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  • 1
    Electronic Resource
    Electronic Resource
    Ozonide von isomeren Octalinen durch trockene Ozonolyse auf Polyethylen (1996)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 338 (1996), S. 179-181 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ozonides of Isomeric Octalins by Dry Ozonolysis on Polyethylene
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19963380135
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  • 2
    Electronic Resource
    Electronic Resource
    On the reaction of (S)-trifluoroacetoxysuccinic anhydride with amines to produce hydroxysuccinamic (malamic) acid derivatives (1998)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 340 (1998), S. 733-737 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: L-Malic acid (2) reacts with trifluoroacetic anhydride under anhydrous conditions to give (S)-trifluoroacetoxy-succinic acid anhydride (3). The anhydride 3 undergoes regioselective ring opening with an excess of anilines or primary aliphatic amines leading to N-substituted-(S)-3-hydroxy-succinamic acids (4a-g). Structural elucidation of the reaction products 4a-g was based on analytical and spectroscopic data and on an X-ray structure analysis of 4b. Secondary aliphatic amines react with 3 by condensation and subsequent elimination to furnish N,N′-disubstituted fumaric acid amides 5a, b. Some N-substituted-2-hydroxysuccinamic acids (7a,b) were also prepared for spectral comparison with the 3-hydroxy compounds.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19983400805
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  • 3
    Electronic Resource
    Electronic Resource
    cis/trans-ozonides of cycloolefins (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1993-1999 
    Details
    ISSN: 0947-3440
    Keywords: Ozonides ; Cycloolefins ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ozonolyses in pentane of the unsubstituted cycloolefins having eleven-, twelve-, fourteen- and sixteen-membered rings (1b-e) and of cyclohexadecen-8-one (12) gave the corresponding cis- (2b-e; cis-15a) and trans-ozonides (3b-e; trans-15a), whereas cyclodecene (1a) gave only the corresponding cis-ozonide (2a). Ozonolyses on polyethylene of the dimethyl-substituted cycloolefins bearing fourteen- and sixteen-membered rings (7b, c) also afforded cis- and trans-isomeric ozonides (8, 9), whereas from the twelve-membered ring (7a) only the corresponding cis-ozonide (8a) was formed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199511279
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  • 4
    Electronic Resource
    Electronic Resource
    Anodic Oxidation of Norcamphor in Aqueous Electrolytes (1992)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 334 (1992), S. 37-40 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Norcamphor (1) was anodically oxidized at Pb/PbO2 anodes in 1 M · H2SO4, MeCN/H2O (V/V = 1/1). 3-Oxocyclopentaneacetic acid (3) and oxabicyclo[3.3.0]octan-3-one (4) were obtained with material yields up to 76% and 42%, respectively. The effects of electrode materials, current densities and concentrations were studied. A possible anodic oxidation mechanism was proposed.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19923340107
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  • 5
    Electronic Resource
    Electronic Resource
    New 2,5-dihydroimidazole-1-oxyls with functional side groups (N, O, S donors) (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 2189-2194 
    Details
    ISSN: 0947-3440
    Keywords: Nitroxide radicals ; 2,5-Dihydroimidazoles ; Hydroxylamines, secondary ; α-Keto hydroxylamines ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of functionalized 2,5-dihydro-1-hydroxy-2-R1-2-R2-4-R3-imidazoles were prepared by cyclocondensation of α-oxo hydroxylamines with ketones R1R2C = O in the presence of ammonia (R1 = R2 = 2-pyridyl, 4,5-diazafluoren-9-ylene, R3 = Me; R1 = CH2OCOMe, CH2OCOPh, 2-thienyl, CH2OH, CO2K, R2 = R3 = Me; R1 = Py, R2 = Me, R3 = Ph; R1 = R2 = CH2OCOPh, CH2OH, R3 = Me) and oxidized to the corresponding nitroxide radicals. The structures of 2′,5′-dihydro-1′-hydroxy-4′,5′,5′-trimethylspiro[4,5-diazafluoren-9,2′-imidazole] (2) and of 2-(acetoxymethyl)-2,5-dihydro-2,4,5,5-tetramethylimidazole-1-oxyl (14) were determined by X-ray diffraction. In the crystal 2 forms one-dimensional chains through hydrogen bonding between N atoms of the hydroxylamine and imidazoline groups.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199512304
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  • 6
    Electronic Resource
    Electronic Resource
    Lambda-carrageenan: A novel chiral selector for capillary electrophoresis (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 503-510 
    Details
    ISSN: 0899-0042
    Keywords: enantioseparations ; carrageenans ; sulfated polysaccharides ; beta blockers ; tryptophan and derivatives ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Lambda-carrageenan, a linear high molecular weight sulfated polysaccharide, has been employed as a chiral selector in capillary electrophoresis for the separation of enantiomers of weakly basic pharmaceutical compounds. The racemic compounds that were enantioresolved included propranolol, pindolol, tryptophanol, laudanosine and laudanosoline. In addition, the diastereomeric pair of cinchonine and cinchonidine were also resolved. Method conditions such as buffer pH, electrolyte concentration, column temperature, and chiral selector concentration were found to be important for improvement of enantioselectivity. © 1996 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Pharmacokinetics of ibuprofen enantiomers in dogs (1991)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 3 (1991), S. 165-169 
    Details
    ISSN: 0899-0042
    Keywords: ibuprofen ; enantiomer ; stereoselectivity ; chiral inversion ; pharmacokinetics ; dog ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Inversion of inactive (R)-ibuprofen to active (S)-ibuprofen has been suggested to occur presystemically only. In order to investigate the site of inversion in dogs we administered both enantiomers either intravenously or intraduodenally (10 mg/kg) to adult, male beagle dogs (n = 3) in a crossover design. Plasma, urine, and bile were collected for up to 6 h and analyzed stereospecifically by HPLC, according to a previously published method. Pharmacokinetic parameters were calculated using a linear computer program. Absorption after intraduodenal administration occurred rapidly, resulting in maximum plasma concentrations 0.2 h after giving the enantiomer. Approximately 70% of the (R)-enantiomer (according to AUC) was inverted to the S-enantiomer independent of route of administration. No R-ibuprofen could be detected in plasma after (S)-ibuprofen administration. Mean residence time was found to be 2 to 3 times longer for (S)-than for (R)-ibuprofen. Total systemic clearance from plasma was twice as high for (R)- than for (S)-ibuprofen. There were no differences between plasma clearances after intravenous and intraduodenal administration. Between 8 and 17% of dose was recovered in bile [especially as free and conjugated (S)-ibuprofen] and 3-12% in urine [as (S)-ibuprofen, hydroxy- and carboxyibuprofen, free and conjugated forms]. Small amounts of (R)-ibuprofen were detected in bile after intraduodenal administration of (R)-ibuprofen only (1.8% of dose). In short, the unidirectional inversion of R-ibuprofen appears to occur systemically rather than presystemically in dogs.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530030304
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  • 8
    Electronic Resource
    Electronic Resource
    Mechanistic aspects of the biogenesis of rose oxide in Pelargonium graveolens L'Héritier (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 229-237 
    Details
    ISSN: 0899-0042
    Keywords: deuterium labelling ; menthocitronellol ; citronellol ; enantioselective multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS) ; dynamic headspace analysis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mechanistic aspects of the biogenesis of the chiral monoterpenoid rose oxide in Pelargonium graveolens L'Héritier are investigated using deuterium-labelled precursors. After administration of the precursors using the cut-stem method, the dynamic headspace extracts of the plants are analysed using multidimensional gas chromatography-mass spectrometry (enantio-MDGC-MS). It is unequivocally shown that this plant is able to convert citronellol and menthocitronellol into cis-/trans-rose oxide. Menthocitronellol is converted into rose oxide with a clearly detectable enantiodiscrimination. These facts may be explained with the presence of an oxidase, which is able to oxidize citronellol and menthocitronellol in allylic position. A photooxygenation mechanism including singlet oxygen as the oxidizing agent is rather unlikely. Chirality 10:229-237, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 9
    Electronic Resource
    Electronic Resource
    Stereoselectivity of biliary excretion of 2-arylpropionates in rats (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 422-427 
    Details
    ISSN: 0899-0042
    Keywords: 2-arylpropionates ; enantiomers ; stereoselectivity ; chiral inversion ; pharmacokinetics ; bile-duct cannulated rats ; biliary excretion ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: To examine the stereoselectivity of biliary excretion, the optically pure enantiomers of ketoprofen (KT), ibuprofen (IBU), and flurbiprofen (FLU) were intravenously administered to normal and bile duct-cannulated rats at 10 mg/kg. The recovery of total KT in bile was significantly higher after administration of (S)-KT than after (R)-KT [90.1 ± 3.5% vs 68.8 ± 8.2%, n =3, P 〈 0.05]. In normal rats the terminal half-life of (R)-KT was significantly shorter than that of (S)-KT after administration of (R)-KT (2.2 ± 0.6 h vs 14.3 ± 4.9 h, n = 3, P 〈 0.05). The terminal half-life of both enantiomers was significantly shorter in rats with continuous bile drainage as compared to normal rats. No significant differences in pharmacokinetic parameters could be found between both enantiomers in bile duct-cannulated animals. The total amount of IBU in bile was slightly higher after administration of (S)-IBU than after (R)-IBU administration. The percentage of (R)-IBU after (R)-IBU administration, however, was very low [(R)-IBU: 1.5 ± 0.9%, (S)-IBU: 23.4 ± 5.8%]. In normal rats the clearance of (R)-IBU was significantly higher as compared to (S)-IBU. Differences in pharmacokinetic parameters between normal and bile duct-cannulated rats were not statistically significant due to high interindividual variability. The total recovery of FLU, which was excreted in bile to a lower extent than either KT or IBU, also tended to be greater after S-enantiomer administration. Only small amounts of (S)-FLU could be recovered in bile after (R)-FLU administration. The pharmacokinetic parameters did not differ significantly between (R)- and (S)-FLU or between normal and bile duct-cannulated rats due to its low inversion rate and low excretion via bile. © 1993 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530050606
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  • 10
    Electronic Resource
    Electronic Resource
    Revised Structure of the Fungal Germination Self-Inhibitor Gloeosporone (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 281-291 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Gloeosporone, the germination self-inhibitor from the fungus Colletotrichum gloeosporioides f.sp. jussiaea, is shown by spectroscopic data and X-ray analysis to have the constitution and relative configuration as shown in Formula 2 (either (1S,6R,12R)-1-hydroxy-6-pentyl-5,15-dioxabicyclo[10.2.1]pentadecan-4,13-dione or its enantiomer), rather than the previously assigned constitution 1.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700203
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