Design, Synthesis, and Molecular Docking of Some Novel Tacrine Based Cyclopentapyranopyridine- and Tetrahydropyranoquinoline-Kojic Acid Derivatives as Anti-Acetylcholinesterase Agents.
Acetylcholinesterase
/ metabolism
Alzheimer Disease
/ drug therapy
Animals
Butyrylcholinesterase
/ metabolism
Cholinesterase Inhibitors
/ chemical synthesis
Drug Design
Electrophorus
Horses
Hydrogen Peroxide
/ antagonists & inhibitors
Molecular Docking Simulation
Molecular Structure
Neuroprotective Agents
/ chemical synthesis
PC12 Cells
Pyridines
/ chemical synthesis
Pyrones
/ chemical synthesis
Quinolines
/ chemical synthesis
Rats
Tacrine
/ analogs & derivatives
Alzheimer's disease
anti-acetylcholinesterase
cyclopentapyranopyridine-kojic acid
docking study
tetrahydropyranoquinoline-kojic acid
Journal
Chemistry & biodiversity
ISSN: 1612-1880
Titre abrégé: Chem Biodivers
Pays: Switzerland
ID NLM: 101197449
Informations de publication
Date de publication:
Jun 2021
Jun 2021
Historique:
received:
12
11
2020
accepted:
15
04
2021
pubmed:
17
4
2021
medline:
24
8
2021
entrez:
16
4
2021
Statut:
ppublish
Résumé
A novel series of tacrine based cyclopentapyranopyridine- and tetrahydropyranoquinoline-kojic acid derivatives were designed, synthesized, and evaluated as anti-cholinesterase agents. The chemical structures of all target compounds were characterized by
Identifiants
pubmed: 33861892
doi: 10.1002/cbdv.202000924
doi:
Substances chimiques
Cholinesterase Inhibitors
0
Neuroprotective Agents
0
Pyridines
0
Pyrones
0
Quinolines
0
Tacrine
4VX7YNB537
kojic acid
6K23F1TT52
Hydrogen Peroxide
BBX060AN9V
quinoline
E66400VT9R
Acetylcholinesterase
EC 3.1.1.7
Butyrylcholinesterase
EC 3.1.1.8
pyridine
NH9L3PP67S
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2000924Subventions
Organisme : Research Council of Hamadan University of Medical Sciences
ID : 9605103032
Informations de copyright
© 2021 Wiley-VHCA AG, Zurich, Switzerland.
Références
A. Kumar, A. Singh, E. Kavali, ‘A review on Alzheimer's disease pathophysiology and its management: an update’, Pharmacol. Rep. 2015, 67, 195-203.
J. Weller, A. Budson, ‘Current understanding of Alzheimer's disease diagnosis and treatment’, F1000Research. 2018, 7, F1000 Faculty Rev-1161.
A. Paula de Araujo Boleti, T. Michelle de Oliveira Flores, S. E. Moreno, L. D. Anjos, M. R. Mortari, L. Migliolo, ‘Neuroinflammation: an overview of neurodegenerative and metabolic diseases and of biotechnological studies’, Neurochem. Int. 2020, 104714.
A. Sharma, V. Pachauri, S. J. S. Flora, ‘Advances in Multi-Functional Ligands and the Need for Metal-Related Pharmacology for the Management of Alzheimer Disease’, Front. Pharmacol. 2018, 9, 1247.
C. Bellenguez, B. Grenier-Boley, J. C. Lambert, ‘Genetics of Alzheimer's disease: where we are, and where we are going’, Curr. Opin. Neurobiol. 2019, 61, 40-48.
E. Singh, G. Devasahayam, ‘Neurodegeneration by oxidative stress: a review on prospective use of small molecules for neuroprotection’, Mol. Biol. Rep. 2020, 47, 3133-3140.
A. M. Barron, S. J. Fuller, G. Verdile, R. N. Martins, ‘Reproductive hormones modulate oxidative stress in Alzheimer's disease’, Antioxid. Redox Signaling 2006, 8, 2047-2059.
A. V. Terry, J. J. Buccafusco, ‘The Cholinergic Hypothesis of Age and Alzheimer's Disease-Related Cognitive Deficits: Recent Challenges and Their Implications for Novel Drug Development’, J. Pharmacol. Exp. Ther. 2003, 306, 821-827.
D. S. Auld, T. J. Kornecook, S. Bastianetto, R. Quirion, ‘Alzheimer's disease and the basal forebrain cholinergic system: relations to beta-amyloid peptides, cognition, and treatment strategies’, Prog. Neurobiol. 2002, 68, 209-245.
L. Berg, C. D. Andersson, E. Artursson, A. Hörnberg, A.-K. Tunemalm, A. Linusson, F. Ekström, ‘Targeting acetylcholinesterase: identification of chemical leads by high throughput screening, structure determination and molecular modeling’, PLoS One 2011, 6, e26039-e26039.
X. Zhang, K. Rakesh, S. Bukhari, M. Balakrishna, H. Manukumar, H.-L. Qin, ‘Multi-targetable chalcone analogs to treat deadly Alzheimer's disease: current view and upcoming advice’, Bioorg. Med. Chem. 2018, 80, 86-93.
A. K. Sahoo, J. Dandapat, U. C. Dash, S. Kanhar, ‘Features and outcomes of drugs for combination therapy as multi-targets strategy to combat Alzheimer's disease’, J. Ethnopharmacol. 2018, 215, 42-73.
R. Hariri, Z. Afshar, M. Mahdavi, M. Safavi, M. Saeedi, Z. Najafi, R. Sabourian, E. Karimpour-Razkenari, N. Edraki, F. H. Moghadam, A. Shafiee, M. Khanavi, T. Akbarzadeh, ‘Novel Tacrine-Based Pyrano[3′,4′:5,6]pyrano[2,3-b]quinolinones: Synthesis and Cholinesterase Inhibitory Activity’, Arch. Pharm. 2016, 349, 915-924.
M. Bartolini, J. Marco-Contelles, ‘Tacrines as Therapeutic Agents for Alzheimer's Disease. IV. The Tacripyrines and Related Annulated Tacrines’, Chem. Rec. 2019, 19, 927-937.
M. Khoobi, F. Ghanoni, H. Nadri, A. Moradi, M. Pirali Hamedani, F. Homayouni Moghadam, S. Emami, M. Vosooghi, R. Zadmard, A. Foroumadi, A. Shafiee, ‘New tetracyclic tacrine analogs containing pyrano[2,3-c]pyrazole: Efficient synthesis, biological assessment and docking simulation study’, Eur. J. Med. Chem. 2015, 89, 296-303.
A. Balmori, M. Chioua, R. P. de la Bellacasa, R. Estrada-Tejedor, L. Ismaili, J. Marco-Contelles, J. I. Borrell, ‘5-Amino-6,7,8,9-Tetrahydrobenzo[b][1,8]Naphthyridin-2(1H)-One: The first Example of a new Family of HuperTacrines for Alzheimer's Disease Therapy’, ChemistrySelect 2017, 2, 2605-2610.
A. Romero, R. Cacabelos, M. J. Oset-Gasque, A. Samadi, J. Marco-Contelles, ‘Novel tacrine-related drugs as potential candidates for the treatment of Alzheimer's disease’, Bioorg. Med. Chem. Lett. 2013, 23, 1916-1922.
D. Silva, M. Chioua, A. Samadi, M. Carmo Carreiras, M.-L. Jimeno, E. Mendes, C. d. l. Ríos, A. Romero, M. Villarroya, M. G. López, J. Marco-Contelles, ‘Synthesis and pharmacological assessment of diversely substituted pyrazolo[3,4-b]quinoline, and benzo[b]pyrazolo[4,3-g][1,8]naphthyridine derivatives’, Eur. J. Med. Chem. 2011, 46, 4676-4681.
E. Maalej, F. Chabchoub, M. J. Oset-Gasque, M. Esquivias-Pérez, M. P. González, L. Monjas, C. Pérez, C. de los Ríos, M. I. Rodríguez-Franco, I. Iriepa, I. Moraleda, M. Chioua, A. Romero, J. Marco-Contelles, A. Samadi, ‘Synthesis, biological assessment, and molecular modeling of racemic 7-aryl-9,10,11,12-tetrahydro-7H-benzo[7,8]chromeno[2,3-b]quinolin-8-amines as potential drugs for the treatment of Alzheimer's disease’, Eur. J. Med. Chem. 2012, 54, 750-763.
A. E. A. Moneim, ‘Oxidant/Antioxidant imbalance and the risk of Alzheimer's disease’, Curr. Alzheimer Res. 2015, 12, 335-349.
W.-J. Huang, X. Zhang, W.-W. Chen, ‘Role of oxidative stress in Alzheimer's disease’, Biomed. Rep. 2016, 4, 519-522.
Y. Wu, Y.-g. Shi, L.-y. Zeng, Y. Pan, X.-y. Huang, L.-q. Bian, Y.-j. Zhu, R.-r. Zhang, J. Zhang, ‘Evaluation of antibacterial and anti-biofilm properties of kojic acid against five food-related bacteria and related subcellular mechanisms of bacterial inactivation’, Food Sci. Technol. Int. 2019, 25, 3-15.
G. Karakaya, A. Ercan, S. Oncul, M. D. Aytemir, ‘Synthesis and Cytotoxic Evaluation of Kojic Acid Derivatives with Inhibitory Activity on Melanogenesis in Human Melanoma Cells’, Anti-Cancer Agents Med. Chem. 2018, 18, 2137-2148.
M. L. Gonçalez, D. G. Marcussi, G. M. F. Calixto, M. A. Corrêa, M. Chorilli, ‘Structural Characterization and In Vitro Antioxidant Activity of Kojic Dipalmitate Loaded W/O/W Multiple Emulsions Intended for Skin Disorders’, BioMed Res. Int. 2015, 2015, 304591.
Z. Najafi, M. Mahdavi, M. Saeedi, E. Karimpour-Razkenari, N. Edraki, M. Sharifzadeh, M. Khanavi, T. Akbarzadeh, ‘Novel tacrine-coumarin hybrids linked to 1,2,3-triazole as anti-Alzheimer's compounds: In vitro and in vivo biological evaluation and docking study’, Bioorg. Med. Chem. 2019, 83, 303-316.
Z. Najafi, M. Mahdavi, M. Saeedi, E. Karimpour-Razkenari, R. Asatouri, F. Vafadarnejad, F. H. Moghadam, M. Khanavi, M. Sharifzadeh, T. Akbarzadeh, ‘Novel tacrine-1,2,3-triazole hybrids: In vitro, in vivo biological evaluation and docking study of cholinesterase inhibitors’, Eur. J. Med. Chem. 2017, 125, 1200-1212.
M. S. Asgari, H. Azizian, M. Nazari Montazer, M. Mohammadi-Khanaposhtani, M. Asadi, S. Sepehri, P. R. Ranjbar, R. Rahimi, M. Biglar, B. Larijani, M. Amanlou, M. Mahdavi, ‘New 1,2,3-triazole-(thio)barbituric acid hybrids as urease inhibitors: Design, synthesis, in vitro urease inhibition, docking study, and molecular dynamic simulation’, Arch. Pharm. 2020, 353, 2000023.
M. Chioua, E. Buzzi, I. Moraleda, I. Iriepa, M. Maj, A. Wnorowski, C. Giovannini, A. Tramarin, F. Portali, L. Ismaili, P. López-Alvarado, M. L. Bolognesi, K. Jóźwiak, J. C. Menéndez, J. Marco-Contelles, M. Bartolini, ‘Tacripyrimidines, the first tacrine-dihydropyrimidine hybrids, as multi-target-directed ligands for Alzheimer's disease’, Eur. J. Med. Chem. 2018, 155, 839-846.
R. M. Wadapurkar, M. D. Shilpa, A. K. S. Katti, M. B. Sulochana, ‘In silico drug design for Staphylococcus aureus and development of host-pathogen interaction network’, Inform. Med. Unlocked 2018, 10, 58-70.
S. Babaee, M. A. Zolfigol, M. Zarei, M. Abbasi, Z. Najafi, ‘Synthesis of pyridinium-based salts: Catalytic application at the synthesis of six membered O-heterocycles’, J. Mol. Catal. 2019, 475, 110403.
G. L. Ellman, K. D. Courtney, V. Andres, R. M. Featherstone, ‘A new and rapid colorimetric determination of acetylcholinesterase activity’, Biochem. Pharmacol. 1961, 7, 88-95.
G. M. Morris, D. S. Goodsell, R. S. Halliday, R. Huey, W. E. Hart, R. K. Belew, A. J. Olson, ‘Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function’, J. Comput. Chem. 1998, 19, 1639-1662.