Synthesis and anti-tuberculosis activity of the marine natural product caulerpin and its analogues.

Abstract

Caulerpin (1a), a bis-indole alkaloid from the marine algal Caulerpa sp., was synthesized in three reaction steps with an overall yield of 11%. The caulerpin analogues (1b-1g) were prepared using the same synthetic pathway with overall yields between 3% and 8%. The key reaction involved a radical oxidative aromatic substitution involving xanthate (3) and 3-formylindole compounds (4a-4g). All bis-indole compounds synthesized were evaluated against the Mycobacterium tuberculosis strain H37Rv, and 1a was found to display excellent activity (IC₅₀ 0.24 µM).

• Authors: Cristina I Canché Chay, Rocío Gómez Cansino, Clara I Espitia Pinzón, Rubén O Torres-Ochoa, Roberto Martínez
• Journal: Marine drugs (Mar Drugs) Vol. 12 Issue 4 Pg. 1757-72 (Mar 27 2014) ISSN: 1660-3397 [Electronic] Switzerland
• PMID: 24681629 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antitubercular Agents
• Biological Products
• Indoles
• caulerpin

Topics

• Antitubercular Agents (chemical synthesis, chemistry, pharmacology)
• Biological Products (chemical synthesis, chemistry, pharmacology)
• Caulerpa (chemistry)
• Indoles (chemical synthesis, chemistry, pharmacology)
• Inhibitory Concentration 50
• Mycobacterium tuberculosis (drug effects)