Library

X
feed icon rss

Your email was sent successfully. Check your inbox.

An error occurred while sending the email. Please try again.

Proceed reservation?

Export
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of 2-O-ethyl analogues of 3′-azido- and 3′-fluoro-2′,3′-dideoxyuridines and evaluation of their biological activity against HIV (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 811-817 
    Details
    ISSN: 1434-4475
    Keywords: Nucleosides ; convergent synthesis of ; Uridines, 2-O-ethyl ; Uridines, 2′,3′-dideoxy-3′-fluoro ; AZT analogues ; Human immunodeficiency virus ; Herpes simplex virus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung 2-O-Ethyluracil und 2-O-Ethylthymin wurden mit 1,1,1,3,3,3-Hexamethyldisilazan silyliert und in Gegenwart vonTMS-triflat mit 2,3-Dideoxy-3-fluoro-D-erythro-pentofuranosid, 3-Azido-2,3-dideoxy-D-erythro-pentofuranosid und 2,3-Dideoxy-3-phthalimido-β-D-erythro-pentofuranosederivaten zu den entsprechenden 2-O-Ethyl-Nucleosiden umgesetzt. Entfernung der Schutzgruppe mit gesättigter methanolischer Ammoniaklösung lieferte 2′,3′-Dideoxy-3′-fluor-2-O-ethyluridin; 3′-Azido-2′,3′-dideoxy-3-O-ethyl-uridin wurde durch Entschützung mit Tetrabutylammoniumfluorid in Tetrahydrofuran erhalten. 3′-Amino-2′,3′-dideoxy-3-O-ethyl-uridin konnte nur durch Behandeln des entsprechenden 3′-Azido-Nucleosids mit Triphenylphosphin in Pyridin hergestellt werden. 3′-Deoxy-2-O-ethyl-3′-fluor-thymidin (6b) zeigt geringe Aktivität gegenüber HIV-1.
    Notes: Summary 2-O-Ethyluracil and 2-O-ethylthymine were silylated with 1,1,1,3,3,3-hexamethyldisilazane and condensed in the presence ofTMS triflate with 2,3-dideoxy-3-fluoro-D-erythro-pentofuranoside, 3-azido-2,3-dideoxy-D-erythro-pentofuranoside, and 2,3-dideoxy-3-phthalimido-β-D-erythro-pentofuranose derivatives to give the corresponding 2-O-ethyl nucleosides. Deprotection with saturated methanolic ammonia afforded the 2′,3′-dideoxy-3′-fluoro-2-O-ethyluridines, whereas 3′-azido-2′,3′-dideoxy-3-O-ethyluridine was obtained by deprotection with tetrabutylammonium fluoride in tetrahydrofuran. 3′-Amino-2′,3′-dideoxy-3-O-ethyluridine could be obtained only by treatment of the corresponding 3′-azido nucleoside with triphenylphosphine in pyridine. 3′-Deoxy-2-O-ethyl-3′-fluorothymidine (6b) showed moderate activity against HIV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807175
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of 3′-deoxy-3′-fluoro and -3′-amino nucleosides from 2-methylthiopyrimidin-4(1H)-ones (1996)
    Springer
    Monatshefte für Chemie 127 (1996), S. 979-988 
    Details
    ISSN: 1434-4475
    Keywords: Nucleosides, convergent synthesis of ; Nucleosides, 2′,3′-dideoxy-3′-fluoro ; Nucleosides, 2′,3′-dideoxy-3′-amino ; 2-Methylthiopyridin-4(1H)-one nucleosides ; Human immunodeficiency virus ; Herpes simplex virus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Methyl-2,3-didesoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranosid (3) und 1,5-di-O-Acetyl-2,3-didesoxy-3-phthalimido-β-D-erythro-pentofuranose (12) wurden in Gegenwart von Trimethylsilyltriflat als Katalysator mit den silylierten 2-Methylthiopyridin-4(1H)-onen2a, b zu den entsprechenden Nucleosiden5–6 und13 kondensiert. Bei diesen Reaktionen tritt als Nebenreaktion eine Öffnung der endocyclischen C-O — Bindung auf, sodaß auch die acyclischen Nucleoside4a, b gebildet werden. Die 3′-Fluoronucleoside wurden mit NH3/MeOH entschützt, die 3′-Phthalimidonucleoside mit Methylamin in Ethanol. Letztere Reaktion resultierte in eine gleichzeitigen Substitution der Pyrimidineinheit unter Austausch der Methylthiogruppe. Das 2-Methylthioanalogon zu 3′-Desoxy-3′-fluorthymidin zeigt mäßige Aktivität gegen HIV-1.
    Notes: Summary Methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside (3) as well as 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimodo-β-D-erythro-pentofuranose (12) were condensed with silylated 2-methylthiopyridin-4(1H)-ones2a, b in the presence of trimethylsilyl triflate as a catalyst to produce the corresponding nucleosides5, 6, 13. In these reactions, an endocyclic cleavage of C-O in3 took place; therefore, acyclic nucleosides4a, b were also formed. All 3′-fluoro nucleosides were deprotected with NH3/MeOH; the 3′-phthalimido nucleosides were deprotected with methylamine in ethanol. The latter method resulted in a concomitant substitution reaction in the pyrimidine moiety with replacement of the methylthio group. The 2-methylthio analogue of 3′-deoxy-3′-fluorothylmidine showed moderate activity against HIV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807039
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of 5-methylisocytidine derivatives (1996)
    Springer
    Monatshefte für Chemie 127 (1996), S. 455-459 
    Details
    ISSN: 1434-4475
    Keywords: Herpes simplex virus ; Human immunodeficiency virus ; Isocytidines ; N2-alkyl-5-methyl ; Nucleosides ; convergent synthesis of ; 2-Thiouridine ; 5,S2-dimethyl
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung N2-substituierte 5-Methylisocytidin-Derivate wurden ausgehend von S2-Methyl-2-thiothymidin entweder durch direkte Substitution der Methylthiogruppe durch eine Aminogruppe und anschließende Kondensation mit 1,2,3,5-tetra-O-Acetyl-β-D-ribofuranose zum acetylierten Nucleosid oder umgekehrt durch Synthese eines acetylierten 5,S2-Dimethyl-2-thiouridins und nachfolgende Behandlung mit dem entsprechenden Amin hergestellt.
    Notes: Summary N2-Substituted 5-methylisocytidine derivatives were synthesized from S2-methyl-2-thiothymine either by direct substitution of the methylthio group by an amino group and subsequent condensation with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose to give the acetylated nucleoside or by the opposite sequence first preparing an acetylated 5,S2-dimethyl-2-thiouridine followed by treatment with the appropriate amine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00810888
    Library Location Call Number Volume/Issue/Year Availability
    BibTip Others were also interested in ...
    Paper (German National Licenses)
    Fulltext
Close ⊗
This website uses cookies and the analysis tool Matomo. More information can be found here...