Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues

Hrubaru, Madalina Marina; Badiceanu, Carmellina Daniela; Ekennia, Anthony Chinonso; Okafor, Sunday N.; Enache, Cristian; Tarko, Laszlo; Tecuceanu, Victorita; Maganu, Maria

Madalina Marina Hrubaru, Carmellina Daniela Badiceanu, Anthony Chinonso Ekennia, Sunday N. Okafor, Cristian Enache, Laszlo Tarko, Victorita Tecuceanu, Maria Maganu

Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues

Abstract:

Alzheimer’s is a progresive neurodegenerative disease that interferes with human cognitive ability, memory and behavior. The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes are major therapeutic routes for the treatment of Alzheimer disease. In the study, nevel bis-polymethylenquinoline-bis-carboxamides (3a-f) and bis-polymethylenquinoline-bis-carboxylic acids (5a-b) having as precursor benzidine, were obtained in good yields by Pfitzinger condensation reactions of bis-isatines with corresponding cyclanones. The compounds were characterized by elemental analysis, FT-IR, NMR and mass spectrometry. Furthermore, the compounds were subjected to molecular docking dynamics simulations to ascertain their potentials as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Molecular docking simulations showed varied binding activities towards the two binding sites of acetylcholinesterase: 4EY7 and 1OCD, and human butyrylcholinesterase: 1P0I. Compounds 3e and 5b demostrated strong binding affinities with 1P0I, 1OCD and 4EY7 biotargets similar to the binding modes of donepezil and tacrine (co-crystallized inhibitors of acetylcholinesterase) and butyrate (co-crystallized inhibitors of butyrylcholinesterase).

Keywords:
bis-tetrahydroacridin-9-carboxamides;bis-tetrahydroacridin-9-carboxylic acid; bis-polymethylenquinoline-bis-carboxamides;acetylcholinesterase inhibitors (AChEI) butyrylcholinesterase inhibitors (BChEI); Alzheimer’s disease

Issue: 2020, Volume 71, Issue 5

Pages: 163-181

Publication date: 2020/5/29

https://doi.org/10.37358/RC.20.5.8125

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This article is published under the Creative Commons Attribution 4.0 International License

Citation Styles

Cite this article as:
HRUBARU, M.M., BADICEANU, C.D., EKENNIA, A.C., OKAFOR, S.N., ENACHE, C., TARKO, L., TECUCEANU, V., MAGANU, M., Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues, Rev. Chim., 71(5), 2020, 163-181.

Vancouver
Hrubaru MM, Badiceanu CD, Ekennia AC, Okafor SN, Enache C, Tarko L, Tecuceanu V, Maganu M. Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues. Rev. Chim.[internet]. 2020 May;71(5):163-181. Available from: https://doi.org/10.37358/RC.20.5.8125

APA 6th edition
Hrubaru, M.M., Badiceanu, C.D., Ekennia, A.C., Okafor, S.N., Enache, C., Tarko, L., Tecuceanu, V. & Maganu, M. (2020). Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues. Revista de Chimie, 71(5), 163-181. https://doi.org/10.37358/RC.20.5.8125

Harvard
Hrubaru, M.M., Badiceanu, C.D., Ekennia, A.C., Okafor, S.N., Enache, C., Tarko, L., Tecuceanu, V., Maganu, M. (2020). 'Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues', Revista de Chimie, 71(5), pp. 163-181. https://doi.org/10.37358/RC.20.5.8125

IEEE
M.M. Hrubaru, C.D. Badiceanu, A.C. Ekennia, S.N. Okafor, C. Enache, L. Tarko, V. Tecuceanu, M. Maganu, "Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues". Revista de Chimie, vol. 71, no. 5, pp. 163-181, 2020. [online]. https://doi.org/10.37358/RC.20.5.8125

Text
Madalina Marina Hrubaru, Carmellina Daniela Badiceanu, Anthony Chinonso Ekennia, Sunday N. Okafor, Cristian Enache, Laszlo Tarko, Victorita Tecuceanu, Maria Maganu,
Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues,
Revista de Chimie,
Volume 71, Issue 5,
2020,
Pages 163-181,
ISSN 2668-8212,
https://doi.org/10.37358/RC.20.5.8125.
(https://revistadechimie.ro/Articles.asp?ID=8125)
Keywords: bis-tetrahydroacridin-9-carboxamides;bis-tetrahydroacridin-9-carboxylic acid; bis-polymethylenquinoline-bis-carboxamides;acetylcholinesterase inhibitors (AChEI) butyrylcholinesterase inhibitors (BChEI); Alzheimer’s disease

RIS
TY - JOUR
T1 - Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues
A1 - Hrubaru, Madalina Marina
A2 - Badiceanu, Carmellina Daniela
A3 - Ekennia, Anthony Chinonso
A4 - Okafor, Sunday N.
A5 - Enache, Cristian
A6 - Tarko, Laszlo
A7 - Tecuceanu, Victorita
A8 - Maganu, Maria
JF - Revista de Chimie
JO - Rev. Chim.
PB - Revista de Chimie SRL
SN - 2668-8212
Y1 - 2020
VL - 71
IS - 5
SP - 163
EP - 181
UR - https://doi.org/10.37358/RC.20.5.8125
KW - bis-tetrahydroacridin-9-carboxamides;bis-tetrahydroacridin-9-carboxylic acid; bis-polymethylenquinoline-bis-carboxamides;acetylcholinesterase inhibitors (AChEI) butyrylcholinesterase inhibitors (BChEI); Alzheimer’s disease
ER -

BibTex
@article{RevCh2020P163,
author = {Hrubaru Madalina Marina and Badiceanu Carmellina Daniela and Ekennia Anthony Chinonso and Okafor Sunday N. and Enache Cristian and Tarko Laszlo and Tecuceanu Victorita and Maganu Maria},
title = {Synthesis, Spectral Characterization and Molecular Docking Studies of Novel Benzidin-bis-tetrahydroacridine Analogues},
journal = {Revista de Chimie},
volume = {71},
number = {5},
pages = {163-181},
year = {2020},
issn = {2668-8212},
doi = {https://doi.org/10.37358/RC.20.5.8125},
url = {https://revistadechimie.ro/Articles.asp?ID=8125}
}

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