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New Emivirine (MKC-442) Analogues Containing a Tetrahydronaphthalene at C-6 and their Anti-HIV Activity

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Summary.

An 5-ethyl-2-thiouracil derivative with a 6-(tetrahydronaphthalen-1-yl)methyl substituent was synthesized by condensation of thiourea with an adequate β-ketoester which in turn was synthesized in a single step from (tetrahydronaphthalen-1-yl)acetonitrile. The latter starting material was also used to synthesize an analogously substituted tetrahydronaphthalen-1-yl substituted uracil with a locked conformation. Only the non-nucleoside derivatives prepared from the desulfurized substituted 2-thiouracil showed moderate activity against HIV whereas a corresponding non-nucleoside derivative was devoid of activity against HIV.

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Authors and Affiliations

  1. Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Odense M, Denmark

    Frans Therkelsen, Per T. Jørgensen & Erik B. Pedersen

  2. Retrovirus Laboratory, Department of Virology, State Serum Institute, Copenhagen, Denmark

    Claus Nielsen

Authors
  1. Frans Therkelsen
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  2. Per T. Jørgensen
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  3. Claus Nielsen
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  4. Erik B. Pedersen
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Corresponding author

Correspondence to Erik B. Pedersen.

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Therkelsen, F., Jørgensen, P., Nielsen, C. et al. New Emivirine (MKC-442) Analogues Containing a Tetrahydronaphthalene at C-6 and their Anti-HIV Activity. Monatsh. Chem. 138, 495–503 (2007). https://doi.org/10.1007/s00706-007-0598-1

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  • DOI: https://doi.org/10.1007/s00706-007-0598-1

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