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Novel conjugates of 4-amino-2,3-polymethylenequinolines and vanillin as potential multitarget agents for AD treatment

Galina Faivelevna Makhaeva 1
Galina Faivelevna Makhaeva
, 
Igor Viktorovich Serkov 1
Igor Viktorovich Serkov
, 
Nadezhda Vladimirovna Kovaleva 1
Nadezhda Vladimirovna Kovaleva
, 
Elena Vladimirovna Rudakova 1
Elena Vladimirovna Rudakova
, 
Natalia Pavlovna Boltneva 1
Natalia Pavlovna Boltneva
, 
Ekaterina A Kochetkova 2
Ekaterina A Kochetkova
, 
Alexey N Proshin 1
Alexey N Proshin
, 
Sergei Olegovich Bachurin 1
Sergei Olegovich Bachurin
10.1016/j.mencom.2021.09.005
Published 2021-09-08
Communication , Volume 31, Issue 5, 606-608
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Makhaeva G. F. et al. Novel conjugates of 4-amino-2,3-polymethylenequinolines and vanillin as potential multitarget agents for AD treatment // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 606-608.
GOST all authors (up to 50) Copy
Makhaeva G. F., Serkov I. V., Kovaleva N. V., Rudakova E. V., Boltneva N. P., Kochetkova E. A., Proshin A. N., Bachurin S. O. Novel conjugates of 4-amino-2,3-polymethylenequinolines and vanillin as potential multitarget agents for AD treatment // Mendeleev Communications. 2021. Vol. 31. No. 5. pp. 606-608.
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TY - JOUR
DO - 10.1016/j.mencom.2021.09.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.005
TI - Novel conjugates of 4-amino-2,3-polymethylenequinolines and vanillin as potential multitarget agents for AD treatment
T2 - Mendeleev Communications
AU - Makhaeva, Galina Faivelevna
AU - Serkov, Igor Viktorovich
AU - Kovaleva, Nadezhda Vladimirovna
AU - Rudakova, Elena Vladimirovna
AU - Boltneva, Natalia Pavlovna
AU - Kochetkova, Ekaterina A
AU - Proshin, Alexey N
AU - Bachurin, Sergei Olegovich
PY - 2021
DA - 2021/09/08
PB - Mendeleev Communications
SP - 606-608
IS - 5
VL - 31
ER -
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@article{2021_Makhaeva,
author = {Galina Faivelevna Makhaeva and Igor Viktorovich Serkov and Nadezhda Vladimirovna Kovaleva and Elena Vladimirovna Rudakova and Natalia Pavlovna Boltneva and Ekaterina A Kochetkova and Alexey N Proshin and Sergei Olegovich Bachurin},
title = {Novel conjugates of 4-amino-2,3-polymethylenequinolines and vanillin as potential multitarget agents for AD treatment},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.005},
number = {5},
pages = {606--608},
doi = {10.1016/j.mencom.2021.09.005}
}
MLA
Cite this
MLA Copy
Makhaeva, Galina Faivelevna, et al. “Novel conjugates of 4-amino-2,3-polymethylenequinolines and vanillin as potential multitarget agents for AD treatment.” Mendeleev Communications, vol. 31, no. 5, Sep. 2021, pp. 606-608. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.09.005.

Abstract

A series of novel conjugates of 4-amino-2,3-polymethylene quinolines and phenolic antioxidant vanillin was synthesized by the condensation of aminoquinolines with vanillin followed by reduction of imines with sodium borohydride. The conjugates effectively inhibit AChE and BChE with preferable BChE inhibition and displace propidium from the PAS AChE. Compounds with aminoalkyl spacer have preferable esterase profile being more potent cholinesterases inhibitors with lower anti-CES activity and are the most potent antioxidants in ABTS and FRAP tests.

References

1.
World Alzheimer Report 2019: Attitudes to Dementia, Alzheimer’s Disease International, London, 2019, https://www.alz.co.uk/research/ world-report-2019.
2.
Drugs in Clinical Trials for Alzheimer's Disease: The Major Trends
Bachurin S.O., Bovina E.V., Ustyugov A.A.
Medicinal Research Reviews, 2017
3.
10.1016/j.mencom.2021.09.005_b0015
Oset-Gasque
Neurosci., 2018
4.
10.1016/j.mencom.2021.09.005_b0020
Martinez
Drugs, 2006
5.
Butyrylcholinesterase inhibitors ameliorate cognitive dysfunction induced by amyloid-β peptide in mice
Furukawa-Hibi Y., Alkam T., Nitta A., Matsuyama A., Mizoguchi H., Suzuki K., Moussaoui S., Yu Q., Greig N.H., Nagai T., Yamada K.
Behavioural Brain Research, 2011
6.
Nordberg A., Ballard C., Bullock R., Darreh-Shori T., Somogyi M.
The primary care companion for CNS disorders, 2013
7.
Targeting acetylcholinesterase and butyrylcholinesterase in dementia
Lane R.M., Potkin S.G., Enz A.
International Journal of Neuropsychopharmacology, 2005
8.
Neuroprotective and Cognition-Enhancing Properties of MK-801 Flexible Analogs
BACHURIN S., TKACHENKO S., BASKIN I., LERMONTOVA N., MUKHINA T., PETROVA L., USTINOV A., PROSHIN A., GRIGORIEV V., LUKOYANOV N., PALYULIN V., ZEFIROV N.
Annals of the New York Academy of Sciences, 2006
9.
Structural Basis for Understanding Structure−Activity Relationships for the Glutamate Binding Site of the NMDA Receptor
Tikhonova I.G., Baskin I.I., Palyulin V.A., Zefirov N.S., Bachurin S.O.
Journal of Medicinal Chemistry, 2002
10.
Multi-target-Directed Ligands To Combat Neurodegenerative Diseases
Cavalli A., Bolognesi M.L., Minarini A., Rosini M., Tumiatti V., Recanatini M., Melchiorre C.
Journal of Medicinal Chemistry, 2008
11.
Multitarget Drug Discovery and Polypharmacology
Bolognesi M.L., Cavalli A.
ChemMedChem, 2016
12.
Rational Design of Multitarget-Directed Ligands: Strategies and Emerging Paradigms.
Zhou J., Jiang X., He S., Jiang H., Feng F., Liu W., Qu W., Sun H.
Journal of Medicinal Chemistry, 2019
13.
Multitarget compounds bearing tacrine- and donepezil-like structural and functional motifs for the potential treatment of Alzheimer's disease
Ismaili L., Refouvelet B., Benchekroun M., Brogi S., Brindisi M., Gemma S., Campiani G., Filipic S., Agbaba D., Esteban G., Unzeta M., Nikolic K., Butini S., Marco-Contelles J.
Progress in Neurobiology, 2017
14.
Multitarget Tacrine Hybrids with Neuroprotective Properties to Confront Alzheimer’s Disease
Spilovska K., Korabecny J., Nepovimova E., Dolezal R., Mezeiova E., Soukup O., Kuca K.
Current Topics in Medicinal Chemistry, 2016
16.
New Hybrids of 4-Amino-2,3-polymethylene-quinoline and p-Tolylsulfonamide as Dual Inhibitors of Acetyl- and Butyrylcholinesterase and Potential Multifunctional Agents for Alzheimer’s Disease Treatment
Makhaeva G.F., Kovaleva N.V., Boltneva N.P., Lushchekina S.V., Astakhova T.Y., Rudakova E.V., Proshin A.N., Serkov I.V., Radchenko E.V., Palyulin V.A., Bachurin S.O., Richardson R.J.
Molecules, 2020
17.
Huprines — an insight into the synthesis and biological properties
Mezeiova E., Soukup O., Korabecny J.
Russian Chemical Reviews, 2020
18.
Conjugates of tacrine and 1,2,4-thiadiazole derivatives as new potential multifunctional agents for Alzheimer’s disease treatment: Synthesis, quantum-chemical characterization, molecular docking, and biological evaluation
Makhaeva G.F., Kovaleva N.V., Boltneva N.P., Lushchekina S.V., Rudakova E.V., Stupina T.S., Terentiev A.A., Serkov I.V., Proshin A.N., Radchenko E.V., Palyulin V.A., Bachurin S.O., Richardson R.J.
Bioorganic Chemistry, 2020
19.
New Multifunctional Agents Based on Conjugates of 4-Amino-2,3-polymethylenequinoline and Butylated Hydroxytoluene for Alzheimer’s Disease Treatment
Makhaeva G.F., Kovaleva N.V., Rudakova E.V., Boltneva N.P., Lushchekina S.V., Faingold I.I., Poletaeva D.A., Soldatova Y.V., Kotelnikova R.A., Serkov I.V., Ustinov A.K., Proshin A.N., Radchenko E.V., Palyulin V.A., Richardson R.J., et. al.
Molecules, 2020
20.
Evaluation of antioxidant activity of vanillin by using multiple antioxidant assays
Tai A., Sawano T., Yazama F., Ito H.
Biochimica et Biophysica Acta - General Subjects, 2011
21.
Overview of the Role of Vanillin on Redox Status and Cancer Development
Bezerra D.P., Soares A.K., de Sousa D.P.
Oxidative Medicine and Cellular Longevity, 2016
22.
Novel vanillin derivatives: Synthesis, anti-oxidant, DNA and cellular protection properties
Scipioni M., Kay G., Megson I., Kong Thoo Lin P.
European Journal of Medicinal Chemistry, 2018
23.
Cholinesterase and carboxylesterase inhibitors as pharmacological agents
Makhaeva G.F., Rudakova E.V., Kovaleva N.V., Lushchekina S.V., Boltneva N.P., Proshin A.N., Shchegolkov E.V., Burgart Y.V., Saloutin V.I.
Russian Chemical Bulletin, 2019
24.
Novel tacrine-tryptophan hybrids: Multi-target directed ligands as potential treatment for Alzheimer's disease
Chalupova K., Korabecny J., Bartolini M., Monti B., Lamba D., Caliandro R., Pesaresi A., Brazzolotto X., Gastellier A., Nachon F., Pejchal J., Jarosova M., Hepnarova V., Jun D., Hrabinova M., et. al.
European Journal of Medicinal Chemistry, 2019
25.
The Role of Human Carboxylesterases in Drug Metabolism: Have We Overlooked Their Importance?
Casey Laizure S., Herring V., Hu Z., Witbrodt K., Parker R.B.
Pharmacotherapy, 2013
26.
10.1016/j.mencom.2021.09.005_b0130
Taylor
Biochemistry, 1989
27.
beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies.
Bartolini M., Bertucci C., Cavrini V., Andrisano V.
Biochemical Pharmacology, 2003
28.
Neuroprotective and Cholinergic Properties of Multifunctional Glutamic Acid Derivatives for the Treatment of Alzheimer’s Disease
Arce M.P., Rodríguez-Franco M.I., González-Muñoz G.C., Pérez C., López B., Villarroya M., López M.G., García A.G., Conde S.
Journal of Medicinal Chemistry, 2009
29.
10.1016/j.mencom.2021.09.005_b0145
Re
Biol. Med., 1999