title: Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides.
abstract: Maslinic acid (1) has been coupled at C-28 with several alpha- and omega-amino acids by using solution- and solid-phase synthetic procedures. Twelve derivatives (2-13) with a single amino acid residue were prepared in solution phase, whereas a dipeptide (14), a tripeptide (15), and a series of conjugate dipeptides (16-24) were synthesized in solid phase. The anti-HIV activity of these compounds was assessed on MT-2 cells infected with viral clones carrying the luciferase gene as a reporter. While in maslinic acid (1) were present both cytotoxic and antiviral activities, only the derivatives 13 and 24 showed anti-HIV-1 activity and therefore represent a novel class of anti-HIV-1 compounds.
authors.affiliation: Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Granada, Fuentenueva s/n, 18071 Granada, Spain.
authors.forename: Andres
authors.initials: A
authors.lastname: Parra
authors.forename: Francisco
authors.initials: F
authors.lastname: Rivas
authors.forename: Pilar E
authors.initials: PE
authors.lastname: Lopez
authors.forename: Andres
authors.initials: A
authors.lastname: Garcia-Granados
authors.forename: Antonio
authors.initials: A
authors.lastname: Martinez
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
authors.forename: Nieves
authors.initials: N
authors.lastname: Marquez
authors.forename: Eduardo
authors.initials: E
authors.lastname: Muñoz
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D006801:Humans; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D009828:Oleanolic Acid / Q000031:analogs & derivatives
chemical_list: D000596:Amino Acids; D019380:Anti-HIV Agents; D010455:Peptides; D014315:Triterpenes; C412811:maslinic acid; D009828:Oleanolic Acid