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- Title
Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues.
- Authors
Chay, Cristina I. Canché; Cansino, Rocío Gómez; Pinzón, Clara I. Espitia; Torres-Ochoa, Rubén O.; Martínez, Roberto
- 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).
- Subjects
MARINE natural products; INDOLE alkaloid synthesis; ANTITUBERCULAR agents; MYCOBACTERIUM tuberculosis; XANTHATES; SUBSTITUTION reactions; ALKALOIDS; CAULERPA
- Publication
Marine Drugs, 2014, Vol 12, Issue 4, p1757
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md12041757