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  • 1
    ISSN: 0899-0042
    Keywords: receptor-operated calcium channel antagonist ; 1H NMR ; chiral HPLC ; calmodulin ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1H nuclear magnetic resonance at 360 MHz shows that SK&F 96365 (1-{β-[3-(p-methoxyphenyl)-propyloxy]-p-methoxyphenethyl}-1H- imidazole hydrochloride), an antagonist of mammalian receptor-operated calcium channels, interacts with the calcium-binding regulatory protein calmodulin (CaM). This may be inferred by a number of chemical shift changes in the spectrum of the calcium-saturated protein induced by addition of the compound. Moreover, two well-resolved singlets corresponding to the 2-proton of the SK&F 96365 imidazolium moiety are observed in the spectrum over a wide range of protein:compound ratios. Separation of rac SK&F 96365 into its two enantiomers by high-performance liquid chromatography on a cellulose tris (4-methylbenzoate) column enabled us to show that the doubling of this NMR signal in the presence of CaM is due to a propensity of the protein to distinguish between the two optical isomers of the compound.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 239-244 
    ISSN: 0899-0042
    Keywords: HPLC ; reverse-phase additive ; β-cyclodextrin ; methylphenobarbitone ; molecular mechanics ; complex stability ; chiral separation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Molecular modelling of β-cyclodextrin and optimisation of its potential energy suggests that a favoured conformation is that distorted from a symmetrical torus. The inclusion of water molecules into the torus cavity simulates the increased stability in an aqueous solvent. Complexes of β-cyclodextrin with (R)- and (S)-enantiomers of methylphenobarbitone have been modelled and energetically optimised by the application of molecular mechanics. The simulations suggests that the guest molecules adopt an orientation in which the phenyl ring is projected into the torus cavity, with in each case the plane of the ring parallel to a longer axis of the distorted torus and slightly displaced from the axis through the torus cavity. It is suggested that the asymmetry in the macrocyclic ring contributes to chiral recognition as a result of additional discriminatory binding to the barbiturate ring residue of each enantiomer, which occupy different 3D geometries. The enantiomers form complexes of different minimum potential energies. The resulting difference in complex stability can be related to the behaviour of β-cyclodextrin, as a mobile phase additive in reverse-phase HPLC to effect chiral separation of rac-medthylphenobarbitone during chromatography. © 1994 Wiley-Liss, Inc.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 58-66 
    ISSN: 0899-0042
    Keywords: molecular mechanics ; HPLC ; chiral separation ; methylphenobarbitone ; hexobarbitone ; ibuprofen ; mandelic acid ; ephedrine ; pseudoephedrine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: β-Cyclodextrin and its derivatives have been utilised to effect chiral separation in HPLC and CZE, both as stationary phases and mobile phase additives. The basis of the method is assumed to depend upon the formation of inclusion complexes of differing stabilities between enantiomeric analytes and the cyclodextrin, resulting in a differential dynamic distribution between chromatographic phases. In this study, force field calculations have been employed to model the inclusion complexes of enantiomeric brompheniramine, ephedrine, pseudoephedrine, ibuprofen, mandelic acid, methylphenobarbitone, and hexobarbitone with β-cyclodextrin. The resulting values for Δ(ΔH), the difference in enthalpy of complex formation between enantiomeric pairs has been compared with literature chromatographic data to explain the ability of the systems to achieve enantiomeric separations. © 1996 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 613 (1958), S. 56-60 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Aus Dihydro-robinetin (X) entsteht durch Hydrierung das kristalline Leukorobinetinidin-hydrat (VI). Es läßt sich in das zugehörige Anthocyanidin, das Robinetinidin, verwandeln, das zum Vergleich synthetisiert wurde.  -  Im Quebrachoholz wurde ein ( - )-Leuko-fisetinidin-hydrat (VII) gefunden. Es ist einer der Stammkörper des Quebrachogerbstoffs und mit dem Bestandteil gleicher Konstitution der Acacia mollissima (Mollisacacidin von H. H. KEPPLER) stereomer.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Chichester : Wiley-Blackwell
    Journal of Physical Organic Chemistry 7 (1994), S. 705-711 
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: An infrared spectroscopic study of the 1 : 1 hydrogen-bond association of amidates with both methanol and 4-fluorophenol showed that the site of complexation is the oxygen of the amidate function. However the formamidate HCON2Me3 forms a second 1 : 1 complex on the nitrogen of the amidate. The formation constants of the hydrogen-bond complexes of the amidates with the reference hydrogen-bond donor 4-FC6H4OH indicate that the amidates are stronger hydrogen-bond bases than are amides and amide vinylogues. As such, the amidates constitute the strongest carbonyl bases hitherto investigated on the hydrogen-bond basicity scale.
    Additional Material: 5 Ill.
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  • 6
    ISSN: 0894-3230
    Keywords: Organic Chemistry ; Physical Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: An IR spectroscopic study of the hydrogen bonding of Bu3N+N-C≡N with 4-fluorophenol showed that the site of complexation is the nitrogen of the nitrile function. THe formation constant of the 1:1 complex in CCl4 indicates that this cyanamidate is a stronger hydrogen-bond base than is any nitrile, amine or pyridine. The Bu3N+-N- group increases the basicity of the nitrile group very efficiently because of the conjugation of two lone pairs on the anionic nitrogen with the π systems of the cyano group. This conjugation is also exemplified by the very low ν(C≡N) wavenumber (2104 cm-1).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 449-451 
    ISSN: 0947-3440
    Keywords: Cyclophanes, multifunctionalized ; Auxiliaries, chiral ; Metalation, ortho-directed ; Fries rearrangement ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: For the preparation of the title compound, 4-hydroxy[2.2]paracyclophane (1) is first converted to the carbamate 2. Metalation of 2 with sec-butyllithium yields an ortho-anion which after trapping with dimethylformamide and acidic work-up provides 6 in 64% yield. Further application of the cyclophane anion include its capture by trimethylsilyl chloride to the trimethylsilyl derivative 3 (76%) and its Fries rearrangement to the phenol 4 (78%). The spectroscopic and analytical data of the new compounds are described in full detail.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 57 (1974), S. 602-615 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Die Struktur des Sesquiterpen-γ-Laktons Arteannuin B (1) wurde röntgenographisch und diejenige seines Hydrolyseproduktes (2) durch eine vollständige Analyse des NMR.-Spektrums ermittelt.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 9
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Es wird über eine, bzw. zwei Methoden zur Herstellung von 4-(4′ Methyl-2′-oxo-cyclohex-3′-en-1′-yl)-pentan-1-ol (Schema 1) bzw. 3-(4′-Methyl-2′-oxo-cyclohex-3′-en-1′-yl)-butan-1-olThe IUPAC-Nomenclature of these compounds is: 6-(4′-hydroxy-1′-methyl-butyl)-3-methyl-cyclohex-2-en-1-one and 6-(3′-hydroxy-1′-methyl-propyl)-3-methyl-cyclohex-2-en-1-one.-Derivaten ( Schemata 2 und 3) berichtet. Die Synthesen sind nicht spezifisch bezüglich Diastereoisomerie an den Zentren C(1′) und C(4), bzw. C(1′) und C(3). Als potentielles Terpenoid-Synthon kommt das Produkt der Synthese nach Schema 1 , Schritte (1) bis (3), in Frage.
    Type of Medium: Electronic Resource
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  • 10
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Eine thermische (a) und eine reduktive (b) Methode zur Herstellung von Mikanez-Estern wird beschrieben. Bei der ersten gelang der Nachweis des monomeren Vorläufers, 1,3-Butadien-2-carboxylester. (a)trans/cis-Gemische von Methyl resp. Äthyl 2-Brom-1-methylcyclopropancarboxylat (14/15 resp. 16/17), mit Tri-n-butylzinnhydrid aus den entsprechenden 2,2-Dibrom-1-methylcyclopropancarboxylaten 12 resp. 13 hergestellt, wurden bei 480°/1,7 Torr pyrolysiert. Die bei -78° daraus abgefangenen Kondensate bestanden aus den 1,3-Butadien-2-carboxylaten 5 und 6, im Falle des Äthylesters 6 durch seine 1H-NMR.-Signale charakterisiert und als Addukt (19) mit 4-Phenyl-1,2,4-triazolin-3,5-dion (18) abgefangen (55%). Beim Erwärmen der Kondensate dimerisierten die Dienester 5 resp. 6, so dass sich Dimethyl resp. Diäthyl Mikanezat (9 resp. 10) isolieren liess (67 resp. 100%).(b)Behandlung von Methyl 2(E)-2-Methyl-2-butenoat (20) mit 2 Äquivalenten N-Bromsuccinimid gab (25%) Methyl 2(Z)-4-Brom-2-brommethyl-2-butenoat (21). (Mit 3 Äquivalenten entstand ein Stereomerengemisch 2(Z)- und 2(E)-4,4-Dibrom-2-brommethyl-2-butenoat (22 und 23)). Reduktion des Dibromesters 21 mit Zink in Tetrahydrofuran, Methanol oder Eisessig ergab (50%) Dimethyl Mikanezat (9). Von einer Iodolaktonisierung der aus 9 durch Verseifung hergestellten Mikanezsäure (8) erhielt man 4-Iodo-7-oxo-1-vinyl-6-oxabicyclo[3.2.1]octan-4endo-carbonsäure (24), dessen Bildungsleichtigkeit und IR.-Bande bei 1780 cm eine unabhängige Bestätigung dafür liefert, dass Mikanezsäure (8) durch Kopf-zu-Kopf-Diels-Alder-Dimerisierung von 1,3-Butadien-2-carbonsäure (4) entsteht.Aus Methyl (E)-2-Methyl-2-pentenoat (25) wurde auf gleiche Weise, d.h. über Dibromierung zu 27 und Reduktion mit Zink in Äther, Dimethyl 3,2′-Dimethylmikanezat (29) gewonnen. Die Multiplizität des 1H-NMR.-Signals von H—C(3) in 29 bestätigt, wiederum unabhängig, dass die Dimerisierung des Dienesters (in diesem Fall 28) in Kopf-zu-Kopf-Diels-Alder-Weise stattfindet.
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