Effect of the Cycle Size and Spacer Structure in Tacrine and its Cyclopentyl Homologue Conjugates with 5-(4-trifluoromethyl-phenylamino)-1,2,4-thiadiazole on the Spectrum of their Biological Activity

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Published: Sep 10, 2018
DOI: https://doi.org/10.18097/BMCRM00027
Keywords:
tacrine 1,2,4-thiadiazoles acethylcholinesterase butyrylcholinesterase antioxidants

Main Article Content

N.V. Kovaleva
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
A.N. Proshin
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
E.V. Rudakova
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
N.P. Boltneva
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
I.V. Serkov
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
G.F. Makhaeva
Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia

Abstract

The conjugates of tacrine and its cyclopentyl analogue with 5-(4-trifluoromethyl-phenylamino)-1,2,4-thiadiazole, combined with two different spacers, pentylaminopropane and pentylaminopropene, were synthesized. Their esterase profile, the ability to displace propidium from the peripheral anionic site (PAS) of acetylcholinesterase (AChE) and antioxidant activity in the ABTS test were investigated. The compounds obtained effectively inhibit cholinesterases with a predominant effect on butyrylcholinesterase, displace propidium from the PAS of Electrophorus electricus AChE (EeAChE) and exhibit a high radical-scavenging capacity. It is shown that, depending on the spacer structure, particulary, the presence of a propenamine or propanamine fragment, the spectrum of biological activity of the conjugates changes.

Article Details

How to Cite
Kovaleva, N., Proshin, A., Rudakova, E., Boltneva, N., Serkov, I., & Makhaeva, G. (2018). Effect of the Cycle Size and Spacer Structure in Tacrine and its Cyclopentyl Homologue Conjugates with 5-(4-trifluoromethyl-phenylamino)-1,2,4-thiadiazole on the Spectrum of their Biological Activity. Biomedical Chemistry: Research and Methods, 1(3), e00027. https://doi.org/10.18097/BMCRM00027
Issue
Vol. 1 No. 3 (2018)
Section
EXPERIMENTAL RESEARCH

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