New furano- and pyrrolo[2,3-d]pyrimidine nucleosides and their 5′-O-triphosphates: Synthesis and biological properties

Bicyclic furano[2,3- d ]pyrimidine ribonucleosides were synthesized by Pd(0)-and CuI-catalyzed coupling of 5-iodouridine with terminal alkynes. The treatment of the resulting nucleosides with ammonia or methylamine solution in aqueous alcohol resulted in pyrrolo-and N 7 -methylpyrrolo[2,3- d ]pyrimi...

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Published in:	Russian journal of bioorganic chemistry Vol. 34; no. 5; pp. 593 - 601
Main Authors:	Ivanov, M. A., Ivanov, A. V., Krasnitskaya, I. A., Smirnova, O. A., Karpenko, I. L., Belanov, E. F., Prasolov, V. S., Tunitskaya, V. L., Alexandrova, L. A.
Format:	Journal Article
Language:	English
Published:	Dordrecht SP MAIK Nauka/Interperiodica 2008
Subjects:	Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Bovine viral diarrhea virus Hepatitis C virus Life Sciences Organic Chemistry RNA polymerase of hepatitis C virus nucleosides RNA helicase/NTPase of hepatitis C virus hepatitis C virus furano- and pyrrolo[2,3-d]pyrimidine ribonucleosides nucleoside 5′-O-triphosphates bovine viral diarrhea virus
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Summary:	Bicyclic furano[2,3- d ]pyrimidine ribonucleosides were synthesized by Pd(0)-and CuI-catalyzed coupling of 5-iodouridine with terminal alkynes. The treatment of the resulting nucleosides with ammonia or methylamine solution in aqueous alcohol resulted in pyrrolo-and N 7 -methylpyrrolo[2,3- d ]pyrimidine nucleosides. 5′- O -Triphosphates of bicyclic nucleosides were obtained by the treatment of the nucleosides with POCl 3 in the presence of a “proton sponge.” The 5′- O -triphosphates are not substrates for HCV RNA-dependent RNA polymerase, but are effective substrates for HCV RNA helicase/NTPase and did not inhibit ATP hydrolysis. Only 3-(β- D -ribofuranosyl)-6-decyl-2,3-dihydrofuro-[2,3- d ]pyrimidin-2-one showed a moderate anti-HCV activity in the HCV replicon system and efficiently inhibited replication of bovine viral diarrhea virus (BVDV) in KCT-cells, other compounds being inactive. None of the compounds were cytotoxic within the tested range of concentrations.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1
ISSN:	1068-1620 1608-330X
DOI:	10.1134/S1068162008050099