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  • 2H,6H,8H-Thiopyrano[4′',3′':4′,5′]thieno[2′,3′:4,5]pyrimido[2,1-b][1,3]thiazin-6-one  (1)
  • 4′-didehydro; 5-Alkoxymethyluracil nucleosides; Human immunodeficiency virus; Herpes simplex virus.  (1)
  • 5-Alkoxymethyluracils  (1)
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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of new fused heterocycles by annelation of thiopyrano[4′,3′:4,5]thieno[2,3-c]pyrimidines (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 953-959 
    Details
    ISSN: 1434-4475
    Keywords: Fused S,N-heterocycles ; Thieno[2,3-c]thiopyrans ; 1,5,6,8-Tetrahydro-2H-thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones ; Thiazolo[3,2-a]thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-5-ones ; 2H,6H,8H-Thiopyrano[4′',3′':4′,5′]thieno[2′,3′:4,5]pyrimido[2,1-b][1,3]thiazin-6-one
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Entsprechend substituierte Thieno[2,3-c]thiopyrane (2, 3, 5, 6, 10, 11) wurden in 1,5,6,8-Tetrahydro-2H-thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one (4, 7, 12) umgewandelt, welche als Schlüssel-Zwischenprodukte für Thiazol- und 1,3-Thiazin-Anellierungen zu den tetracyclischen Zielstrukturen7, 8, 9 und13 dienten; diese leiten sich von zwei neuen heterocyclischen Ringsystemen ab.
    Notes: Summary Appropriately substituted thieno[2,3-c]thiopyrans (2, 3, 5, 6, 10, 11) were converted into 1,5,6,8-tetrahydro-2H-thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones (4, 7, 12). These in turn were used as key intermediates for annelations of thiazolo and 1,3-thiazino moieties to yield the tetracyclic target structures7, 8, 9, and13, derived from two novel heterocyclic ring systems.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00811015
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of 3′-Azido, 2′,3′-Didehydro, and 3′,4′-Didehydro Nucleosides from 5-Alkoxymethyluracils (1998)
    Springer
    Monatshefte für Chemie 129 (1998), S. 99-109 
    Details
    ISSN: 1434-4475
    Keywords: Keywords. Nucleosides ; convergent synthesis of; Nucleosides ; 3′-azido-2′-deoxy; Nucleosides ; 2′ ; 3′-didehydro; Nucleosides ; 3′ ; 4′-didehydro; 5-Alkoxymethyluracil nucleosides; Human immunodeficiency virus; Herpes simplex virus.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung.  Reaktion von Methyl-5-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranosid (3) mit den silylierten 5-Alkoxymethyluracilen 2a–c unter Verwendung von Trimethylsilyltrifluormethansulfonat als Katalysator ergab die α-Nucleoside 4a–c und die β-Nucleoside 5a–c. Die entsprechenden 3′,4′- und 4′,5′-Didehydronucleoside 6–9 wurden durch Behandeln der Jodnucleoside 4a–c oder 5a–c mit 10 Äquivalenten Natriummethoxid in siedendem Methanol über eine Eliminierungsreaktion hergestell. Die entschützten 3′-Azidonucleoside 10a–c und 11a–c vom AZT-Typ wurden ebenso wie die 4′,5′-Didehydronucleoside 7a–c und 9a–c durch Umsetzung von 4a–c und 5a–c mit Natriumazid und nachfolgender Behandlung mit Tetrabutylammoniumfluorid erhalten.
    Notes: Summary.  Reaction of methyl 5-tert-butyldiphenylsilyl-2,3-dideoxy-3-iodo-D-threo-pentofuranoside (3) with silylated 5-alkoxymethyluracils 2a–c using trimethylsilyl trifluoromethanesulfonate as a catalyst afforded the α nucleosides 4a–c and the β nucleosides 5a–c. The corresponding 3′,4′- and 4′,5′-didehydro nucleosides 6–9 were prepared in an elimination reaction by treating the iodo nucleosides 4a–c or 5a–c with 10 equivalents of sodium methoxide in methanol under reflux. The deprotected 3′-azido nucleosides 10a–c and 11a–c of the AZT type as well as the 4′,5′-didehydro nucleosides 7a–c and 9a–c were prepared by treating 4a–c and 5a–c, respectively, with sodium azide and subsequently with tetrabutylammonium fluoride.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00010110
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of 2′,3′-dideoxynucleosides from 5-alkoxymethyluracils (1991)
    Springer
    Monatshefte für Chemie 122 (1991), S. 59-70 
    Details
    ISSN: 1434-4475
    Keywords: 2′,3′-Dideoxycytidines ; 2′,3′-Dideoxyuridines ; 5-Alkoxymethyluracils ; Human immunodeficiency virus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Ausgehend vonL-Glutaminsäure (1) wird eine modifizierte Synthese von geschützter 2,3-Dideoxyribose (5) beschrieben. Reaktion von5 mit silyliertem 5-Alkoxymethyluracilen7 b–e in Gegenwart von Trimethylsilyltriflat ergab anomere Mischungen der 2′,3′-Dideoxyuridinderivate8 a–e und9 a–e. Abspaltung der Schutzgruppe mit methanolischen Ammoniak und chromatographische Trennung ergab die entsprechenden Nucleoside10 a–e und11 a–e. Behandlung von9 b–e mit Tri(1H-1,2,4-triazol-1-yl)phosphinoxid und nachfolgende Reaktion von12 b–e mit Ammoniak in Dioxan ergab die Cytosinderivate13 b–e, welche nach Behandlung mit methanolischem Ammoniak die entsprechenden 2′,3′-Dideoxycytidinderivate14 b–e und15 b–e ergaben. Im Gegensatz zur Stammverbindung hatten diese Alkoxymethylderivate keine nennenswerte Wirksamkeit gegen den menschlichen Immunschwächevirus (HIV-1).
    Notes: Summary A modified synthesis of protected 2,3-dideoxyribose5 starting fromL-glutamic acid (1) is described. Reaction of5 with silylated 5-hydroxymethyluracil7 a and 5-alkoxymethyluracils7 b–e in the presence of trimethylsilyl triflate afforded an anomeric mixture of 2′,3′-dideoxyuridine derivatives8 a–e and9 a–e. Deprotection with methanolic ammonia and separation by chromatography gave the corresponding nucleosides10 a–e and11 a–e. Treatment of9 b–e with tri(1H-1,2,4-triazol-1-yl)phosphine oxide and subsequent reaction of12 b–e with ammonia in dioxane afforded the cytosine derivatives13 b–e which on treatment with methanolic ammonia gave the corresponding 2′,3′-dideoxycytidine derivatives14 b–e and15 b–e. In contrast with the parent compounds, these alkoxymethyl derivatives had no appreciable activity against human immunodeficiency virus (HIV-1).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00815166
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    Paper (German National Licenses)
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