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  • 1
    Electronic Resource
    Electronic Resource
    Racemisation of drug enantiomers by benzylic proton abstraction at physiological pH (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 400-404 
    Details
    ISSN: 0899-0042
    Keywords: econazole ; 3-(4-aminophenyl)pyrrolidine-2,5-diones ; aromatase inhibitors ; antifungals ; drug registration ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomers of the aromatase inhibitors 3-(4-aminophenyl)-pyrrolidine-2,5-dione (WSP-3, II), its N-pentyl derivative (III), and the antifungal econazole (IV), all possessing a benzylic proton at the chiral centre, are rapidly racemised in vitro in phosphate buffer (0.01 M) at pH 7.4 and 23°C with t½ values of 7, 6, and 5 h respectively. In vivo studies in rats show that (+)-econazole is racemised after intraperitoneal injection with t½ = 1.24h. The enantiomers of the antifungal 1-[(benzofuran-2-yl)-4-chlorophenylmethyl] imidazole (V) were stable at pH 7.4, attributable to steric hindrance to carbanion formation in the racemisation step. © 1994 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060507
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  • 2
    Electronic Resource
    Electronic Resource
    Enantioselectivity of aromatase inhibitors: Substituted 3-(4-aminophenyl)pyrrolidine-2,5-diones (1995)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 7 (1995), S. 376-380 
    Details
    ISSN: 0899-0042
    Keywords: aromatase ; P450AROM ; cholesterol side chain cleavage enzyme ; P450CSCC ; spectral binding studies ; inhibition ; substituted 3-(4-aminophenyl)pyrrolidine-2,5-diones ; aminoglutethimide ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The (+)-, (-)-, and (±)-forms of 1- and 1,3-substituted 3-(4-aminophenyl)pyrrolidine-2,5-dione have been examined as inhibitors of P450AROM and P450CSCC. The inhibitory potency for P450AROM resided in the (+)-enantiomers of (1), (2), and (4) and the (-)-enantiomers of (3) and (5). These findings have been accommodated within a molecular graphics-derived model for binding of P450AROM inhibitors to the substrate binding site. Crystallography showed that (+)-(2) has the (R)-configuration. Spectral binding studies with human placental P450AROM showed type II binding but although the KS values were in line with the IC50 values for individual compounds there was no overall correlation between KS and IC50 within the series. There was little difference in the inhibitory potency of the enantiomers and racemate of individual compounds toward P450CSCC. © 1995 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530070511
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    Paper (German National Licenses)
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