Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 17, Issue 3, Pages 1139-1145Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2008.12.041
Keywords
Maslinic acid; Triterpenes; Solid-phase synthesis; Anti-HIV; Peptides
Funding
- Comision Interministerial de Ciencia y Tecnologia
- Ministerio de Educacion y Cultura
- Junta de Andalucia [P06-CTS-01353]
- 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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