Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides.
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.
Parra
Andres
A
Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Granada, Fuentenueva s/n, 18071 Granada, Spain.
Rivas
Francisco
F
Lopez
Pilar E
PE
Garcia-Granados
Andres
A
Martinez
Antonio
A
Albericio
Fernando
F
Marquez
Nieves
N
Muñoz
Eduardo
E
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
D000596:Amino Acids; D019380:Anti-HIV Agents; D010455:Peptides; D014315:Triterpenes; C412811:maslinic acid; D009828:Oleanolic Acid