Synthesis and neuroprotective activity of 3-aryl-3-azetidinyl acetic acid methyl ester derivatives

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F23%3A00578898" target="_blank" >RIV/61389030:_____/23:00578898 - isvavai.cz</a>
Alternative codes found
RIV/00216275:25310/23:39920494 RIV/00098892:_____/23:10158392 RIV/61989592:15310/23:73620295 RIV/61989592:15110/23:73620295
Result on the web
<a href="https://doi.org/10.1002/ardp.202300378" target="_blank" >https://doi.org/10.1002/ardp.202300378</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ardp.202300378" target="_blank" >10.1002/ardp.202300378</a>

Result language
angličtina
Original language name
Synthesis and neuroprotective activity of 3-aryl-3-azetidinyl acetic acid methyl ester derivatives
Original language description
A library of 3-aryl-3-azetidinyl acetic acid methyl ester derivatives was prepared from N-Boc-3-azetidinone employing the Horner-Wadsworth-Emmons reaction, rhodium(I)-catalyzed conjugate addition of arylboronic acids, and subsequent elaborations to obtain N-unprotected hydrochlorides, N-alkylated and N-acylated azetidine derivatives. The compounds were evaluated for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity, revealing several derivatives to possess AChE inhibition comparable to that of the AChE inhibitor rivastigmine. The binding mode of the AChE inhibitor donepezil and selected active compounds 26 and 27 within the active site of AChE was studied using molecular docking. Furthermore, the neuroprotective activity of the prepared compounds was evaluated in models associated with Parkinson's disease (salsolinol-induced) and aspects of Alzheimer's disease (glutamate-induced oxidative damage). Compound 28 showed the highest neuroprotective effect in both salsolinol- and glutamate-induced neurodegeneration models, and its protective effect in the glutamate model was revealed to be driven by a reduction in oxidative stress and caspase-3/7 activity.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10608 - Biochemistry and molecular biology

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2023
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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