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Publication Type
Conference Proceedings
Author, Analytic
Morris, Andrew L.; Hepburn, S. A.; Townsend, Norman. O.; Jackson, Yvette A.
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Paper/Section Title
Approaches toward the Synthesis of Nitrogenous Analogues of Rotenoids.
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Proceedings Title
237th American Chemical Society National Conference
Date of Meeting
March, 2009.
Place of Meeting
Salt Lake City, Utah, USA.
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Date of Publication
2009
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Abstract
Rotenoids, of which rotenone 1 is the most popular member, possess ichthyotoxic properties valued in wildlife conservation. This class of compounds is, however, best known for their insecticidal properties. Antiviral, antifeedant and antimicrobial activities are also known. The intact A/B/C/D ring system, chromano[3,4-b]chromone 2, has been found to be vital for the expressed activity of the rotenoids. The synthesis of the 5-thio-analogues of these interesting compounds has been reported, as well as a single published result of an azarotenoid. The reported aza-analogue also contained a 6-oxo group, making it a member of another class of compounds - azarotenonoids. The 6-oxo-derivatives of the rotenoids, the rotenonoids, have been found co-occurring with the rotenoids. To the best of our knowledge no other nitrogen-containing analogues including a 7-aza or a 5, 7-diazarotenoids have been synthesized. Our research group is interested in the efficient syntheses of these nitrogen analogues. Success at this would allow for structure-activity relationship (SAR) studies of rotenoids, 5-thio-, 5-aza- (3) and 5, 7-diazarotenoids (4). Our attempts at synthesis of these novel compounds will be discussed.....
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