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

Autor: Ugliarolo EA; Cátedra de Química Medicinal, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, (1113) Ciudad de Buenos Aires, Argentina., Gagey D, Lantaño B, Moltrasio GY, Campos RH, Cavallaro LV, Moglioni AG
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2012 Oct 01; Vol. 20 (19), pp. 5986-91. Date of Electronic Publication: 2012 Jul 25.
DOI: 10.1016/j.bmc.2012.07.028
Abstrakt: 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.
(Copyright © 2012 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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