potassium t-butoxide as base gave useful yields of 1,2-dimethylenecyclohexane. Under the same conditions, cycloheptanone, 3-methyl-2-butanone, and 2-butanone were converted to dienes. Remarkably, these reaction conditions converted acetophenone into p-terphenyl (10%) and (E)-1,4-diphenyl-3-penten-1-one (44%). Propiophenone was converted to 2'-methyl-p-terphenyl (61%). Using alpha-tetralone produced 1-methynaphthalene and naphthalene. No reaction took place with beta-tetralone. Using diethyl sulfone with alpha-tetralone lead to pure naphthalene. Condensation of isobutyraldehyde and dimethyl sulfone using potassium t-butoxide gave isoprene in low yield. Using benzaldehyde and benzyl phenyl sulfone in N,N-dimethylacetamide gave 1,2-diphenyl-1-phenylsulfonylethylene, N,N-dimethylcinnamide, and a complex condensation product. Only 1,2-diphenyl-1-phenylsulfonylethylene was obtained when the solvent was THF.

Journal Article↗
PubMed2006

Oxidations of secondary alcohols to ketones using easily recyclable bis(trifluoroacetate) adducts of fluorous alkyl iodides, CF3(CF2)(n-1)I(OCOCF3)2.

Reactions of commercial fluorous alkyl iodides RfnI (1-Rfn; Rfn = CF3(CF2)(n-1); n = 7, 8, 10, 12) with 80% H2O2 and trifluoroacetic anhydride give RfnI(OCOCF3)2 (2-Rfn; 97-89%). These efficiently oxidize aliphatic and benzylic secondary alcohols to the corresponding ketones (92-57%) in the presence of aqueous KBr and absence of organic or fluorous solvents. Bromide ion activates the reagents and/or generates a relay oxidant such as a functional equivalent of Br+. Oxidations are much more rapid (<30 min, 2-R(f8); <70 min, 2-R(f10)) than with other iodine(III) compounds under similar conditions. The coproducts 1-Rfn can be recovered by adding 3-5 volumes of methanol to the reaction mixtures. Fluorous/methanolic liquid/liquid (1-R(f8)) or solid/liquid (1-R(f10)) biphase systems result. The recovered 1-Rfn can be reoxidized to 2-Rfn and reused. Three cycles are conducted with 1-phenyl-1-propanol and 2-R(f10). The propiophenone yields range from 92% to 83% per cycle, and after the final cycle 59-57% of the original charge of the fluorous iodide species is recovered.

Journal Article↗
PubMed2005

Hollow colloidal particles obtained by nano-extrusion in the presence of phospholipids.

Using nano- and microsize extrusion, a simple synthetic procedure of preparing hollow monodispersed colloidal particles dispersed in an aqueous phase was developed. Hydrophobic styrene monomer containing 2-hydroxy-2-methyl propiophenone photoinitiator was forced into desired diameter membrane channels and stabilized by the hydrophobic regions of a liposome obtained from 1,2-dilauroyl-phosphocholine phospholipid in an aqueous phase. Such moieties exposed to 254-nm UV radiation polymerize monomers in the hydrophobic zone of the liposome, thus resulting in reinforced hollow vesicles. The size of such particles is controlled by the size of the membrane channels in the extruder and may vary from a few nanometers to micrometers, thus allowing the synthesis of monodisperse hollow colloidal spheres.

Letter↗
PubMed2000

Synthesis and reactivity of a potential carcinogenic metabolite of tamoxifen: 3,4-dihydroxytamoxifen-o-quinone.

Although tamoxifen is approved for the treatment of hormone-dependent breast cancer as well as for the prevention of breast cancer in high-risk women, several studies in animal models have shown that tamoxifen is heptocarcinogenic, and in humans, tamoxifen has been associated with an increased risk of endometrial cancer. One potential mechanism of tamoxifen carcinogenesis could involve metabolism of tamoxifen to 3,4-dihydroxytamoxifen followed by oxidation to a highly reactive o-quinone which has the potential to alkylate and/or oxidize cellular macromolecules in vivo. In the study presented here, we synthesized the 3,4-dihydroxytamoxifen, prepared its o-quinone chemically and enzymatically, and studied the reactivity of the o-quinone with GSH and deoxynucleosides. The E (trans) and Z (cis) isomers of 3,4-dihydroxytamoxifen were synthesized using a concise synthetic pathway (four steps). This approach is based on the McMurry reaction between the key 4-(2-chloroethoxy)-3,4-methylenedioxybenzophenone and propiophenone, followed by selective removal of the methylenedioxy ring of (E, Z)-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]-1-(3, 4-methylenedioxyphenyl)-2-phenyl-1-butene with BCl(3). Oxidation of 3,4-dihydroxytamoxifen by activated silver oxide or tyrosinase gave 3,4-dihydroxytamoxifen-o-quinone as a mixture of E and Z isomers. The resulting o-quinone has a half-life of approximately 80 min under physiological conditions. Reaction of the o-quinone with GSH gave two di-GSH conjugates and three mono GSH conjugates. Incubation of 3,4-dihydroxytamoxifen with GSH in the presence of microsomal P450 gave the same GSH conjugates which were also detected in incubations with human breast cancer cells (MCF-7). Reaction of 3, 4-dihydroxytamoxifen-o-quinone with deoxynucleosides gave only thymidine and deoxyguanosine adducts; neither deoxyadenosine nor deoxycytosine adducts were detected. Preliminary studies conducted with human breast cancer cell lines showed that 3, 4-dihydroxytamoxifen exhibited cytotoxic potency similar to that of 4-hydroxytamoxifen and tamoxifen in an estrogen receptor negative (ER(-)) cell line (MDA-MB-231); however, in the ER(+) cell line (MCF-7), the catechol metabolite was about half as toxic as the other two compounds. Finally, in the presence of microsomes and GSH, 4-hydroxytamoxifen gave predominantly quinone methide GSH conjugates as reported in the previous paper in this issue [Fan, P. W., et al. (2000) Chem. Res. Toxicol. 13, XX-XX]. However, in the presence of tyrosinase and GSH, 4-hydroxytamoxifen was primarily converted to o-quinone GSH conjugates. These results suggest that the catechol metabolite of tamoxifen has the potential to cause cytotoxicity in vivo through formation of 3,4-dihydroxytamoxifen-o-quinone.

Animals↗
PubMed1994

Fatty acids and other compounds with nematicidal activity from cultures of Basidiomycetes.

In a screening for nematicidal activities in cultures of Basidiomycetes, cultures of Pleurotus pulmonarius and Hericium coralloides exhibited toxic effects towards the saprophytic nematode Caenorhabditis elegans. Subsequently S-coriolic acid (1), linoleic acid (2), p-anisaldehyde (3), p-anisyl alcohol (4), 1-(4-methoxyphenyl)-1,2-propanediol (5), and 2-hydroxy-(4'-methoxy)-propiophenone (6) were isolated from submerged cultures of P. pulmonarius. All compounds showed nematicidal activities towards C. elegans. The most active compounds were 1 and 2 with LD50 values between 5 and 10 ppm. Compounds 1, 4, and 5 have not been previously isolated from higher fungi, 6 is a new natural product. From cultures of H. coralloides, which exhibited both repellant and nematicidal effects, a nematicidal fatty acid mixture was obtained, containing linoleic acid, oleic acid, and palmitic acid as its main components.

Animals↗
PubMed2001

High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities.

A reversed-phase high-performance liquid chromatographic procedure for the simultaneous determination of impurities associated with pseudoephedrine hydrochloride (PSEH) and naproxen sodium (NapNa) is developed and validated. The method is developed using a Waters Spherisorb cyano column (5 microm, 250 x 4.6 mm). An isocratic elution in a water-acetonitrile-methanol-triethylamine mixture (850:75:75:5) is adjusted to a pH of 3.7 +/- 0.02 with formic acid as the mobile phase. The UV detection was set at 260 nm, and the wavelength was switched to 235 nm before the elution of the last component, 2-ethyl-6-methoxy-naphthalene (EMN). The method is shown to be linear at a concentration range of 0.24 to 1.92 microg/mL for benzaldehyde, benzoic acid, and 2-(methylamino)-propiophenone hydrochloride, which are known impurities of PSEH. The NapNa impurities, 2-(6'-hydroxy-2'-naphthyl) propionic acid, 2-hydroxy-6-methoxy-naphthalene, 1-(6'-methoxy-2'-naphthyl) ethanol, 2-acetyl-6-methoxy-naphthalene, and EMN are also demonstrated to be linear at a concentration range of 0.44 to 3.52 microg/mL. Under the chromatographic conditions of the method, all impurities are resolved from the active components.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed2004

Preliminary study on rapid identification of Mycobacterium tuberculosis complex isolates by the BD ProbeTec ET system.

The BD ProbeTec ET system for identification of Mycobacterium tuberculosis complex (MTBC) isolates from BACTEC 12B culture vials was evaluated in comparison with BACTEC NAP (p-nitro-alpha-acetylamino-beta-hydroxy-propiophenone) differentiation. Of 145 mycobacterial isolates tested, comprising 89 MTBC and 56 non-tuberculous mycobacteria (NTM), BD ProbeTec ET correctly identified 87 MTBC and 56 NTM but missed two MTBC. Three NTM were misidentified when NAP was incubated at 37 degrees C only. Overall sensitivity, specificity and positive and negative predictive values were respectively 97.8, 100, 100 and 96.6 % for the BD ProbeTec ET system and 100, 94.6, 96.7 and 94.6 % for NAP.

Bacteriological Techniques↗
PubMed2003

(E,E)-1,4-Diethyl-1,4-diphenyl-2,3-diazabutadiene.

Molecules of the title compound [(E,E)-propiophenone azine], C(18)H(20)N(2), lie across centres of inversion in space group P2(1)/c. The conformations of similar simple azines are discussed in terms of the soft hydrogen bonds present in the structures.

Journal Article↗
PubMed1991

Accumulation and release of adrenaline, and the modulation by adrenaline of noradrenaline release from rabbit blood vessels in vitro.

The accumulation of (-)-3H-adrenaline (3H-A) by rabbit isolated aorta was studied. In all experiments, monoamine oxidase and catechol-O-methyltransferase were inhibited by treatment with pargyline and 3',4'-dihydroxy-2-methyl-propiophenone, respectively. The relationship between the accumulation of 3H derived from 3H-A and the duration of incubation was linear. The 3H-accumulation after 3 h incubation was 22.5 ml/g. In reserpine-treated tissue, the 3H-accumulation levelled off after 30 min and was 8.5 ml/g after 3 h. The concentration of 3H-A or (-)-3H-noradrenaline (3H-NA) and the 3H-accumulation (ml/g) were inversely related. At 10(-8) M, the 1-hour accumulation of 3H derived from 3H-A and 3H-NA was 7.8 and 15.2 ml/g, respectively. With increasing concentrations the accumulation values approached each other. The accumulation of 3H derived from 3H-A by reserpine-treated tissue also showed an inverse relationship with concentration. The accumulation of 3H derived from 3H-A was dependent on the bath temperature. Storage of tissue (0-5 days in salt solution without equilibration with 95% O2/5% CO2; 4 degrees C) did not affect the accumulation of 3H derived from 3H-A. Thereafter (7-14 days), the accumulation decreased. The inhibitory potency (IC50; -log M) of desipramine, cocaine, propranolol, isoprenaline, and normetanephrine on accumulation of 3H derived from 3H-A was found to be 8.26; 6.50; 5.48; 4.88, and 4.02, respectively. The maximal degree of inhibition was almost the same for these drugs, while that of clonidine and corticosterone was 50 and 20%, respectively. In the presence of desipramine, either clonidine, corticosterone or isoprenaline reduces the accumulation of 3H derived from 3H-A. Ouabain and iodoacetic acid, but not sodium cyanide and 2,4-dinitrophenol, reduced the accumulation of 3H derived from 3H-A. Anoxia (95% N2/5% CO2; 37 degrees C; 1-24 h) did not alter the accumulation of 3H derived from 3H-A. Glucose deprivation alone or combined with anoxia markedly reduced the 3H-accumulation. The release of 3H-A from rabbit isolated aorta was studied. This release was compared with that of 3H-NA. The stimulation-evoked 3H-overflow from aorta preloaded with 3H-A decreased with repeated stimulation. In contrast, prestimulation enhanced subsequent stimulation-evoked 3H-overflows. For both 3H-amines, the 3H-overflow increased concomitantly to the same degree with the number of pulses. The time course of 3H-overflows with either 3H-A or 3H-NA was compared.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗
PubMed1978

The indirect sympathomimetic activity of etilefrine--a comparison with tyramine and ephedrine using [3H] noradrenaline.

The indirect sympathomimetic activity of etilefrine has been examined using the ventral caudal artery of the rat. This vessel has a rich sympathetic innervation and lends itself to studies on [3H]noradrenaline efflux from these sites. Etilefrine possessed significant indirect activity on the artery and this action, although less than that of tyramine, was equivalent to that caused by ephedrine. Pretreatment of the vessels with a mixture of iproniazid, doca, cocaine and UO521 (3',4'-dihydroxy-2-methyl propiophenone) significantly enhanced[3H]-noradrenaline efflux from the artery.

Animals↗
PubMed1981

Uptake and metabolism of noradrenaline by blood vessels of perinephritic hypertensive dogs.

Tissue noradrenaline content as well as uptake and metabolism of tritiated exogenous noradrenaline were studied comparatively, in vitro in mesenteric arteries, and in saphenous veins of normotensive and perinephritic hypertensive dogs. The influence of cocaine, iproniazid and 3'-4'-dihydroxy-2-methyl-propiophenone (U-0521) on these variables was also investigated. The concentration of (-)-7-3H-noradrenaline used was 1.08 microM. No changes were observed in noradrenaline content, uptake and metabolism in saphenous vein strips obtained from normotensive or hypertensive animals. However, in mesenteric artery strips obtained from hypertensive dogs, a marked reduction in endogenous noradrenaline content was observed as well as a reduction in noradrenaline accumulation (20 weeks after surgery). The deamination pattern was also modified in these strips: the formation of DOPEG was markedly diminished and the formation of DOMA was increased. These results agree well with the degeneration of the sympathetic innervation of the mesenteric arteries of hypertensive dogs described by Azevedo et al. (1981).

Animals↗
PubMed1984

Rapid radiometric methods to detect and differentiate Mycobacterium tuberculosis/M. bovis from other mycobacterial species.

Rapid methods for the differentiation of Mycobacterium tuberculosis/M. bovis (TB complex) from other mycobacteria (MOTT bacilli) were developed and evaluated in a three-phase study. In the first phase, techniques for identification of Mycobacterium species were developed by using radiometric technology and BACTEC Middlebrook 7H12 liquid medium. Based on 14CO2 evolution, characteristic growth patterns were established for 13 commonly encountered mycobacterial species. Mycobacteria belonging to the TB complex were differentiated from other mycobacteria by cellular morphology and rate of 14CO2 evolution. For further differentiation, radiometric tests for niacin production and inhibition by Q-nitro-alpha-acetyl amino-beta-hydroxy-propiophenone (NAP) were developed. In the second phase, 100 coded specimens on Lowenstein-Jensen medium were identified as members of the TB complex, MOTT bacilli, bacteria other than mycobacteria, or "no viable organisms" within 3 to 12 (average 6.4) days of receipt from the Centers for Disease Control. Isolation and identification of mycobacteria from 20 simulated sputum specimens were carried out in phase III. Out of 20 sputum specimens, 16 contained culturable mycobacteria, and all of the positives were detected by the BACTEC method in an average of 7.3 days. The positive mycobacterial cultures were isolated and identified as TB complex or MOTT bacilli in an average of 12.8 days. The radiometric NAP test was found to be highly sensitive and specific for a rapid identification of TB complex, whereas the radiometric niacin test was found to have some inherent problems. Radiometric BACTEC and conventional methodologies were in complete agreement in Phase II as well as in Phase III.

Cells, Cultured↗
PubMed1992

Purines. LII. Synthesis and biological evaluation of 8-methylguanine 7-oxide and its 9-arylmethyl derivatives.

The synthesis of 8-methylguanine 7-oxide (3) was accomplished via a "phenacylamine route", which started from condensation of alpha-(4-methoxybenzylamino)propiophenone (6), prepared by coupling of alpha-bromopropiophenone (4) and 4-methoxybenzylamine (5), with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone (7) and proceeded through cyclization of the resulting phenacylaminopyrimidinone (8) and removal of the 4-methoxybenzyl group. The N-oxide 3 and its 9-arylmethyl derivatives 9 and 11 showed only very weak antileukemic activity and no antimicrobial activity.

Animals↗
PubMed1999

Optically active antifungal azoles. IX. An alternative synthetic route for 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4- triazol-1-yl)propyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]- 3(2H,4H)-1,2,4-triazolone and its analogs.

A new route for the synthesis of the optically active antifungal azole TAK-187, 2-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-tria zol-1- yl)propyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4 - triazolone, was established. The key synthetic intermediate, 2-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-4-[4-(2,2,3,3- tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (8), was prepared starting from the esters (11a, b) of (S)-lactic acid in a stereocontrolled manner. This optically active propiophenone derivative 8 was converted to the one carbon-elongated (1R,2S)-diol 7, which was then reacted with 1H-1,2,4-triazole to yield TAK-187. This newly developed route was applied to the synthesis of the analogs (25a, b--28a, b) containing an imidazolone or imidazolidinone nucleus.

Antifungal Agents↗
PubMed2005

Metabolism of designer drugs of abuse.

Abuse of designer drugs is widespread among young people, especially in the so-called "dance club scene" or "rave scene", worldwide. Severe and even fatal poisonings have been attributed to the consumption of such drugs of abuse. However, in contrast to new medicaments, which are extensively studied in controlled clinical studies concerning metabolism, including cytochrome P450 isoenzyme differentiation, and further pharmacokinetics, designer drugs are consumed without any safety testing. This paper reviews the metabolism of new designer drugs of abuse that have emerged on the black market during the last years. Para-methoxyamphetamine (PMA), para-methoxymethamphetamine (PMMA) and 4-methylthioamphetamine (4-MTA), were taken into consideration as new "classical" amphetamine-derived designer drugs. Furthermore, N-benzylpiperazine (BZP), 1-(3, 4-methylenedioxybenzyl)piperazine (MDBP), 1-(3-trifluoromethylphenyl)piperazine (TFMPP), 1-(3-chlorophenyl)piperazine (mCPP) and 1-(4-methoxyphenyl)piperazine (MeOPP) were taken into consideration as derivatives of the class of piperazine-derived designer drugs, as well as alpha-pyr-rolidinopropiophenone (PPP), 4'-methoxy-alpha-pyrrolidinopropiophenone (MOPPP), 3', 4'-methylenedioxy-alpha-pyrrolidino-propiophenone (MDPPP), 4'-methyl-alpha-pyrrolidinopropiophenone (MPPP), and 4'-methyl-alpha-pyrrolidinoexanophenone (MPHP) as derivatives of the class of alpha-pyrrolidinophenone-derived designer drugs. Papers describing identification of in vivo or in vitro human or animal metabolites and cytochrome P450 isoenzyme dependent metabolism have been considered and summarized.

Animals↗