☆ 4.7 Article

Solution- and solid-phase synthesis and anti-HIV activity of maslinic acid derivatives containing amino acids and peptides

BIOORGANIC & MEDICINAL CHEMISTRY (2009)

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期刊

BIOORGANIC & MEDICINAL CHEMISTRY
卷 17, 期 3, 页码 1139-1145

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2008.12.041

关键词

Maslinic acid; Triterpenes; Solid-phase synthesis; Anti-HIV; Peptides

类别

Biochemistry & Molecular Biology Chemistry, Medicinal Chemistry, Organic

资金

  1. Comision Interministerial de Ciencia y Tecnologia
  2. Ministerio de Educacion y Cultura
  3. Junta de Andalucia [P06-CTS-01353]
  4. Spanish RIS Network 'Red de Investigacion en SIDA' [RD06-0006]

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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. (C) 2009 Published by Elsevier Ltd.

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