New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors

Pelayo Camps; Joan Contreras; Rachid El Achab; Jordi Morral; Diego Muñoz-Torrero; Mercè Font-Bardia; Xavier Solans; Albert Badia; Nuria M. Vivas

doi:10.1016/S0040-4020(00)00363-X

New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors

Pelayo Camps, Joan Contreras, Rachid El Achab, Jordi Morral, Diego Muñoz-Torrero, Mercè Font-Bardia, Xavier Solans, Albert Badia, Nuria M. Vivas

Department of Pharmacology, Therapeutics and Toxicology

Research output: Contribution to journal › Article › Research › peer-review

16 Citations (Scopus)

Abstract

rac-Huperzine A, its rac-7-ethyl-derivative and two regioisomeric analogue have been prepared though synthetic sequences involving the elaboration of the pyridisne ring in a late stage, by reaction of an intermidiate pyrrolidine enamine with propiolamide, which gave mixtures of regioisomeric pyridone derivatives. The acetylcholinesterase inhibitory activity of these and two other recently described 11-unsubstituted huperzine A analogues was determined, the rac-7-ethyl analogue of huperzine A being the most active compound, although it is about 12-fold less active than (-)- huperzine A. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	4541-4553
Journal	Tetrahedron
Volume	56
Issue number	26
DOIs	https://doi.org/10.1016/S0040-4020(00)00363-X
Publication status	Published - 23 Jun 2000

Keywords

Acetylcholinesterase inhibitory activity
Biologically active compounds
Polycyclic heterocyclic compounds
Pyridones

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10.1016/S0040-4020(00)00363-X

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title = "New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors",

abstract = "rac-Huperzine A, its rac-7-ethyl-derivative and two regioisomeric analogue have been prepared though synthetic sequences involving the elaboration of the pyridisne ring in a late stage, by reaction of an intermidiate pyrrolidine enamine with propiolamide, which gave mixtures of regioisomeric pyridone derivatives. The acetylcholinesterase inhibitory activity of these and two other recently described 11-unsubstituted huperzine A analogues was determined, the rac-7-ethyl analogue of huperzine A being the most active compound, although it is about 12-fold less active than (-)- huperzine A. (C) 2000 Elsevier Science Ltd.",

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author = "Pelayo Camps and Joan Contreras and {El Achab}, Rachid and Jordi Morral and Diego Mu{\~n}oz-Torrero and Merc{\`e} Font-Bardia and Xavier Solans and Albert Badia and Vivas, {Nuria M.}",

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month = jun,

day = "23",

doi = "10.1016/S0040-4020(00)00363-X",

language = "English",

volume = "56",

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TY - JOUR

T1 - New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors

AU - Camps, Pelayo

AU - Contreras, Joan

AU - El Achab, Rachid

AU - Morral, Jordi

AU - Muñoz-Torrero, Diego

AU - Font-Bardia, Mercè

AU - Solans, Xavier

AU - Badia, Albert

AU - Vivas, Nuria M.

PY - 2000/6/23

Y1 - 2000/6/23

N2 - rac-Huperzine A, its rac-7-ethyl-derivative and two regioisomeric analogue have been prepared though synthetic sequences involving the elaboration of the pyridisne ring in a late stage, by reaction of an intermidiate pyrrolidine enamine with propiolamide, which gave mixtures of regioisomeric pyridone derivatives. The acetylcholinesterase inhibitory activity of these and two other recently described 11-unsubstituted huperzine A analogues was determined, the rac-7-ethyl analogue of huperzine A being the most active compound, although it is about 12-fold less active than (-)- huperzine A. (C) 2000 Elsevier Science Ltd.

AB - rac-Huperzine A, its rac-7-ethyl-derivative and two regioisomeric analogue have been prepared though synthetic sequences involving the elaboration of the pyridisne ring in a late stage, by reaction of an intermidiate pyrrolidine enamine with propiolamide, which gave mixtures of regioisomeric pyridone derivatives. The acetylcholinesterase inhibitory activity of these and two other recently described 11-unsubstituted huperzine A analogues was determined, the rac-7-ethyl analogue of huperzine A being the most active compound, although it is about 12-fold less active than (-)- huperzine A. (C) 2000 Elsevier Science Ltd.

KW - Acetylcholinesterase inhibitory activity

KW - Biologically active compounds

KW - Polycyclic heterocyclic compounds

KW - Pyridones

U2 - 10.1016/S0040-4020(00)00363-X

DO - 10.1016/S0040-4020(00)00363-X

M3 - Article

SN - 0040-4020

VL - 56

SP - 4541

EP - 4553

JO - Tetrahedron

JF - Tetrahedron

IS - 26

ER -

New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors

Abstract

Keywords

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