SYNTHESIS OF NOVEL ISOTHIAZOLE AND ISOTHIAZOLO[4,5-D] PYRIMIDINE ANALOGS OF THE NATURAL C-NUCLEOSIDES PYRAZOFURIN AND THE FORMYCINS

被引：9
|
作者：
BUFFEL, DK [1 ]
MEERPOEL, L [1 ]
TOPPET, SM [1 ]
HOORNAERT, GJ [1 ]
机构：
[1] KATHOLIEKE UNIV LEUVEN,DEPT SCHEIKUNDE,ORGAN SYNTH LAB,B-3001 HEVERLEE,BELGIUM
来源：
NUCLEOSIDES & NUCLEOTIDES | 1994年 / 13卷 / 1-3期
关键词：
D O I：
10.1080/15257779408013275
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 cycloaddition of tri-O-benzyl-2,5-anhydro-D-allononitrile-N-sulfide with dimethyl acetylenedicarboxylate or with dimethyl fumarate followed by DDQ oxidation was found to give the benzoyl protected dimethyl 3-beta-D-ribofuranosyl-isothiazoledicarboxylate 10. This compound was converted to C-nucleosides 7a, 8 and 9, analogues of pyrazofurin, oxoformycin B and formycin respectively. Despite their structural similarities they did show neither antiviral nor antitumor activity.
引用
收藏
页码：719 / 736
页数：18
相关论文
共 50 条
  • [21] SYNTHESIS OF DERIVATIVES OF THIAZOLO[4,5-D]PYRIMIDINE .I.
    BAKER, JA
    CHATFIELD, PV
    JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04): : 603 - +
  • [22] Synthesis and pharmacological assessment of derivatives of isoxazolo[4,5-d]pyrimidine
    Wagner, E
    Becan, L
    Nowakowska, E
    BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (01) : 265 - 272
  • [23] SYNTHESIS AND ANTIVIRAL ACTIVITY OF CERTAIN GUANOSINE ANALOGS IN THE THIAZOLO[4,5-D]PYRIMIDINE RING-SYSTEM
    KINI, GD
    ANDERSON, JD
    SANGHVI, YS
    LEWIS, AF
    SMEE, DF
    REVANKAR, GR
    ROBINS, RK
    COTTAM, HB
    JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (10) : 3006 - 3010
  • [24] C-NUCLEOSIDES - SYNTHESIS OF NOVEL RIBAVIRIN ANALOGS BY CYCLOADDITION REACTIONS OF D-ALLONONITRILE-N-SULFIDE
    BUFFEL, DK
    SIMONS, BP
    DECEUNINCK, JA
    HOORNAERT, GJ
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12): : 2165 - 2168
  • [25] Synthesis of novel pyrimido[4,5-d]pyrimidine derivatives from 5-acetyl-4-aminopyrimidines
    Alexander V. Komkov
    Mikhail А. Kozlov
    Mikhail А. Prezent
    Andrey S. Dmitrenok
    Natalya G. Kolotyrkina
    Mikhail E. Minyaev
    Igor V. Zavarzin
    Chemistry of Heterocyclic Compounds, 2022, 58 : 243 - 250
  • [26] Synthesis of novel pyrimido[4,5-d]pyrimidine derivatives from 5-acetyl-4-aminopyrimidines
    Komkov, Alexander, V
    Kozlov, Mikhail A.
    Prezent, Mikhail A.
    Dmitrenok, Andrey S.
    Kolotyrkina, Natalya G.
    Minyaev, Mikhail E.
    Zavarzin, Igor, V
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2022, 58 (4-5) : 243 - 250
  • [27] Synthesis and Pharmacological Screening of Derivatives of Isoxazolo[4,3-d]pyrimidine and Isoxazolo[4,5-d]pyrimidine
    Wagner, Edwin
    Al-Kadasi, Kamal
    Becan, Lilianna
    Sawka-Dobrowolska, Wanda
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (03) : 677 - 682
  • [28] Synthesis of thiazolo[4,5-d]pyrimidine derivatives as potential antimicrobial agents
    Habib, Nargues S.
    Solliman, Raafat
    El-Tombary, Alaa A.
    El-Hawash, Soad A.
    Shaaban, Omaima G.
    ARCHIVES OF PHARMACAL RESEARCH, 2007, 30 (12) : 1511 - 1520
  • [29] SYNTHESIS AND ANTI-HIV ACTIVITY OF 4′-MODIFIED CYCLOPENTENYL PYRIMIDINE C-NUCLEOSIDES
    Liu, Lian Jin
    Hong, Joon Hee
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2009, 28 (04): : 303 - 314
  • [30] Synthesis of thiazolo[4,5-d]pyrimidine derivatives as potential antimicrobial agents
    Nargues S. Habib
    Raafat Soliman
    Alaa A. El-Tombary
    Soad A. El-Hawash
    Omaima G. Shaaban
    Archives of Pharmacal Research, 2007, 30
12345