The synthesis and biological evaluation of alkyl and benzyl naphthyridinium analogs of eupolauridine as potential antimicrobial and cytotoxic agents
Eupolauridine, an indenonaphthyridine alkaloid, has been previously reported by us to exhibit antifungal activity. This study describes the synthesis of new alkyl and benzyl naphthyridinium/pyridinium analogs of eupolauridine as potential antifungal agent
Taghavi-Moghadam, Shahriyar,Kwong, Cecil D.,Secrist, John A.,Khan, Shabana I.,Clark, Alice M.
SESQUITERPENES AND ALKALOIDS FROM CLEISTOPHOLIS PATENS
Key Word Index - Cleistopholis patens; Annonaceae; sesquiterpenes; methyl-(-)-(trans)-(trans)-10,11-dihydroxyfarnesoate; methyl-(+)-(trans)- 10-hydroxy-6,11-cyclofarnes-7(14)-enoate; aza-polycyclic alkaloids; onychine; cleistopholine; naphthyridine alkaloids; eupolauridine; eupolauridine N-oxides. The root bark of Cleistopholis patens collected in Ghana yielded two sesquiterpenes and five alkaloids.The sesquiterpenes have beencharacterised as the acyclic methyl-(-)-(trans)-(trans)-10,11-dihydroxyfarnesoate and its monocyclic derivative methyl-(+)-(trans)-10-hydroxy-6,11-cyclofarnes-7(14)-enoate.The alkaloids were of the unusual aza-polycyclic and naphthyridine groups and included one new member of both classes.Examination of stem bark samples from the same source and from Sierre Leone showed the presence of the sesquiterpenes and oxoaporphine alkaloid liriodenine but neither of the rarer alkaloid types.
Synthesis of eupolauridine and its benzo-annulated derivative
The unique diazafluoranthene alkaloid eupolauridine (1) was synthesized by a three-step routine utilizing as the initial step the thermal rearrangement of the oxime O-crotyl ether 12, which afforded onychine (2). Bracher pyridine synthesis procedure subsequently converted 2 into 1. On the other hand, Friedlander reaction was employed for the synthesis of 3, which is a benzo-annulated derivative of eupolauridine (1).
Polycyclic Aromatic Alkaloids, II: Synthesis of Onychine and Eupolauridine
The total synthesis of onychine (5) is improved by a new approach to the biaryl 4.Eupolauridine (7) is prepared from 5 in a one pot synthesis via the enamine 6.
Bracher, Franz
p. 293 - 294
(2007/10/02)
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