Synthesis and biological activities of 2-pyrimidinone nucleosides. 2. 5-Halo-2-pyrimidinone 2'-deoxyribosides
- 30 June 1985
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 28 (7) , 904-910
- https://doi.org/10.1021/jm00145a010
Abstract
1-(2-Deoxy-.beta.-D-ribofuranosyl)-5-bromo-2-pyrimidinone (BrPdR) and 1-(2-deoxy-.beta.-D-ribofuranosyl)-5-iodo-2-pyrimidinone (IPdR) were synthesized by condensation of the appropriate silylated bases with 3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-.alpha.-D-ribofuranosyl chloride in 1,2-dichloroethane in the presence of SnCl4, followed by separation of the anomeric blocked nucleosides via column chromatography and subsequent deprotection with methanolic ammonia. Both BrPdR and IPdR exhibited significant antiherpes activities against various strains of HSV-1 [herpes simplex virus type 1] and HSV-2, the latter compound (IPdR) showing the higher activity as well as the stronger binding to the virus-specific thymidine kinase.This publication has 11 references indexed in Scilit:
- Nucleoside Syntheses, XXIII1) On the Mechanism of Nucleoside SynthesisEuropean Journal of Inorganic Chemistry, 1981
- Nucleoside syntheses, XXII1)Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalystsEuropean Journal of Inorganic Chemistry, 1981
- Anti-herpes simplex virus and anti-human cell growth activity of E-5-propenyl-2'-deoxyuridine and the concept of selective protection in antivirus chemotherapyAntimicrobial Agents and Chemotherapy, 1980
- Induction of thymidine kinase and DNase in varicella-zoster virus-infected cells and kinetic properties of the virus-induced thymidine kinaseJournal of Virology, 1979
- Synthesis of 5‐methylmercaptopyrimidine nucleosidesJournal of Heterocyclic Chemistry, 1979
- Induction of deoxycytidine deaminase activity in mammalian cell lines by infection with herpes simplex virus type 1.Proceedings of the National Academy of Sciences, 1977
- Deoxythymidine kinase induced in HeLa TK- cells by herpes simplex virus type I and type II. II. Purification and characterization.Journal of Biological Chemistry, 1976
- Human deoxythymidine kinase. I. Purification and general properties of the cytoplasmic and mitochondrial isozymes derived from blast cells of acute myelocytic leukemia.Journal of Biological Chemistry, 1976
- FLUORINATED PYRIMIDINES .26. MAMMALIAN THYMIDYLATE SYNTHETASE - ITS MECHANISM OF ACTION AND INHIBITION BY FLUORINATED NUCLEOTIDES1965
- Synthesis of pyrimidin-2-one deoxyribosides and their ability to support the growth of the deoxyriboside-requiring organism Lactobacillus acidophilus R26Biochemical Journal, 1964