Home / Articles / Huprines --- an insight into the synthesis and biological properties

Huprines --- an insight into the synthesis and biological properties

Eva Mezeiova 1, 2
Eva Mezeiova
, 
Ondrej Soukup 1, 2
Ondrej Soukup
, 
Jan Korabecny 1, 2
Jan Korabecny
1 Biomedical Research Centre, University Hospital Hradec Kralove, Hradec Kralove, Czech Republic
2 Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence in Brno, Hradec Kralove, Czech Republic
10.1070/RCR4938
Published 30 November 2019
Review , RCR4938, Volume 89, Issue 10, 999-1039
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Mezeiova E., Soukup O., Korabecny J. Huprines --- an insight into the synthesis and biological properties // Russian Chemical Reviews. 2019. Vol. 89. No. 10. pp. 999-1039.
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Mezeiova E., Soukup O., Korabecny J. Huprines --- an insight into the synthesis and biological properties // Russian Chemical Reviews. 2019. Vol. 89. No. 10. pp. 999-1039.
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TY - JOUR
DO - 10.1070/RCR4938
UR - https://rcr.colab.ws/publications/10.1070/RCR4938
TI - Huprines --- an insight into the synthesis and biological properties
T2 - Russian Chemical Reviews
AU - Mezeiova, Eva
AU - Soukup, Ondrej
AU - Korabecny, Jan
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 999-1039
IS - 10
VL - 89
ER -
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@article{2019_Mezeiova,
author = {Eva Mezeiova and Ondrej Soukup and Jan Korabecny},
title = {Huprines --- an insight into the synthesis and biological properties},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4938},
number = {10},
pages = {999--1039},
doi = {10.1070/RCR4938}
}
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Mezeiova, Eva, et al. “Huprines --- an insight into the synthesis and biological properties.” Russian Chemical Reviews, vol. 89, no. 10, Nov. 2019, pp. 999-1039. https://rcr.colab.ws/publications/10.1070/RCR4938.
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Keywords

huprine; huperzine A; tacrine; acetylcholinesterase; cholinesterase; Alzheimer's disease; prion diseases

Abstract

The overlapping of tacrine and (--)-huperzine A templates yielded a family of highly potent cholinesterase inhibitors, so-called huprines. A relatively easy access to these compounds led to the development of dozens of huprine derivatives allowing to draw structure--activity relationship mainly for acetylcholinesterase and butyrylcholinesterase enzymes, but also with application to other biological targets of interest. An extension of their pharmacological profile is commonly associated with huprine scaffold binding to some other pharmacophores that yield high-molecular-weight heterodimers. The main purpose in developing the huprine family is related to Alzheimer's disease therapy. However, these compounds are also interesting lead structures in the treatment of other disorders, such as Myasthenia gravis, African trypanosomiasis, malaria, and prion diseases. The present review provides a rationale behind the development of huprines, detailed synthetic routes leading to different classes of huprines, and a thorough discussion of their potential pharmacological applications.

The bibliography includes 174 references.

Funders

Ministry of Education, Youth and Sports of the Czech Republic
ERDF IT4N no. CZ.02.1.01/0.0/0.0/18_069/0010054
Ministry of Defence of the Czech Republic
Grant Agency of Czech Republic
20-29633J
Ministry of Healt of Czech Republic, Conceptual Development of Research Organization
00179906

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