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  • Organic Chemistry  (41)
  • Wiley-Blackwell  (41)
  • American Institute of Physics
  • International Union of Crystallography (IUCr)
  • 1995-1999  (23)
  • 1975-1979  (9)
  • 1970-1974  (9)
  • 1
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 320 (1978), S. 1029-1035 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Spektrophotometrische Untersuchungen einiger Arylidenderivate von Benzoe- und Salicylsäurehydraziden in Pufferlösungen
    Additional Material: 2 Ill.
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  • 2
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 321 (1979), S. 899-904 
    ISSN: 0021-8383
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaktionen von Acetylenestern mit cyclischen Ketonen und substituierten AcetophenonenDie Kondensation von substituierten Phenylpropiolsäureestern mit cyclischen Ketonen führt zu polycyclischen Pyronen. Die Kombination spektroskopischer Methoden zeigt, daß Cyclopentanon zu 4-Pyronen (I), Cyclohexanon, Cycloheptanon, Cyclooctanon dagegen zu 2-Pyronen (IIa-f) reagiert.Die Kondensation von Ethylarylpropiolaten mit p-Piperazino, p-Piperidino, p(4-Methylpiperazino) und p-Morpholinoacetophenonen ergibt die p-(4-Arylpropiolylpiperazino) acetophenone (IIIa-d), 2-(p-Piperidinophenyl)-6-aryl-4-pyrone (IVa-c), 2-(p-4-Methylpiperazino-phenyl)-6-aryl-4-pyrone (Va-c) und 2-(p-Morpholinophenyl)-6-aryl-4-pyrone (VIa - d). Die Acetylen-β-diketone (VII) erhält man aus Ethyl-p-tolylpropiolat mit p-Piperidinoacetophenon.
    Additional Material: 2 Tab.
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  • 3
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Applied Organometallic Chemistry 9 (1995), S. 365-365 
    ISSN: 0268-2605
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
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  • 4
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On ultraviolet irradiation of the cyclopent-2-enyl methyl ketones 1a-c at -54° ≤ t ≤ 139°, photo-CIDNP. effects of the starting ketones, the 1,3-acetyl shifted isomers (2), and radical disproportionation and combination products (4-7) were observed. These effects show a unique dependence of the polarization phase on temperature which is a novel feature in photo-CIDNP. studies. The results of the investigation, which also included experiments using triplet quenchers, triplet sensitizers and radical scavengers, are rationalized in terms of Schemes 2 and 3.α-Cleavage is a major excited-state reaction of 1a-c on direct irradiation. Temperature-activated α-cleavage (kaS(t)) to the radical pair R · · R′1 and intersystem crossing (kisc) to the T2 state are among the competing S1 deactivation processes. The T2 state in turn cleaves (kaT2) to R · · R′3 A ‘low-temperature range’ with kisc ≫ kaS(t) and a ‘high-temperature range’ with kaS(t) ≫ kisc exhibiting preferential reactivity from the T2 and S1 states, respectively, can be defined for all three β,γ-unsaturated ketones 1a-c.
    Additional Material: 3 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 80 (1997), S. 695-705 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Syntheses of cyclosporine analogues are reported wherein the peptide couplings were achieved in solid phase. The Wang resin was used as the solid support, and the peptide couplings commenced with the residue 11 of the cyclosporine skeleton. The couplings proceeded in a stepwide manner up to the residue MeBmt1, using symmetric anhydrides. The peptides were then cleaved off the resin, and the cyclization was achieved in solution using Castro's reagent. The solid-phase synthesis described herein offers a very efficient method for the rapid synthesis of structurally diverse cyclosporine analogues in small quantities. The biological activities of the synthetic cyclosporine analogues were evaluated in two in vitro assays, including the IL-2 reporter gene assay and the cyclophilin binding assay. The structure-activity relationship is discussed.
    Additional Material: 2 Tab.
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  • 6
    ISSN: 0899-0042
    Keywords: Chiralcel OD column ; direct reaction monitoring ; β-blocker intermediate ; Amano lipase AK ; enantiomeric excess ; timolol ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomeric purities of both substrate, 2-acetoxy-3-bromopropyl para-toluenesulfonate (I), and product, 2-hydroxy-3-bromopropyl p-toluenesulfonate (II) were examined in one analysis. The enzymatic resolution was conducted by Amano lipase AK and the enantiomeric excess as well as the conversion rate were monitored by HPLC analysis utilizing a Chiralcel OD column. After 7 h of reaction, HPLC results indicated that the enantiomeric purities of both substrate (I) and product (II) were greater than 95% and the conversion rate was around 55%. © 1995 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
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  • 7
    ISSN: 0899-0042
    Keywords: supercritical fluid chromatography ; profens ; 2-arylpropionic acids ; barbiturates ; benzodiazepines ; tris(4-methylbenzoate) cellulose ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Supercritical fluid chromatography was applied to evaluate the direct chiral discriminative properties of Chiralcel OJ, a tris(4-methylbenzoate) cellulose column towards frequently administered drugs. Two groups of acidic drugs, profen and barbiturate derivatives, and a few basic drugs of the benzodiazepine type were analysed. The effect on enantioselectivity of carbon dioxide when using methanol are acetonitrile as primary modifier was studied. Acetonitrile proved to be a good alternative for methanol, especially for the profen compounds that were not well resolved using methanol. The results were compared to normal phase chromatographic applications on the same column. SFC was not necessarily superior to high-performance liquid chromatography. Chirality 9:126-132, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 4 Ill.
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  • 8
    ISSN: 0899-0042
    Keywords: propranolol enantiomers ; fluorinated analogs ; chiralcel OD and chiralcel OD-R columns ; chiral recognition mechanism(s) ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomeric separation of several racemic aryloxyaminopropan-2-ol derivatives related to propranolol on normal and reversed phase of cellulose tris (3,5-dimethylphenylcarbamate) chiral stationary phases known as Chiralcel OD and Chiralcel OD-R were studied. It was observed that the chiral separation depends on the substitution pattern of the aryl group, i.e., 1-naphthyl, 2-naphthyl, and phenyl group and polarity on the basic nitrogen in the side chain. In both normal and reversed phase modes the (+)-R-enantiomer eluted first in all of the analogs resolved. It can be concluded that: (1) substituents on the side chain did affect the interaction of the enantiomers with the polar carbamate moiety in the CSP; and (2) the dipole-dipole stacking between the π-donor 3,5-dimethylphenyl carbamate group pending from the glucose rings of the CSP and π-acceptor aryl group of the analyte is crucial for the efficient chiral discrimination. The chiral recognition mechanism(s) between these analogs and the chiral stationary phases are proposed. © 1996 Wiley-Liss, Inc.
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  • 9
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 528-534 
    ISSN: 0899-0042
    Keywords: chiral inversion ; ibuprofen ; ketoprofen ; flurbiprofen ; indoprofen ; suprofen ; fenoprofen ; metabolism of 2-arylpropionic acids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The fungus Cordyceps militaris has been previously shown to be capable of inverting the chirality of 2-phenylpropionic acid from its (R)-enantiomer to its (S)-antipode. The structure of this compound is similar to the 2-arylpropionic acid non-steroidal anti-inflammatory drugs, which have also been reported to undergo a similar chiral inversion process in mammals and man. We report here an investigation into the substrate specificity of the enzyme system present in C. militaris using pure enantiomers and racemates of ibuprofen and ketoprofen and racemates of indoprofen, suprofen, flurbiprofen, and fenoprofen and the structurally related compounds 2-phenylbutyric acid and 2-phenoxypropionic acid as substrates, using optimised incubation conditions developed for the inversion of 2-phenylpropionic acid. The results demonstrated that C. militaris is capable of inverting the chirality of all the compounds investigated, which suggests that the active sites of the enzymes are very flexible with regard to the molecular dimensions of the substrate molecule and the spatial occupation of the groups surrounding the chiral centre. Metabolism of all the substrates was observed but the rate of metabolism varied extensively depending on the substrate. Achiral HPLC analysis was used to detect any potential metabolites and the results suggested that the site of the metabolism appeared to be at the aliphatic side groups only, with the aromatic ring being left intact in all cases. These results suggest that C. militaris could be a valuable tool in the investigation of the prospective metabolic fates of new 2-arylpropionic acids during their development. Chirality 10:528-534, 1998. © 1998 Wiley-Liss, Inc.
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  • 10
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 10-12 
    ISSN: 0899-0042
    Keywords: piperidine-2,6-dione ; chiral recognition ; enantioselectivity ; elution order ; cellulose based chiral stationary phase ; reversed phase mode ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A newly developed reversed phase cellulose tris(4-methyl benzoate) known as Chiralcel OJ-R was used to investigate the chiral recognition and enantiomeric separation of eight racemic piperidine-2,6-dione compounds - namely, aminoglutethimide and its major metabolite acetylaminoglutethimide, glutethimide, cyclohexylamino-glutethimide, pyridoglutethimide, thalidomide, phenglutarimide, and 3-phenylacetyl-amino-2,6-piperidinedione (antineoplaston A-10). Chiral separation of these compounds was achieved under varying ratios of the mobile phase, except for phenglutarimide and 3-phenylacetylamino-2,6-piperidinedione, for which separation was unsuccessful. Possible chiral recognition mechanisms are also presented. Chirality 9:10-12, 1997. © 1997 Wiley-Liss, Inc.
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