title: Synthesis and biological evaluation of novel homochiral carbocyclic nucleosides from 1-amino-2-indanols.
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.
authors.affiliation: Cátedra de Química Medicinal, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, (1113) Ciudad de Buenos Aires, Argentina.
authors.forename: Esteban A
authors.initials: EA
authors.lastname: Ugliarolo
authors.forename: Dolores
authors.initials: D
authors.lastname: Gagey
authors.forename: Beatriz
authors.initials: B
authors.lastname: Lantaño
authors.forename: Graciela Y
authors.initials: GY
authors.lastname: Moltrasio
authors.forename: Rodolfo H
authors.initials: RH
authors.lastname: Campos
authors.forename: Lucía V
authors.initials: LV
authors.lastname: Cavallaro
authors.forename: Albertina G
authors.initials: AG
authors.lastname: Moglioni
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001912:Bovine Virus Diarrhea-Mucosal Disease / Q000188:drug therapy; D002417:Cattle; D002460:Cell Line; D002522:Chlorocebus aethiops; D001908:Diarrhea Viruses, Bovine Viral / Q000187:drug effects; D004285:Dogs; D056945:Hep G2 Cells; D006509:Hepatitis B / Q000188:drug therapy; D006515:Hepatitis B virus / Q000187:drug effects; D006561:Herpes Simplex / Q000188:drug therapy; D018259:Herpesvirus 1, Human / Q000187:drug effects; D006801:Humans; D007189:Indans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D014709:Vero Cells
chemical_list: D000998:Antiviral Agents; D007189:Indans; D009705:Nucleosides; C116915:aminoindanol