Semi-synthetic preparation of the rare, cytotoxic, deep-sea sourced sponge metabolites discorhabdins P and U

Tanja Grkovic; Balwinder Kaur; Victoria L Webb; Brent R Copp

doi:10.1016/j.bmcl.2005.12.081

Semi-synthetic preparation of the rare, cytotoxic, deep-sea sourced sponge metabolites discorhabdins P and U

Bioorg Med Chem Lett. 2006 Apr 1;16(7):1944-6. doi: 10.1016/j.bmcl.2005.12.081. Epub 2006 Jan 24.

Authors

Tanja Grkovic¹, Balwinder Kaur, Victoria L Webb, Brent R Copp

Affiliation

¹ Department of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand.

PMID: 16439119
DOI: 10.1016/j.bmcl.2005.12.081

Abstract

Semi-synthetic routes to the enzyme inhibitory and potently anti-proliferative marine natural products discorhabdins P and U were developed by one-step methylation reactions of discorhabdins C and B, respectively. Two novel semi-synthetic derivatives of discorhabdin U were also prepared, one of which (6) exhibited significant anti-proliferative activity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Drug Screening Assays, Antitumor
Leukemia P388 / pathology
Mice
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Porifera
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Quinones / chemical synthesis*
Quinones / chemistry
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Thiazepines / chemical synthesis*
Thiazepines / chemistry

Substances

Pyrroles
Quinones
Spiro Compounds
Thiazepines
discorhabdin P
discorhabdin U