113366-10-2Relevant academic research and scientific papers
Semisynthesis and antiplasmodial activity of the quinoline alkaloid aurachin E
Hoefle, Gerhard,Boehlendorf, Bettina,Fecker, Thomas,Sasse, Florenz,Kunze, Brigitte
, p. 1967 - 1969 (2008)
A one-step synthesis of the rare aurachin E (1) from the easily accessible aurachin C (2) and cyanogen bromide is described. 3-Bromocarbamoylquinoline (5) is formed in a side reaction with concomitant loss of the 3-farnesyl residue. In an alternative approach, aurachin D (3) was reacted with phosgene and sodium azide to form the imidazolone ring of 1 via n-acylation. Unexpectedly, the initial reaction occurred at the carbonyl group of 3 to give 1H-pyrrolo[3,2-c]quinoline 4. The reaction sequence represents a novel route to this type of compound. Aurachin E, contrary to other aurachins, combines a high in vitro antiplasmodial activity with low cytotoxicity and absence of mitochondrial respiratory inhibition.
