SYNTHESIS AND ANTIVIRAL ACTIVITY OF 1-{[2-(PHENOXY)ETHOXY]METHYL}URACIL DERIVATIVES

Authors

  • М. С. Новиков Research Institute of Pharmacology, Volgograd State Medicinal University, Volgograd 400131
  • А. А. Озеров Research Institute of Pharmacology, Volgograd State Medicinal University, Volgograd 400131
  • Ю. А. Орлова Research Institute of Pharmacology, Volgograd State Medicinal University, Volgograd 400131
  • Р. У. Букхайт TherImmune Research Corporation, Maryland

DOI:

https://doi.org/10.1007/8301

Keywords:

1-{[2-(phenoxy)ethoxy]methyl}uracil derivatives, synthesis, anti HIV-1 activity

Abstract

The synthesis of novel 1-{[2-(phenoxy)ethoxy]methyl}uracil derivatives with different substituents in positions  and 6 of the pyrimidine ring has been carried out. It has been shown that the  alkylation  of trimethylsilyl derivatives of uracil with 2-(4-chlorophenoxy)- and 2-(4-methylphenoxy)ethoxymethyl chloride under Hilbert–Johnson reaction conditions  gives  N(1)-substitution products. It was found that the 1-{[2-(phenoxy)ethoxy]methyl}uracil derivatives show viral inhibition properties relative to  human immunodeficiency  type  1  virus in vitro. The most active compounds are 5-bromo-6-methyluracil derivatives which suppress viral reproduction by 50% at 7.2 and 7.8 micromolar concentrations.

How to Cite
Novikov, M. S.; Ozerov, A. A.; Orlova, Yu. A.; Buckheit, R. W.  Chem. Heterocycl. Compd. 2005, 41, 625. [Khim. Geterotsikl. Soedin. 2005, 726.]

For this article in the English edition, see DOI 10.1007/s10593-005-0193-5

 

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Published

2023-11-14

Issue

No. 5 (2005)

Section

Original Papers