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

Authors
BUFFEL DK MEERPOEL L TOPPET SM HOORNAERT GJ
Citation
Dk. Buffel et al., SYNTHESIS OF NOVEL ISOTHIAZOLE AND ISOTHIAZOLO[4,5-D] PYRIMIDINE ANALOGS OF THE NATURAL C-NUCLEOSIDES PYRAZOFURIN AND THE FORMYCINS, Nucleosides & nucleotides, 13(1-3), 1994, pp. 719-736
Citations number
76
Categorie Soggetti
Biology
Journal title
Nucleosides & nucleotides → ACNP
ISSN journal
07328311
Volume
13
Issue
1-3
Year of publication
1994
Pages
719 - 736
Database
ISI
SICI code
0732-8311(1994)13:1-3<719:SONIAI>2.0.ZU;2-L
Abstract
The cycloaddition of tri-O-benzyl-2,5-anhydro-D-allononitrile-N-sulfid e with dimethyl acetylenedicarboxylate or with dimethyl fumarate follo wed 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, oxof ormycin B and formycin respectively. Despite their structural similari ties they did show neither antiviral nor antitumor activity.