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  • 1
    Electronic Resource
    Electronic Resource
    Antibiotics from basidiomycetes (1981)
    Springer
    Archives of microbiology 130 (1981), S. 223-227 
    Details
    ISSN: 1432-072X
    Keywords: Antibiotics ; Basidiomycetes ; Pleurotellus hypnophilus ; Galerina cephalotricha ; Hypnophilin ; Pleurotellol ; Pleurotellic acid ; Complicatic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Three new antibiotically active metabolites were isolated from cultures of the fungus Pleurotellus hypnophilus. The structures which are closely related to the coriolins were elucidated by spectroscopic methods. Hypnophilin (1) has a hirsutane sceleton whereas pleurotellol (2) and pleurotellic acid (3) are sesquiterpenoids with novel hirsutane skeletons. The common structural feature of all three metabolites is an α-methylene ketone moiety. The antibiotics inhibited the growth of several bacteria as well as of some fungi. In cells of the ascitic form of Ehrlich carcinoma RNA and DNA syntheses were more affected than protein synthesis. The mode of action was compared with the antimicrobial and cytotoxic effects of complicatic acid (4) and other α-methylene ketones and lactones from higher plants. All the compounds tested reacted rapidly with cysteine to form adducts which were almost devoid of biological activity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00459523
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  • 2
    Electronic Resource
    Electronic Resource
    Ungewöhnlicher Verlauf der Reaktion von α-Acyl-γ-butyro-lactonen mit 2-(2,6-Dihalogenphenylimino)imidazolidinen (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 2841-2851 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Unusual Course of the Reaction of α-Acyl-γ-butyrolactones with 2-(2,6-Dihalogenophenylimino)imidazolidinesHeating of α-acyl-γ-butyrolactones 1 with 2-(2,6-dihalogenophenylimino)imidazolidines 5 in HMPT unexpectedly leads to 7-halogeno-2-,6-dihydro-4-alkyl-5,6-ethano-1H- [1,4]diazepino-[1,7-a]benzimidazoles 7 in low yields. The structures of 7 are derived from spectroscopic data, oxidative degradation to benzimidazole derivative 9 and an X-ray structure analysis. A possible pathway for the formation of 7 is discussed.
    Notes: α-Acyl-γ-butyrolactone 1 liefern beim Erhitzen mit 2-(2,6-Dihalogenphenylimino)imidazolidinen 5 in HMPT unerwartet in geringen Ausbeuten 7-Halogen-2,6-dihydro-4-alkyl-5-,6-ethano-1H-[1,4]diazepino[1,7-a]benzimidazole 7, deren Struktur durch die spektroskopischen Daten, Abbauversuche und eine Röntgenstrukturanalyse abgeleitet wird. Der mögliche Bildungsweg dieser Verbindungen wird diskutiert.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130903
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  • 3
    Electronic Resource
    Electronic Resource
    α-Aminosäuren als nucleophile Acyläquivalente, V. Sterisch gelenkte Michael-Addition von Oxazolin-5-on-Anionen an aktivierte Doppelbindungen; Synthese von1,4-Dicarbonylverbindungen und γ-Oxonitrilen (1981)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 114 (1981), S. 2580-2594 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: α-Amino Acids as Nucleophilic Acyl Equivalents, V. Sterically Directed Michael-Addition of Oxazolin-5-one Anions to Activated Double Bonds; Synthesis of 1-4-Dicarbonyl compounds and γ-OxonitrilesOxazolin-5-ones with bulky substituents like mesityl or 1-butylcyclohexyl at C-2 undergo triethyl-amine catalyzed addition to activated olefins exclusively at C-4. Hydrolysis of the derived 4,4-disubstituted 2-mesityl-2-oxazolin-5-ones 9 leads to N-mesitoyl amino acids 10 which yield 1,4-dicarbonyl compounds or γ-oxonitriles 11 on oxidation with lead tetraacetate.
    Notes: Oxazolin-5-one, die in 2-Stellung raumerfüllende Reste wie Mesityl oder 1-Butylcyclohexyl tragen, addieren in Gegenwart von Triethylamin aktivierte Olefine ausschließlich in 4-Stellung. Die so erhaltenen 4,4-disubstituierten 2-Mesityl-2-oxazolin-5-one 9 werden nach Hydrolyse zu den N-Mesitoylaminosäuren 10 mit Bleitetraacetat zu 1,4-Dicarbonylverbindungen oder γ-Oxonitrilen 11 oxidiert.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19811140721
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  • 4
    Electronic Resource
    Electronic Resource
    Thermolyse von Oxazolin-5-onen, X. 3-Imidazoline und Δ3-Tetrahydropyrimidine durch Thermolyse von 3-Oxazolin-5-onen aus N-Acyldipeptiden (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 770-786 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Thermolysis of Oxazolin-5-ones, X. 3-Imidazolines and Δ3-Tetrahydropyrimidines by Thermolysis of 3-Oxazolin-5-ones Derived from N-Acyl DipeptidesOn thermolysis 2-(acylaminomethyl)-3-oxazolin-5-ones (3a - g) undergo elimination of CO2 to give nitrile ylides which cyclize to 3-imidazolines 4a - g via intramolecular proton transfer. The 2-acylaminoethyl derivative 3h yields a Δ3-tetrahydropyrimidine 5h in an analogous manner. Compounds 3 may be easily obtained from N-acyl dipeptides 1. The temperature dependence of the 1H NMR spectra of 4 is discussed.
    Notes: Die Thermolyse von 2-(Acylaminomethyl)-3-oxazolin-5-onen (3a - g) führt unter Eliminierung von CO2 zu Nitril-yliden, welche nach innermolekularer Protonenübertragung zu 3-Imidazolinen 4a - g cyclisieren. Analog liefert das 2-(Acylaminoethyl)-Derivat 3h ein Δ3-Tetrahydropyrimidin 5h. Die Oxazolinone 3 sind aus N-Acyldipeptiden 1 leicht zugänglich. Die Temperaturabhängigkeit der 1H-NMR-Spektren von 4 wird diskutiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130234
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  • 5
    Electronic Resource
    Electronic Resource
    Reaktionen von Oxazolin-5-on-Anionen, IX. Ein einfaches Verfahren zur Darstellung von Derivaten der δ-Aminolävulinsäure und verwandter Verbindungen (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 787-790 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Oxazolin-5-one Anions, IX. A Simple Procedure for the Preparation of δ-Aminolevulinic Acid Derivatives and Related CompoundsCyclization of Z-dipeptides 1 with acetic anhydride leads to 2-oxazolin-5-ones, which yield the corresponding 3-oxazolin-5-ones 2 by base-catalyzed addition of ethyl acrylate or acrylonitrile. Hydrolysis of 2a gives ethyl δ-(benzyloxycarbonylamino)levulinate (3a), which may be converted into several N-protected derivatives 3e - i. Via the same procedure the homologue 3b and the nitriles 3c, d are easily obtained.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130235
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  • 6
    Electronic Resource
    Electronic Resource
    α-Aminosäuren als nucleophile Acyläquivalente, IV. Synthese symmetrischer Ketone unter Verwendung von 2-Phenyl-2-oxazolin-5-on (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 3706-3715 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: α-Amino Acids as Nucleophilic Acyl Equivalents, IV. Synthesis of Symmetrical Ketones by Means of 2-Phenyl-2-oxazolin-5-one2-Phenyl-2-oxazolin-5-one (2), itself easily derivable from hippuric acid (1), on reaction with allyl, benzyl or phenacyl halides undergoes 4,4-disubstitution, if the reaction is conducted in dipolar aprotic solvents in presence of weak bases. Hydrolysis of the resulting oxazolinones 3 leads to α, α-dialkylated hippuric acids 4, which may be oxidized to symmetrical ketones 5 by means of lead tetraacetate.
    Notes: Das aus Hippursäure (1) leicht zugängliche 2-Phenyl-2-oxazolin-5-on (2) wird von Allyl-, Benzyl-oder Phenacylhalogeniden in 4-Stellung doppelt substituiert, wenn die Reaktion in dipolar aprotischen Lösungsmitteln in Gegenwart schwacher Basen durchgeführt wird. Hydrolyse der erhaltenen Oxazolinone 3 liefert α, α-disubstituierte Hippursäuren 4, die mit Bleitetraacetat zu symmetrischen Ketonen 5 oxidiert werden.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801131204
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  • 7
    Electronic Resource
    Electronic Resource
    Untersuchungen zur Reaktion von Acylaminobrommalonestern und Acylaminobromessigestern mit Trialkylphosphiten - eine einfache Synthese von 2-Amino-2-(diethoxyphosphoryl)essigsäure-ethylester (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 599-609 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of Acylaminobromomalonates and Acylaminobromoacetates with Trialkylphosphites - A Simple Synthesis of Ethyl 2-Amino-2-(diethoxyphosphoryl)acetateDepending on the reaction conditions acylaminobromomalonates 1 and trialkylphosphites yield either 5-alkoxyoxazoles 7, 2-[acyl(dialkoxyphosphoryl)amino]malonates 8, or 2-acylamino-2-(dialkoxyphosphoryl)malonates 2. N-Acylglycin esters 9 can be converted into the corresponding α-bromo derivatives 10 by treatment with bromine or N-bromosuccinimide. Treatment of 10 with trialkylphosphites yields 2-acylamino-2-(dialkoxyphosphoryl)acetates 12. Removal of the protecting groups from the Boc or trichloroethoxycarbonyl derivatives 12g and 12h, respectively, leads to ethyl 2-amino-2-(diethoxyphosphoryl)acetate (11). Reaction of 10a with triphenylphosphane yields the phosphonium salt 14a which is converted into the 2,3-bis(benzoylamino)fumarate 18 by action of base.
    Notes: In Abhängigkeit von den Reaktionsbedingungen liefern Acylaminobrommalonester 1 mit Trialkylphosphiten entweder 5-Alkoxyoxazole 7, 2-[Acyl(dialkoxyphosphoryl)amino]malonester 8 oder 2-Acylamino-2-(dialkoxyphosphoryl)malonester 2. N-Acylglycinester 9 können mit Brom oder N-Bromsuccinimid in die α-Bromderivate 10 übergeführt werden, die mit Trialkylphosphiten glatt die 2-Acylamino-2-(dialkoxyphosphoryl)essigester 12 ergeben. Durch Entfernen der Schutzgruppen aus den Boc- und Trichlorethoxycarbonyl-Derivaten 12g und 12h ist 2-Amino-2-(diethoxyphosphoryl)essigsäure-ethylester (11) zugänglich. Das durch Umsetzung von 10a mit Triphenylphosphan erhältliche Phosphoniumsalz 14a erleidet bei Baseneinwirkung eine Dimerisierung zum 2,3-(Bisbenzoylamino)fumarat 18.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830409
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  • 8
    Electronic Resource
    Electronic Resource
    Umwandlung phenolischer α-Aminosäuren in α-Ketosäuren (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1638-1639 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Conversion of Phenolic α-Amino Acids into α-Keto acidsA one-pot conversion of tyrosine (1a) and 3,4-dihydroxyphenylalanine (DOPA) (1b) into 3-(4-hydroxyphenyl)pyruvic acid (2a) and 3-(3,4-dihydroxyphenyl)pyruvic acid (2b), respectively, via 2-trifluoromethyl-3-oxazolin-5-ones 5 is described.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830918
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  • 9
    Electronic Resource
    Electronic Resource
    Pilzpigmente, 41. Naphthochinon-Farbstoffe aus den Schleimpilzen Trichia floriformis und Metatrichia vesparium (Myxomycetes) (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 1722-1729 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fungus Pigments, 4141).  -  Naphthoquinone Pigments from the Slime Moulds Trichia floriformis and Metatrichia vesparium (Myxomycetes)Trichione (1) is the red main pigment of fruiting bodies from the slime mould Trichia floriformis. It contains a 2,5-dihydroxynaphthoquinone chromophore, substituted in position 3 by an unsaturated side chain carrying a terminal hemimalonate moiety. Homotrichione (7) differs by the presence of two additional CH2 groups in the side chain. It co-occurs with arcyriaflavin B (5), arcyriaflavin C (6) and further pigments in Metatrichia vesparium.
    Notes: Die Fruchtkörper des Schleimpilzes Trichia floriformis enthalten als roten Hauptfarbstoff Trichion (1), ein 2,5-Dihydroxynaphthochinon, das in 3-Stellung eine ungesättigte Seitenkette mit terminaler Malonhalbester-Gruppierung trägt. Homotrichion (7) unterscheidet sich nur durch eine um zwei CH2-Gruppen längere Seitenkette. Es kommt neben 1, Arcyriaflavin B und C (5 bzw. 6) und weiteren Farbstoffen in Metatrichia vesparium vor.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820913
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  • 10
    Electronic Resource
    Electronic Resource
    1,2-Naphthochinon-Derivate aus Kulturen des Mycosymbionten der Flechte Trypethelium eluteriae (Trypetheliaceae) (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 779-785 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 1,2-Naphthochinon-Derivate from Cultures of the Mycosymbiont from the Lichen Trypethelium eluteriae (Trypetheliaceae)From cultures of the mycosymbiont of the tropical cortical lichen Trypethelium eluteriae Sprengel the antibiotically active 1,2-naphthoquinones trypethelone (2), trypethelone methyl ether (3), 8-methoxytrypethelone methyl ether (5), and 4′-hydroxy-8-methoxytrypethelone methyl ether (6) have been isolated. The substitution pattern of these new derivatives of (+)-dunnione (1) is in accord with a polyketide biogenesis of the quinone system.
    Notes: Aus Kulturen des Mycosymbionten der tropischen Rindenflechte Trypethelium eluteriae Sprengel wurden die antibiotisch aktiven 1,2-Naphthochinone Trypethelon (2), Trypethelon-methylether (3), 8-Methoxytrypethelon-methylether (5) und 4′-Hydroxy-8-methoxytrypethelon-methylether (6) isoliert. Es handelt sich um Derivate des (+)-Dunnions (1), deren Substituentenanordnung mit einer Polyketidbiogenese des Chinonsystems im Einklang ist.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800517
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