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  • Nucleosides, 2′,3′-dideoxy-  (2)
  • 2-(5-triazeno)pyrazole; Human immunodeficiency virus; Herpes simplex virus.  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of Triazenopyrazole Derivativesas Potential Inhibitors of HIV-1 (1999)
    Springer
    Monatshefte für Chemie 130 (1999), S. 1167-1173 
    Details
    ISSN: 1434-4475
    Keywords: Keywords. Triazenopyrazoles; Nucleosides ; convergent synthesis of; Nucleosides ; 1-(5-triazeno)pyrazole; Nucleosides ; 2-(5-triazeno)pyrazole; Human immunodeficiency virus; Herpes simplex virus.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung.  Ethoxymethylenmalonitril und Bis(methlthio)methylenmalonitril wurden mit Hydrazinhydrat zu 5-Aminopyrazol-4-carbonitril (3a) und 5-Amino-3-methyltiopyrazol-4-carbonitril (3b) umgesetzt. Behandlung mit salpetriger Säure und Kupplung mit verschiedenen sekundären Aminen ergab die Triazenopyrazole 4a–j. 5-(3,3-Diethyl-1-triazeno)pyrazol-4-carbonitril (4c) wurde in seine beiden regioisomeren 2-Deoxyribonucleoside 5a,bübergeführt, welche anschließend mit H2O2/OH− zu den entsprechenden Carboxamiden 6a,b hydrolysiert wurden. Alle hergestellten Verbindungen wurden auf ihre biologische Aktivität gegenüber HIV-1 und Herpes simplex getestet. Nur 4c zeigte geringfügige Aktivität gegenüber HIV-1 (ED 50=32μM).
    Notes: Summary.  Ethoxymethylenemalononitrile and bis(methylthio)methylenemalononitrile were condensed with hydrazine hydrate to yield 5-aminopyrazole-4-carbonitrile (3a) and 5-amino-3-methylthiopyrazole-4-carbonitrile (3b), respectively. These compounds were treated with nitrous acid and coupled with different secondary amines to yield the triazenopyrazoles 4a–j. 5-(3,3-Diethyl-1-triazeno)pyrazole-4-carbonitrile (4c) was transferred into its two regioisomeric 2-deoxyribose nucleosides 5a,b which were subsequently hydrolyzed with H2O2/OH− to give the corresponding carboxamides 6a,b. All synthesized compounds were tested for biological activity against HIV-1 and herpes simplex virus, but only 4c showed moderate activity against HIV-1 with ED 50=32μM.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00010295
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  • 2
    Electronic Resource
    Electronic Resource
    A new route to 2′,3′-dideoxycytidine (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 599-602 
    Details
    ISSN: 0170-2041
    Keywords: Glycosidation ; 4-Biphenylcarbonyl protecting group ; Barton deoxygenation ; 2′,3′-Dideoxycytidine ; Nucleosides, 2′,3′-dideoxy- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Deoxy-D-ribose (1) was converted into its methyl glycofuranoside 2, which was treated with 4-biphenylcarbonyl chloride to give a separable mixture of 3 (26%) and 4 (40%). Compounds 3 and 4 were deoxygenated by Barton deoxygenation to give the corresponding 2,3-dideoxyribose derivatives 7 and 8 in good yields as crystalline materials. Reaction of 7 and 8 with the silylated N4-isobutyrylcytosine 9, using trimethylsilyl triflate as catalyst afforded a separable mixture of the protected 2′,3′-dideoxynucleosides 10 (29%) and 11 (31%) which were deprotected with methanolic ammonia to give 2′,3′-dideoxycytidine (12) and its α-anomer 13.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001110
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of 6-dimethylaminopurine 2′,3′-dideoxynucleosides (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 879-883 
    Details
    ISSN: 0170-2041
    Keywords: Nucleosides, convergent synthesis ; Nucleosides, 2′,3′-dideoxy- ; Nucleosides, 2′,3′-didehydro- ; Adenine, N6N6-dimethylnucleosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The trimethylsilyated 6-dimethylaminopurine 1 was coupled with the 2′,3′-dideoxyribose derivatives 2a, b and 7 by using trimethylsilyl triflate as catalyst to yield the corresponding nucleosides 3a, b, 4a, b and 8, which were appropriately deprotected to give the desired nucleosides 5a, b and 9 as well as the related α-isomers 6a, b and 10. The 2-deoxyribose derivative 12 was mesylated at the 3′-O-position to give 13 which was coupled similarly with 1 to yield compound 14 and its α-anomer 15. Compounds 14 and 15 were treated with tetrabutylammonium fluoride to give the desired 2′,3′-didehydro-2′,3′-dideoxynucleoside analogue 16 and its α-anomer 17.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101152
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