A Palladium-Catalyzed Route to Huperzine A and Its Analogues and Their Anticholinesterase Activity

Giuseppe Campiani; Li Qiang Sun; Alan P. Kozikowski; Patricia Aagaard; Michael McKinney

doi:10.1021/jo00079a008

A Palladium-Catalyzed Route to Huperzine A and Its Analogues and Their Anticholinesterase Activity

Giuseppe Campiani, Li Qiang Sun, Alan P. Kozikowski, Patricia Aagaard, Michael McKinney

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Abstract

Huperzine A is an alkaloid isolated from Huperzia serrata (Thunb.) Trev., a Chinese club moss the extracts of which have been used in Chinese folklore medicine to treat a variety of maladies including memory disorders. Recently, this molecule has attracted widespread attention because of its possible use in the treatment of Alzheimer's disease (AD). We describe herein a palladium-catalyzed bicycloannulation route to this molecule which makes huperzine A available in 40% overall yield. The application of this methodology to seven other huperzine A analogues together with their biological activity in the inhibition of rat cortex acetylcholinesterase (AChE) is detailed herein. None of these new compounds was more potent than the parent structure as AChE inhibitors.

Original language	English (US)
Pages (from-to)	7660-7669
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	58
Issue number	27
DOIs	https://doi.org/10.1021/jo00079a008
State	Published - 1993
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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abstract = "Huperzine A is an alkaloid isolated from Huperzia serrata (Thunb.) Trev., a Chinese club moss the extracts of which have been used in Chinese folklore medicine to treat a variety of maladies including memory disorders. Recently, this molecule has attracted widespread attention because of its possible use in the treatment of Alzheimer's disease (AD). We describe herein a palladium-catalyzed bicycloannulation route to this molecule which makes huperzine A available in 40% overall yield. The application of this methodology to seven other huperzine A analogues together with their biological activity in the inhibition of rat cortex acetylcholinesterase (AChE) is detailed herein. None of these new compounds was more potent than the parent structure as AChE inhibitors.",

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T1 - A Palladium-Catalyzed Route to Huperzine A and Its Analogues and Their Anticholinesterase Activity

AU - Campiani, Giuseppe

AU - Sun, Li Qiang

AU - Kozikowski, Alan P.

AU - Aagaard, Patricia

AU - McKinney, Michael

PY - 1993

Y1 - 1993

N2 - Huperzine A is an alkaloid isolated from Huperzia serrata (Thunb.) Trev., a Chinese club moss the extracts of which have been used in Chinese folklore medicine to treat a variety of maladies including memory disorders. Recently, this molecule has attracted widespread attention because of its possible use in the treatment of Alzheimer's disease (AD). We describe herein a palladium-catalyzed bicycloannulation route to this molecule which makes huperzine A available in 40% overall yield. The application of this methodology to seven other huperzine A analogues together with their biological activity in the inhibition of rat cortex acetylcholinesterase (AChE) is detailed herein. None of these new compounds was more potent than the parent structure as AChE inhibitors.

AB - Huperzine A is an alkaloid isolated from Huperzia serrata (Thunb.) Trev., a Chinese club moss the extracts of which have been used in Chinese folklore medicine to treat a variety of maladies including memory disorders. Recently, this molecule has attracted widespread attention because of its possible use in the treatment of Alzheimer's disease (AD). We describe herein a palladium-catalyzed bicycloannulation route to this molecule which makes huperzine A available in 40% overall yield. The application of this methodology to seven other huperzine A analogues together with their biological activity in the inhibition of rat cortex acetylcholinesterase (AChE) is detailed herein. None of these new compounds was more potent than the parent structure as AChE inhibitors.

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A Palladium-Catalyzed Route to Huperzine A and Its Analogues and Their Anticholinesterase Activity

Abstract

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