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  • Organic Chemistry  (6)
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  • 1
    Electronic Resource
    Electronic Resource
    Die Struktur von Cyclosporin CHerrn Prof. C. A. Grob zum 60. Geburtstag gewidmet (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 1247-1255 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Structure of Cyclosporin CThe structure of cyclosporin C (2), a minor antifungal metabolite from Trichoderma polysporum (Link ex Pers.) RIFAI has been elucidated. Hydrolytic cleavage and spectroscopic evidence show that cyclosporin C is a neutral oligopeptide of 11 amino acids linked together in a 33-membered ring. Cyclosporin C (2) differs from the main metabolite cyclosporin A (1) [2] [4] only by containing L-threonine in the place of L-α-aminobutyric acid as has been shown by the conversion of 2 into 1. 13C-NMR. spectra and study of molecular models suggest that cyclosporin C (2) has the same molecular conformation as 1, which is best described as a twisted β-pleated sheet held together in a conformationally stable form by intramolecular hydrogen bonding.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600414
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  • 2
    Electronic Resource
    Electronic Resource
    Zur Struktur des Scillicyanosids. 57. Mitteilung über Herzglykoside (1973)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 56 (1973), S. 2088-2094 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Based on chemical and NMR. evidence structure 1 is assigned to the cardioactive scillicyanoside isolated from white squill.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19730560634
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  • 3
    Electronic Resource
    Electronic Resource
    Die Konstitution der isomeren Acetyldigitoxine. 48. Mitteilung über Herzglykoside (1962)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 45 (1962), S. 881-900 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction with phenylisocyanate transformed both acetyldigitoxin-α and acetyldigitoxin-β into their tris-phenylurethanes (I and IX, respectively). By degradation of these derivatives, the constitutions of the degluco-lanatosides could be elucidated. In acetyldigitoxin-α, the characteristic acetyl group is attached to C-3 of the terminal digitoxose unit, while the acetyl group of acetyldigitoxin-β is located at C-4 of the terminal sugar. The reversible rearrangement of the isomeric acetyl-digitoxins represents an acyl migration.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19620450318
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  • 4
    Electronic Resource
    Electronic Resource
    Zur Struktur der Scilliglaucosids. 56. Mitt. über Herzglykosided (1973)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 56 (1973), S. 2083-2087 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The structure of scilliglaucoside, a cardiac active squill glycoside, is revised. The assignment of the new structural formula 1 is made on the basis of NMR. spectral data.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19730560633
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  • 5
    Electronic Resource
    Electronic Resource
    Vergleich der Produkte aus der Reaktion von Phenylguanidin-Derivaten mit β-Ketoestern bzw. Propiolsäureestern (Synthese von Pyrimidonen) (1976)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 59 (1976), S. 1203-1212 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Comparison of reaction products afforded by phenylguanidine derivatives with β-ketoesters or propiolic esters, respectively (synthesis of pyrimidones).2-Anilino-imidazolines, when treated with either β-ketoesters or propiolic esters, yield two isomeric groups of pyrimidones. The isomerism is based on different positions of the carbonyl group in the pyrimidone ring. The mass spectra permit an unequivocal assignment of constitution I to the product formed with β-ketoesters and of constitution V to that formed with propiolic esters. Additionally, 2-(2-amino-anilino)-2-imidazoline (XII) when treated with methyl phenylpropiolate yields IX; while treatment with ethyl benzoylacetate yields XIII as an intermediate, which eliminates spontaneously one molecule of water to give the benzimidazole derivative XIV. Phenylguanidines (XV) add propiolic esters in the same way as do imidazoline derivatives. Photochemical cleavage of two carbon atoms with their adherent hydrogen atoms from the imidazole ring of the pyrimidones (V) leads to aminopyrimidine derivatives, e.g. XVI.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19760590422
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  • 6
    Electronic Resource
    Electronic Resource
    Cyclosporin A, ein immunsuppressiv wirksamer Peptidmetabolit aus Trichoderma polysporum (LINK ex PERS.) Rifai (1976)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 59 (1976), S. 1075-1092 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyclosporin A, a Peptide Metabolite from Trichoderma polysporum (LINK ex PERS.) Rifai, with a remarkable immunosuppressive activityTwo antifungal metabolites, cyclosporins A and C, were isolated from a strain of Trichoderma polysporum (LINK ex PERS.) Rifai. Cyclosporin A, the main component, has the molecular formula C62H111N11O12 as deduced by NMR. and mass spectra. Hydrolytic cleavage of cyclosporin A furnished 11 amino acids as fragments, among them an artefact of a new C9-amino acid. The amino acid sequence was determined by Edman degradation of iso-cyclosporin A, a basic rearrangement product formed from cyclosporin A by N, O-acyl migration. In an independent investigation an X-ray analysis of the iodo derivative 10 was performed (see the following paper). On the basis of the chemical, spectroscopic and crystallographic evidence the complete structure of cyclosporin A was elucidated as the neutral cyclic oligopeptide 1. Cyclosporin A and C show remarkable immunosuppressive and antiphlogistic activities in several pharmacological models.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19760590412
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