Communication

Truncated Reverse Isoxazolidinyl Nucleosides: A New Class of Allosteric HIV-1 Reverse Transcriptase Inhibitors

  1. Prof. Roberto Romeo1,*,
  2. Dr. Salvatore V. Giofrè1,
  3. Dr. Beatrice Macchi2,
  4. Dr. Emanuela Balestrieri3,
  5. Prof. Antonio Mastino4,
  6. Pedro Merino5,
  7. Dr. Caterina Carnovale1,
  8. Prof. Giovanni Romeo1,
  9. Prof. Ugo Chiacchio6

Article first published online: 9 FEB 2012

DOI: 10.1002/cmdc.201200022

Issue

ChemMedChem

ChemMedChem

Volume 7, Issue 4, pages 565–569, April 2012

Additional Information

How to Cite

Romeo, R., Giofrè, S. V., Macchi, B., Balestrieri, E., Mastino, A., Merino, P., Carnovale, C., Romeo, G. and Chiacchio, U. (2012), Truncated Reverse Isoxazolidinyl Nucleosides: A New Class of Allosteric HIV-1 Reverse Transcriptase Inhibitors. ChemMedChem, 7: 565–569. doi: 10.1002/cmdc.201200022

Author Information

  1. 1

    Dipartimento Farmaco-Chimico, Università degli Studi di Messina, Via S. S. Annunziata, 98168 Messina (Italy)

  2. 2

    Dipartimento di Neuroscienze, Università degli Studi di Roma Tor Vergata, Via Montpellier 1, 00133 Roma (Italy)

  3. 3

    Dipartimento di Medicina Sperimentale e Scienze Biochimiche, Università degli Studi di Roma Tor Vergata, Via Montpellier 1, 00133 Roma (Italy)

  4. 4

    Dipartimento di Scienze della Vita, Università degli Studi di Messina, Salita Sperone 31, 98166 Messina, Italy

  5. 5

    Departamento de Química Orgánica, ISQCH, Universidad de Zaragoza–CSIC, Campus San Francisco, 50009 Zaragoza (Spain)

  6. 6

    Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, Viale Andrea Doria 6, 95125 Catania (Italy)

*Dipartimento Farmaco-Chimico, Università degli Studi di Messina, Via S. S. Annunziata, 98168 Messina (Italy)

Publication History

  1. Issue published online: 27 MAR 2012
  2. Article first published online: 9 FEB 2012
  3. Manuscript Received: 12 JAN 2012

Funded by

  • Italian Ministry of Education, Universities, and Research (MIUR)
  • University of Messina (Italy)
  • University of Catania (Italy)
  • Interuniversity Consortium for Innovative Methodologies and Processes for Synthesis (CINMPIS), the University of Milan–Bicocca (Italy)

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Keywords:

  • docking studies;
  • HIV-1;
  • noncompetitive inhibitors;
  • pyrimidinyl isoxazolidines;
  • reverse transcriptases
Thumbnail image of graphical abstract

Affairs of the HAART! The synthesis of HEPT-derived, truncated reverse isoxazolidinyl nucleosides (shown) is reported. These compounds represent the first examples of isoxazolidines bearing a pyrimidine scaffold at the C-3 position using a glycoside-type linkage. Biological evaluation showed that some of the derivatives act as non-nucleoside inhibitors of HIV-1 reverse transcriptase, with an efficacy comparable to that of Nevirapine but with reduced toxicity.

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