Synthesis of 2',3'-dideoxy-3'-C-(hydroxymethyl)-4'-thiopentofuranosyl nucleosides as potential antiviral agent

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 8, 1999, Pages 1113-1114

  Ichikawa, Eiko ^a   Yamamura, Shosuke ^a   Kato, Kuniki ^b  

^a KEIO UNIVERSITY   (Japan)

^b NIPPON KAYAKU CO LTD   (Japan)

Author keywords

Antivirals; Nucleosides

Indexed keywords

5 (2 BROMOVINYL) 1 [2',3' DIDEOXY 3' C (HYDROXYMETHYL) BETA DEXTRO 4' THIOPENTOFURANOSYL]URACIL; ACRYLIC ACID METHYL ESTER; ANTIVIRUS AGENT; PALLADIUM; TARTARIC ACID; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS;

ANTIVIRAL AGENTS; MODELS, CHEMICAL; NUCLEOSIDES;

EID: 0033583469     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00142-0     Document Type: Article

References (8)

1. Maudgal, P. C; De Clercq, E.; Missotten, L. Antiviral Res. 1984, 4, 281-291.
2. Michael, R. D.; Paul. L. C.; Richard, T. W. J. Med. Chem. 1991, 34, 2782-2786.
3. Two groups have reported the synthesis of the same type of compound 3 that we have prepared, though their routes to these compounds are different from ours. Brånalt, J.; Kvarnström, I.; Niklasson, G.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994,59, 1783-1788. Brånalt, J.; Kvarnström, L; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994, 59, 4430-4432. Mann, J.; Tench, A.; J.; Weymouth-Wilson, A. C.; Shaw-Ponter, S.; Young, R. J. J. Chem. Soc. Perkin Trans I. 1995, 677-681.
4. Two groups have reported the synthesis of the same type of compound 3 that we have prepared, though their routes to these compounds are different from ours. Brånalt, J.; Kvarnström, I.; Niklasson, G.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994,59, 1783-1788. Brånalt, J.; Kvarnström, L; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994, 59, 4430-4432. Mann, J.; Tench, A.; J.; Weymouth-Wilson, A. C.; Shaw-Ponter, S.; Young, R. J. J. Chem. Soc. Perkin Trans I. 1995, 677-681.
5. Two groups have reported the synthesis of the same type of compound 3 that we have prepared, though their routes to these compounds are different from ours. Brånalt, J.; Kvarnström, I.; Niklasson, G.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994,59, 1783-1788. Brånalt, J.; Kvarnström, L; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994, 59, 4430-4432. Mann, J.; Tench, A.; J.; Weymouth-Wilson, A. C.; Shaw-Ponter, S.; Young, R. J. J. Chem. Soc. Perkin Trans I. 1995, 677-681.
6. Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4245-4248.
7. Heck, R. F. Org. React. 1982, 17, 345-390.
8. Evaluation of compound 4 against HSV-1 and HSV-2 in Vero cells by a plaque reduction assay at concentrations up to 10 μg/ml, and HIV-1 in MT-4 cells by an indirect immunofluorescence assay at concentrations up to 100 μg/ml revealed this compound to be devoid of antiviral activity and cytotoxicity.