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  • 1
    Electronic Resource
    Electronic Resource
    High-affinity binding sites for juvenile hormone I in the larval integument of Drosophila hydei (1980)
    [s.l.] : Nature Publishing Group
    Nature 286 (1980), S. 282-285 
    Details
    ISSN: 1476-4687
    Source: Nature Archives 1869 - 2009
    Topics: Biology , Chemistry and Pharmacology , Medicine , Natural Sciences in General , Physics
    Notes: [Auszug] Because it has been established that receptors for steroid hormones in vertebrates2 and invertebrates, especially the fruitfly Drosophila3'4 and the crayfish Orconectes5, exist in the cytosol of target cells in only very low concentrations, we started our search for receptors of the non-steroid JH ...
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1038/286282a0
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  • 2
    Electronic Resource
    Electronic Resource
    Biphenyltetrols and Dibenzofuranones from Oxidative Coupling of Resorcinols with 4-Alkylpyrocatechols: New Ciues to the Mechanism of Insect Cuticle Sclerotization (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1205-1212 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oxidation of 4-alkylpyrocatechols 2 by means of an insect diphenoloxidase (laccase) or K3 [Fe(CN)6] yields, in the presence of resorcinols 1 (R2 = H), complex mixtures of products from which biphenyltetrols 3 (R3 = H) and dibenzofuranones 5 and 6 were isolated. It is suggested that similar homo-coupling products are formed from pyrocatechols 2b and 2c in insects during cuticle sclerotization.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740607
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis and Enzyme-Inhibition Studies of Phenylsemicarbazones derived from D-glucono-1,5-lactone and 2-acetamido-2-deoxy-D-glucono-1,5-lactone (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 323-334 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The carbohydrate-derived lactone phenylsemicarbazones 3 and 4 were prepared from 5 and 8 (Scheme). Treatment with 4-phenylsemicarbazide gave 6 and 7 (77:23) and 9 and 19 (76:24), respectively. Oxidation of 6 and 9 by CrO3-pyridine to 11 and 13, followed by deprotection, yeilded 3 and 4. The structure of 3 was established by X-ray analysis. Enzyme-inhibition studies using revealed that 3 is a competitive inhibitor with Ki = 23 μm. The activity of 4 was examined using N-acetylglucosaminidase from bovine kidney, Aspergillus niger, and Artemia salina. compound 4 was found to be a competitive inhibitor of all three enzymes with Ki values of 0.13, 6.0, and 0.71 μm and KM/Ki values of 6910, 45, and 465, respectively.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750129
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesen von Galactose-Cluster-haltigen Steroid-DerivatenAuszugweise vorgetragen auf der Chemiedozenten-Tagung, Bielefeld, 7, März 1989. (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 863-869 
    Details
    ISSN: 0170-2041
    Keywords: Glycoconjugates ; Galactosides ; Steroid esters ; Amphiphiles ; Glycopeptides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Galactose-Cluster-Containing Steroid DerivativesThe synthesis of galactose clusters that are linked to a steroid moiety by a peptide-like spacer unit is described. The galactose cluster is obtained by Koenigs-Knorr glycosylation of TRIS-Gly-Fmoc (2b) under Helferich conditions. Peptide and ester bonds are formed after activation of carboxylic acids as diphenylthiophene dioxide (TDO) esters. 6a is synthesized in a convergent way by coupling of (Ac4Gal)3-TRIS-Gly (3e) with cholesteryl TDO succinate (5b). Coupling of (Ac4Gal)3-TRIS-Gly hydrogen succinate (3f) with Gly-O-Chol (5d) by means of EEDQ yields 6d. Reaction of (Ac4Gal)3-TRIS-Gly-SUCC-O-TDO (3g) with 25-hydroxycholesterol leads in a linear sequence to the oxysterol derivative 6f. Selective cleavage of the acetyl groups from galactose units yields the known compound 6b and the new derivatives 6e and 6g.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001162
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  • 5
    Electronic Resource
    Electronic Resource
    Preparation of the N-Acetylglucosaminidase Inhibitor 1-Acetamido-1,2,5-trideoxy-2,5-imino-D-glucitol from Methyl α-D-Mannopyranoside (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 555-561 
    Details
    ISSN: 0170-2041
    Keywords: Aza sugars ; Glycosidase inhibitors ; Piperidine ring contraction ; Pyrrolidines ; Enzymes ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Fragmentation of methyl 3-O-benzyl-6-bromo-2-O-(tert-butyldimethylsilyl)-6-deoxy-4-O-(4-methoxybenzyl)-α-D-mannopyranoside (2) and in situ reductive amination give (3R,4S,5R)-6-benzylamino-4-benzyloxy-5-(tert-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)hexene (3) which is converted by intramolecular aminomercuration into an epimeric mixture of the bromomercuriopiperidine derivatives 4 and 5. The minor D-manno epimer 4 is transformed into mesylate 10 which, upon reaction with LiN3 in DMF, suffers a piperidine-pyrrolidine ring contraction to give azidomethylpyrrolidine 11. Reductive acetylation by means of thioacetic acid affords the fully protected pyrrolidine aza sugar derivative 12. The major L-gulo epimer 5 is transformed into the mesylate 15 which, again, upon reaction with LiN3 in DMF undergoes piperidine-pyrrolidine ring contraction to give the 1-azido-3-O-benzyl-2,5-benzylimino-6-bromomercurio-1,2,5,6-tetradeoxy-4-O-(4-methoxybenzyl)-L-iditol (16). Eliminative dehalomercuration by means of Zn powder is accompanied by in situ reduction of the azido group to give amino alkene 17. Intramolecular aminomercuration of 17 followed by N-acetylation yields the protected 1,2,5,6-tetradeoxy-2,5-imino-D-glucitol derivative 20 as the major epimer. Reductive oxygenation of 20 leads to pyrrolidine 22 which is deprotected to give title compound 1. Selective cleavage of the PMB group of 22 leads to 24. Benzylation of 22 affords again 12 from which the OH group at C-4 is liberated by selective cleavage of the PMB ether to give pyrrolidine 13. Compound 1 inhibits NAGase from bovine kidney.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940605
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis of Dopamines Labelled with 13C in the α- or β-Side Chain Position and Their Application to Structural Studies on Melanins by Solid-State NMR SpectroscopyDedicated to Professor Peter Karlson on the occasion of his 75th birthday. (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 563-567 
    Details
    ISSN: 0170-2041
    Keywords: CP-MAS NMR Spectroscopy ; Melanin ; Oxidative phenolic coupling ; Quinone methides ; Labelled compounds, 13C ; Dopamines ; Enzymes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Solid-state NMR spectroscopy was applied to the analysis of melanins prepared by peroxidase-H2O2 oxidation of dopamines specifically 13C labelled in the α- or β-side chain positions. A surprisingly diverse pattern of signals indicated the presence of uncyclized dopamine and noradrenaline-derived units, in addition to indole and carbonyl carbon atoms. These structural features, coupled with the results obtained from elemental analysis of dopamine melanin samples prepared under different conditions, point to a pigment formation process more complex than previously believed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940606
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of Aryl Azide Analogues of Insect Juvenile Hormones as Reagents for the Photoaffinity Labeling of Juvenile Hormone Binding Proteins (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 327-331 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese von Arylazid-Analogen der Juvenilhormone von Insekten als Reagenzien für die Photoaffinitätsmarkierung von Juvenilhormon-bindenden Proteinen.Es werden Synthesen der Azidophenyl-6,7-epoxygeranylether rac-4c und rac-4d sowie des Azidobenzoates rac-6 beschrieben. p-Azidophenyl-6,7-epoxygeranylether (rac-4c) zeigt eine hohe Bindungsaffinität zu dem in der Wanderheuschrecke Locusta migratoria vorkommenden Juvenilhormon-Bindungsprotein. Bestrahlung bei 254 nm oder bei 300 nm führt zu rascher Photolyse. rac-4c wird als neues Reagenz zur Untersuchung von Juvenilhormon-bindenden Proteinen aus solchen Insektenspezies, deren natürliches Hormon 1a ist, vorgeschlagen. Weiterhin werden Synthesen und Bindungseigenschaften des Arylketons rac-4e und des Vinylketons rac-7 beschrieben.
    Notes: The azidophenyl 6,7-epoxygeranyl ethers rac-4c and rac-4d and the azidobenzoate rac-6 were synthesized. p-Azidophenyl 6,7-epoxygeranyl ether (rac-4c) shows a high affinity to the juvenile hormone binding protein of the migratory locust, Locusta migratoria. Fast photolysis is observed upon irradiation at 254 nm and at 300 nm. It is proposed that rac-4c is useful as a new reagent for the study of juvenile hormone binding proteins of insects in which the natural hormone is 1a. The synthesis and binding properties of the aryl ketone rac-4e and the vinyl ketone rac-7 are described also.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870329
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  • 8
    Electronic Resource
    Electronic Resource
    N-Acylcatecholamine und 3,4-Dihydro-6,7-isochinolindiole aus N-Acyl-3,4-dimethoxyphenethylaminen (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1189-1193 
    Details
    ISSN: 0170-2041
    Keywords: Catecholamines ; Isoquinolinediols ; Bischler-Napieralski reaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: N-Acylcatecholamines and 3,4-Dihydro-6,7-isoquinolinediols from N-Acyl-3,4-dimethoxyphenethylaminesThe N-[2-(3,4-dimethoxyphenyl)ethyl]acetamides 2a and 2e are cleaved with boron tribromide to yield as expected the catechols 3a and 3e whereas, under the same conditions, mixtures of the catechols 3b, 3c, 3f, or 3g and 1-(haloalkyl)dihydroisoquinolines 4b, 4c, 4f, or 4g are formed from the corresponding halogenated acetamides 2b, 2c, 2f, and 2g, respectively. The trifluoracetamide 2d yields exclusively the cyclization product 4d. Since higher halogenated 1-(haloalkyl)-3,4-dihydroisoquinolines are formed in the Bischler-Napieralski reaction - if at all - under quite drastic conditions only, the use of boron tribromide provides a new entry into this series.
    Notes: Die N-[2-(3,4-Dimethoxyphenyl)ethyl]acetamide 2a und 2e liefern mit Bortribromid erwartungsgemäß die Catechole 3a bzw. 3e, während aus den halogenierten Acetamiden 2b, 2c, 2f und 2g Mischungen aus den korrespondierenden Catecholen 3b, 3c, 3f bzw. 3g und den 1-(Halogenalkyl)dihydroisochinolinen 4b, 4c, 4f, bzw. 4g entstehen. Das Trifluoracetamid 2d liefert ausschließlich das Dihydro-1-(trifluormethyl)isochinolin 4d. Da höher halogenierte 1-(Halogenalkyl)-3,4-dihydroisochinoline mit der Bischler-Napieralski-Reaktion - wenn überhaupt - nur unter drastischen Reaktionsbedingungen zugänglich sind, bietet die Verwendung von BBr3 eine neue Möglichkeit zur Herstellung dieser Verbindungen.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890290
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  • 9
    Electronic Resource
    Electronic Resource
    Chemische Modifikation von Biopolymeren durch Chinone und Chinonmethide (1989)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 101 (1989), S. 572-587 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chinone und Vorstufen, die oxidativ in Chinone und/oder Chinonmethide umgewandelt werden können, sind in der Natur weit verbreitet. Als sekundäre Naturstoffe wirken sie häufig antibiotisch, cytotoxisch, aber auch pathogen, und eine Reihe von Pflanzen und Tieren benutzt chinoide Substanzen als Abwehrstoffe, oft mit spektakulärem Erfolg. Auf makromolekularer Ebene spielen Chinonmethide im Pflanzenreich eine Schlüsselrolle bei der Biosynthese von Lignin, während die Bildung von Melanoproteinen ein Beispiel für Reaktionen von o-Chinonen im Tierreich ist. Bei den Insekten dienen Chinone und Chinonmethide zur Bildung des lebensnotwendigen Exoskeletts. Die Reaktivität von Chinonen in biologischen Systemen hat auch für den Menschen unmittelbare Bedeutung in pharmazeutischer, toxikologischer und technologischer Hinsicht. Den Beispielen in diesem Aufsatz liegt ein gemeinsames Prinzip zugrunde, nämlich die chemische Modifikation von Biopolymeren durch Chinone und Chinonmethide. Wie sich besonders bei einer detaillierteren Betrachtung der Reaktionen zeigt, die zur Sklerotisierung der Insektencuticula führen, sind in den letzten Jahren wichtige neue Erkenntnisse hinzugekommen, die vor allem durch die modernen Methoden der Stofftrennung und der Festkörper-NMR-Spektroskopie ermöglicht worden sind.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19891010505
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  • 10
    Electronic Resource
    Electronic Resource
    The Chemistry of the Quinonoid Compounds. Vol. 2. Part 1 und 2. Herausgegeben von S. Patai und Z. Rapporport. Wiley, Chichester 1987. Part 1: XIV, S. 1-878, geb. £ 175.00. - ISBN 0-471-91285-9; Part 2: XIV, S. 879-1711, geb. £ 175.00. - ISBN 0-471-91914-4 (Beide Bände zusammen £ 325.00. - ISBN 0-471-91916-0) (1989)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 101 (1989), S. 649-650 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19891010532
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