78692-74-7Relevant academic research and scientific papers
Synthesis and biological evaluation of carbon-11-labeled acyclic and furo[2,3-d]pyrimidine derivatives of bicyclic nucleoside analogues (BCNAs) for structure-brain uptake relationship study of BCNA tracers
Chitneni, Satish K.,Balzarini, Jan,Celen, Sofie,Dyubankova, Natalia,Verbruggen, Alfons M.,Bormans, Guy M.
, p. 159 - 166 (2008/09/19)
We reported earlier on radiolabeled alkoxyphenyl bicyclic nucleoside analogues (BCNAs) as potential positron emission tomography (PET) reporter probes for imaging of varicella zoster virus thymidine kinase (VZV-tk) gene in vivo. Despite their favorable ph
Inhibition of hepatitis B virus (HBV) replication by pyrimidines bearing an acyclic moiety: Effect on wild-type and mutant HBV
Semaine, Wassila,Johar, Monika,Tyrrell, D. Lorne J.,Kumar, Rakesh,Agrawal
, p. 2049 - 2054 (2007/10/03)
Chronic hepatitis B virus (HBV) infection remains a major health problem worldwide. The main clinical limitation of a current antiviral drug for HBV, lamivudine, is the emergence of drug-resistant viral strains upon prolonged therapy. A group of 5-, 6-, or 5,6-substituted acyclic pyrimidine nucleosides with a 1-[(2-hydroxyethoxy)methyl] moiety were synthesized and evaluated for antiviral activities. The target compounds were prepared by the reaction of silylated uracils possessing a variety of substituents at the C-5 or C-6 positions or both with 1,3-dioxolane in the presence of potassium iodide and chlorotrimethylsilane by a convenient and single-step synthesis. Among the compounds tested, 5-chloro and 5-bromo analogues possessing an acyclic glycosyl moiety were the most effective and selective antiviral agents in the in vitro assays against wild-type duck HBV (EC50 = 0.4-2.2 and 3.7-18.5 μM, respectively) and human HBV-containing 2.2.15 cells (EC50 = 4.5-45.4 and 18.5-37.7 μM, respectively). These compounds were also found to retain sensitivity against lamivudine-resistant HBV containing a single mutation (M204I) and double mutations (L180M/M204V). The compounds investigated did not show cytotoxicity to host HepG2 and Vero cells, up to the highest concentration tested. The results presented here confirm and accentuate the potential of acyclic pyrimidine nucleosides as anti-HBV agents and extend our previous observations. We herein report the capability of acyclic pyrimidine nucleosides to inhibit the replication of both wild-type and drug-resistant mutant HBV.
A convenient one-pot synthesis of acyclonucleosides
Ubasawa,Takashima,Sekiya
, p. 142 - 143 (2007/10/02)
Bis(trimethylsilyl)pyrimidine bases were treated directly with 1,3-dioxolane (or 2-methyl-1,3-dioxolane), chlorotrimethylsilane and a metal iodide, such as KI or NaI, in acetonitrile at room temperature to afford acyclopyrimidine derivatives, including 2-thiopyrimidine derivatives, in good yields. Introduction of an acyclic chain into 2-thiopyrimidine bases, however, necessitated the use of 2 eq of the reagents.
Synthesis of aliphatic nucleoside analogues with potential antiviral activity
Colla,Busson,De Clercq,Vanderhaeghe
, p. 569 - 576 (2007/10/02)
The synthesis of a series of double-modified adenosine and 8-aza-adenosine analogues, altered in the 6-position of the base and having the sugar moiety replaced by an acyclic hydroxylated side chain is described. Also, some aliphatic derivatives of 5-iodo- and E-5-(2-bromovinyl)uracil were prepared. Of all these compounds, only 6-hydroxylamino-9-(2,3-dihydroxypropyl)purine displayed some antiviral activity when tested in primary rabbit kidney cell cultures against vesicular stomatitis, vaccinia or herpes simplex virus.
Pyrimidine Acyclic Nucleosides. 1-pyrimidines as Candidate Antivirals
Kelley, James L.,Kelsey, John E.,Hall, William R.,Krochmal, Mark P.,Schaeffer, Howard J.
, p. 753 - 756 (2007/10/02)
A number of pyrimidine acyclic nucleosides were synthesized and tested for activity against herpes simplex virus type 1.Synthesis of 1-cytosine (8) and 1-uracil (14) was accomplished in two or three steps
