Biomimetic synthesis and biological evaluation of Aplidiopsamine A.

Panarese JD, Lindsley CW
Org Lett. 2012 14 (22): 5808-10

PMID: 23106227 · PMCID: PMC3500438 · DOI:10.1021/ol3024665

The first total synthesis of Aplidiopsamine A, a rare 3H-pyrrolo[2,3-c]quinoline alkaloid from the Aplidiopsis confluata, has been achieved following the proposed biosynthesis. This biomimetic synthesis requires only five steps and proceeds in 20.8% overall yield. Biological evaluation across large panels of discrete molecular targets identified that Aplidiopsamine A is a highly selective PDE4 inhibitor, a target for numerous CNS disorders.

MeSH Terms (11)

Alkaloids Animals Australia Brain Diseases Molecular Structure Phosphodiesterase 4 Inhibitors Pyrroles Quinolines Stereoisomerism Structure-Activity Relationship Urochordata

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