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  • Carbohydrates  (2)
  • Catecholamines  (1)
  • Chitinase  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of N-Acetylglucosaminyl and Diacetylchitobiosyl Amides of Heterocyclic Carboxylic Acids as Potential Chitinase Inhibitors (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2293-2297 
    Details
    ISSN: 1434-193X
    Keywords: Carboxylic acid amides ; Chitinase ; Chitobiose ; Heterocycles ; Enzyme inhibitors ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-(Dimethylamino)oxazoline-4-carboxylic acids 5 were prepared by condensation of binucleophilic amino acids 4and O-ethyl-N,N-dimethylisourea 3. New heterocyclic N-acetylglucosaminyl amides and chitobiosyl amides 8 were obtained by the coupling of tetraacetylglucosamine 6a or heptaacetylchitobiosylamine 6b with acid chlorides of heterocyclic carboxylic acids 2 or 5a and subsequent deacetylation. Based on their substitution patterns, compounds 8were expected to have inhibitory activity towards chitinases. Enzyme assays showed that glycosyl amides 8 indeed were moderate inhibitors of chitinases, the diacetylchitobiosyl amides 8d-f generally having higher inhibitory activities than the N-acetylglucosaminyl amide derivatives 8a-c. Inhibitory activities depended on the chitinase tested.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    Asymmetric Induction in the Epoxidation of Alkenyl Glycosides of Tri-O-acetyl-N-acetyl-β-D-glucosamine (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 1275-1279 
    Details
    ISSN: 0170-2041
    Keywords: Asymmetric induction ; Carbohydrates ; Epoxidation ; Glycosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of alkenyl glycosides 2a-2c with MCPBA gives diasteroisomeric mixtures of epoxides 3 and 4. The asymmetric induction decreases in the order 2a ≫ 2b 〉 2c. The absolute configuration of epoxyalkyl glycosides is determined by correlation with (R)-glycerinaldehyde in an independent synthesis of 3a and 3c.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201211
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  • 4
    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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