Synthesis and biological activities of N-(3-Carboxylpropyl)-5-amino-2- hydroxy-3-tridecyl-1,4-benzoquinone and analogues

Manikandadas M. Madathil, Omar Khdour, Jennifer Jaruvangsanti, Sidney Hecht

Research output: Contribution to journalArticle

2 Scopus citations


The synthesis of benzoquinone natural product 2 and three analogues is described. The synthesized compounds were tested for their ability to protect Friedreich's ataxia (FRDA) lymphocytes from induced oxidative stress. One of the analogues (3) conferred cytoprotection in a dose-dependent manner in FRDA lymphocytes at micromolar concentrations. The biological assays suggest that the modification of the 2-hydroxy and N-(3-carboxypropyl) groups in the natural product can improve its antioxidant activity and significantly enhance its ability to protect mitochondrial function under conditions of oxidative stress.

Original languageEnglish (US)
Pages (from-to)2209-2215
Number of pages7
JournalJournal of Natural Products
Issue number12
StatePublished - Dec 28 2012


ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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