SYNTHESIS OF 2-(BETA-D-RIBOFURANOSYL)THIAZOLE-4-CARBOXAMIDE 5'-PHOSPHATE ISOSTERES

被引：9
|
作者：
ANDRES, JI [1 ]
GARCIALOPEZ, T [1 ]
DELASHERAS, FG [1 ]
MENDEZCASTRILLON, PP [1 ]
机构：
[1] INST QUIM MED, JUAN CIERVA 3, E-28006 MADRID, SPAIN
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 1986年 / 5卷 / 04期
关键词：
D O I：
10.1080/07328318608068683
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The syntheses of 5''-O-sulfamoyl and 5''-O-carbamoyl tiazofurin (9 and 12) are described. One pot reaction of 2'',3''-O-isopropylidene-tiazofurin (7) with hexabutyldistannoxane and sulfamoyl chloride gave the corresponding 5''-O-sulfamoyl ester, which was deprotected to yield 9. Compound 7 reacted with phenyl chloroformate to give the 5''-O-carbophenoxy derivative which on treatment with ammonium hydroxide followed by deisopropylidenation afforded 12. Improvements on the synthetic route to the starting tiazofurin are also reported.
引用
收藏
页码：423 / 429
页数：7
相关论文
共 50 条
  • [31] POLYAZANAPHTHYLENE NUCLEOSIDES .2. SYNTHESIS OF BETA-D-RIBOFURANOSYL DERIVATIVES OF 4-QUINAZOLONE
    STOUT, MG
    ROBINS, RK
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (01) : 89 - &
  • [32] NUCLEOSIDES FROM CARBOHYDRATE ADDUCTS OF DIAMINOMALEONITRILE - A NOVEL SYNTHESIS OF 5-AMINO-1-(BETA-D-RIBOFURANOSYL)IMIDAZOLE-4-CARBOXAMIDE AND 5-AMINO-1-(BETA-D-RIBOPYRANOSYL)IMIDAZOLE-4-CARBOXAMIDE
    FERRIS, JP
    DEVADAS, B
    HUANG, CH
    REN, WY
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (06): : 747 - 754
  • [33] SYNTHESIS OF 2-SUBSTITUTED AZINO-3-(BETA-D-RIBOFURANOSYL)-5-CARBOXYMETHYLENETHIAZOLIDIN-4-ONES
    HOHNJEC, M
    KOBE, J
    VALCAVI, U
    JAPELJ, M
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1975, 12 (05) : 909 - 912
  • [34] SPECIFIC SYNTHESIS OF 3-(BETA-D-RIBOFURANOSYL)URACIL
    HOLY, A
    JOURNAL OF CARBOHYDRATES-NUCLEOSIDES-NUCLEOTIDES, 1978, 5 (06): : 487 - 501
  • [35] 4-AMINO-1-(BETA-D-RIBOFURANOSYL)BENZIMIDAZOLE
    JENKINS, SR
    HOLLY, FW
    ROBINS, RK
    JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (04) : 910 - &
  • [36] 2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity
    Popsavin, Mirjana
    Kojic, Vesna
    Spaic, Sasa
    Svircev, Milos
    Bogdanovic, Gordana
    Jakimov, Dimitar
    Aleksic, Lidija
    Popsavin, Velimir
    TETRAHEDRON, 2014, 70 (14) : 2343 - 2350
  • [37] Synthesis, conformation analysis and biological evaluation of 2-(2,3-dideoxy-beta-D-ribofuranosyl)pyridine-4-carboxamide
    Joos, PE
    Esmans, EL
    Alderweireldt, FC
    DeBruyn, A
    Balzarini, J
    DeClercq, E
    HETEROCYCLES, 1996, 43 (02) : 287 - 304
  • [38] THE SYNTHESIS OF 5-CARBOXAMIDO-4-HYDROXY-3-(BETA-D-RIBOFURANOSYL)-THIOPHENE DERIVATIVES, ANALOGS OF PYRAZOFURIN
    HUYBRECHTS, L
    BUFFEL, D
    FREYNE, E
    HOORNAERT, G
    TETRAHEDRON, 1984, 40 (13) : 2479 - 2485
  • [39] SYNTHESIS OF THIAZOLE-4-CARBOXAMIDE ADENINE-DINUCLEOTIDE - A POWERFUL INHIBITOR OF IMP DEHYDROGENASE
    GEBEYEHU, G
    MARQUEZ, VE
    KELLEY, JA
    COONEY, DA
    JAYARAM, HN
    JOHNS, DG
    JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) : 922 - 925
  • [40] BENZIMIDAZOLE RIBONUCLEOSIDES - DESIGN, SYNTHESIS, AND ANTIVIRAL ACTIVITY OF CERTAIN 2-(ALKYLTHIO) AND 2-(BENZYLTHIO)-5,6-DICHLORO-1-(BETA-D-RIBOFURANOSYL)BENZIMIDAZOLES
    DEVIVAR, RV
    KAWASHIMA, E
    REVANKAR, GR
    BREITENBACH, JM
    KRESKE, ED
    DRACH, JC
    TOWNSEND, LB
    JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (18) : 2942 - 2949
12345