Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues
| Autor: | Rocío Gómez Cansino, Roberto Martinez, Cristina I. Canché Chay, Clara Ines Espitia Pinzon, Rubén O. Torres-Ochoa |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Indoles
synthesis Stereochemistry Antitubercular Agents Pharmaceutical Science caulerpin analogues anti-tuberculosis activity Electrophilic aromatic substitution Article Mycobacterium tuberculosis chemistry.chemical_compound Inhibitory Concentration 50 Drug Discovery Organic chemistry Caulerpa lcsh:QH301-705.5 Pharmacology Toxicology and Pharmaceutics (miscellaneous) IC50 Biological Products Natural product biology Alkaloid biology.organism_classification lcsh:Biology (General) chemistry Yield (chemistry) Xanthate |
| Zdroj: | Marine Drugs Marine Drugs, Vol 12, Iss 4, Pp 1757-1772 (2014) Marine Drugs; Volume 12; Issue 4; Pages: 1757-1772 |
| ISSN: | 1660-3397 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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