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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and antiviral evaluation of quinazoline, thieno-[2,3-d]pyrimidine, and lumazine analogues of 3′-fluoro-3′-deoxythymidine (FLT) (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1371-1375 
    Details
    ISSN: 0947-3440
    Keywords: Nucleosides ; HIV ; 3′-Fluoronucleosides ; FLT analogues ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,4(1H,3H)-Quinazolinediones 3a-c, lumazine (3d) and thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (8) were silylated and condensed with methyl 2,3-dideoxy-3-fluoro-5-O-(4-phenylbenzoyl)-β-D-erythro-pentofuranoside (2) by using trimethylsilyl triflate as a catalyst to afford the corresponding cyclic nucleosides 4 and 9 and acyclic nucleosides 5 and 10. Removal of the protecting group from the glycon moiety was achieved in good yields by treatment with sodium methoxide in methanol at room temperature. The new FLT analogues were devoid of activity against HIV-1 and HSV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199507183
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of Uridine with Methylene-2-thiohydantoin as 5-Substituent (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 619-621 
    Details
    ISSN: 0170-2041
    Keywords: Uridine, methylene-2-thiohydantoin derivative ; Nucleosides ; 2-Thiohydantoin ; Herpes simplex virus ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 5-Formyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)uracil (4) was synthesized from 5-formyluracil (2) and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (3) and condensed with 2-thiohydantoin derivatives 5 by using piperidine as the catalyst to give 5-(uridin-5-ylmethylene)-2-thiohydantoin (8a) and 3-phenyl-5-(uridin-5-ylmethylene)-2-thiohydantoin (8b) after deprotection with sodium methoxide in methanol. Compound 8a was also obtained in an inversed reaction sequence from 5-formyluracil starting with condensation with 2-thiohydantoin and then with 3. The compounds 8a and 8b did not show any activity against HSV-1 or HIV-1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940613
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of α-Arabinose Nucleosides from 6-Substituted Uracils (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1-5 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Nucleosides ; Glycosides ; Uracils ; Arabinose ; Thiouracils ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of silylated 6-substituted uracils 5 with methyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside (3) in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflate) afforded a mixture of the corresponding protected N1,N3-bis(arabinofuranosyl)uracils 6 and the 6-substituted 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyluracils 8. Deprotection of 6 and 8 gave the corresponding α nucleosides 7 and 9. The reaction of silylated 6-ethyl- and 6-methylthiouracil with 3 afforded a mixture of S- and N3-glycosides 10 and 11. The glycosides 10 were deblocked by treatment with methanolic ammonia to obtain the deprotected α nucleosides 12.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930102
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    Paper (German National Licenses)
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