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Synthesis and anti-HIV activity of new homo acyclic nucleosides, 1-(pent-4-enyl)quinoxalin-2-ones and 2-(pent-4-enyloxy)quinoxalines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A series of acyclonucleosides 6,7-disubstituted 1-(pent-4-enyl)quinoxalin-2-one derivatives and the O-analogs were synthesized by a one-step condensation of the corresponding quinoxaline bases with 5-bromo-1-pentene.The acyclonucleosides prepared were assayed against HIV-1 and HIV-2 in MT-4 cells. 6,7-Dimethyl-2-(pent-4-enyloxy)quinoxaline showed inhibition of HIV-1 with EC50 value of 0.22 ± 0.08 µg/ml and a therapeutic index of 13. This means that it was cytotoxic to MT-4 cells at CC50 of 2.6 ± 0.1 µg/ml.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt

    I. A. I. Ali

  2. College of Veterinary Medicine, University of Basrah, Basrah, Iraq

    I. A. Al-Masoudi

  3. College of Science, Department of Chemistry, University of Sulaimania, Iraq

    H. Gh. Hassan

  4. Fachbereich Chemie, Universität Konstanz, Postfach 5560, D-78457, Konstanz, Germany

    N. A. Al-Masoudi

Authors
  1. I. A. I. Ali
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  2. I. A. Al-Masoudi
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  3. H. Gh. Hassan
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  4. N. A. Al-Masoudi
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Correspondence to I. A. Al-Masoudi.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1243–1250, August, 2007.

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Ali, I.A.I., Al-Masoudi, I.A., Hassan, H.G. et al. Synthesis and anti-HIV activity of new homo acyclic nucleosides, 1-(pent-4-enyl)quinoxalin-2-ones and 2-(pent-4-enyloxy)quinoxalines. Chem Heterocycl Comp 43, 1052–1059 (2007). https://doi.org/10.1007/s10593-007-0164-0

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  • DOI: https://doi.org/10.1007/s10593-007-0164-0

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