Versatile routes to marine sponge metabolites through benzylidene rhodanines.

Abstract

The first total synthesis of the marine natural products Psammaplin C and Tokaradine A is described. Benzylidene rhodanines were utilized as versatile intermediates toward the synthesis of seven brominated marine sponge metabolites through the optimization of protection group strategies. Spermatinamine demonstrated good inhibition of all cancer cell lines tested, in particular the leukemia K562 and colon cancer HT29 cell lines.

• Authors: Suresh K Kottakota, Mathew Benton, Dimitrios Evangelopoulos, Juan D Guzman, Sanjib Bhakta, Timothy D McHugh, Mark Gray, Paul W Groundwater, Emma C L Marrs, John D Perry, J Jonathan Harburn
• Journal: Organic letters (Org Lett) Vol. 14 Issue 24 Pg. 6310-3 (Dec 21 2012) ISSN: 1523-7052 [Electronic] United States
• PMID: 23234337 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Benzylidene Compounds
• Hydrocarbons, Brominated
• Sulfones
• psammaplin C
• spermatinamine
• tokaradine A
• Spermine
• Tyrosine
• Rhodanine

Topics

• Animals
• Benzylidene Compounds (chemical synthesis, chemistry, pharmacology)
• Drug Screening Assays, Antitumor
• HT29 Cells
• Humans
• Hydrocarbons, Brominated (chemical synthesis, chemistry, pharmacology)
• Marine Biology
• Molecular Structure
• Porifera (chemistry)
• Rhodanine (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
• Spermine (analogs & derivatives, pharmacology)
• Sulfones (chemical synthesis, chemistry, pharmacology)
• Tyrosine (analogs & derivatives, pharmacology)