Synthesis and cytotoxic activity of novel 5-substituted-1-(β-L- arabinofuranosyl) pyrimidine nucleosides

Róbert Sendula, Erika Orbán, F. Hudecz, Gyula Sági, I. Jablonkai

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A series of new 5-halogeno-1-(β-L-arabinofuranosyl)uracils and their cytosine analogues were synthesized by halogenation of ara-L-uridine and ara-L-cytidine, respectively. The 5-(2-thienyl) and 5-halogenothienyl derivatives of both series were also prepared in excellent yields by Stille coupling followed by halogenation. All of these syntheses were based on benzoyl-protected derivatives. In vitro cytotoxicity experiments carried out using L1210 mouse leukemia cells showed that 5-(2-thienyl)- ara-L-uridine was the most potent compound of the new compounds; the majority of the analogues were not effective up to 200 μM concentrations.

Original languageEnglish
Pages (from-to)482-500
Number of pages19
JournalNucleosides, Nucleotides and Nucleic Acids
Volume31
Issue number6
DOIs
Publication statusPublished - Jun 1 2012

Fingerprint

Halogenation
Pyrimidine Nucleosides
Uridine
Derivatives
Leukemia L1210
Cytidine
Uracil
Cytosine
Cytotoxicity
Experiments

Keywords

  • 5-substituted pyrimidines
  • Cytotoxic activity
  • Halogenations
  • L-nucleosides

ASJC Scopus subject areas

  • Genetics
  • Biochemistry
  • Molecular Medicine

Cite this

Synthesis and cytotoxic activity of novel 5-substituted-1-(β-L- arabinofuranosyl) pyrimidine nucleosides. / Sendula, Róbert; Orbán, Erika; Hudecz, F.; Sági, Gyula; Jablonkai, I.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 31, No. 6, 01.06.2012, p. 482-500.

Research output: Contribution to journalArticle

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