Synthesis and biological evaluation of novel homochiral carbocyclic nucleosides from 1-amino-2-indanols

  • Bioorg Med Chem. 2012 Oct 1;20(19):5986-91. doi: 10.1016/j.bmc.2012.07.028.
Esteban A Ugliarolo  1 ,  Dolores Gagey ,  Beatriz Lantaño ,  Graciela Y Moltrasio ,  Rodolfo H Campos ,  Lucía V Cavallaro ,  Albertina G Moglioni
Affiliations
  • 1. Cátedra de Química Medicinal, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, (1113) Ciudad de Buenos Aires, Argentina.
PMID: 22944333 DOI: 10.1016/j.bmc.2012.07.028
Abstract

New chiral purinyl and 8-azapurinyl carbanucleoside derivatives based on indanol were synthesized from commercial available (1S,2S)-trans-1-amino-2-indanol and (1R,2R)-trans-1-amino-2-indanol using a linear methodology. The Antiviral activity and cytotoxicity of these compounds were evaluated against herpes simplex virus type 1 (HSV-1) in Vero cells, bovine viral diarrhea virus (BVDV) in Mardin-Darby bovine kidney (MDBK) cells and hepatitis B virus (HBV) in HepG2 2.2.15 cell line. Three compounds, showed an inhibition of the HBsAg levels similar to reference drug lamivudine. One chloropurinyl nucleoside, derived from the cis-1-amino-2-indanol, was cytotoxic on MDBK cells and it could be a lead for developing Anticancer agents.