Aminoalkyl-substituted flavonoids

synthesis, cholinesterase inhibition, β-amyloid aggregation, and neuroprotective study

Laleh Faraji, Hamid Nadri, Alireza Moradi, Bukhari Syed Nasir Abbas, Bahar Pakseresht, Farshad Homayouni Moghadam, Setareh Moghimi, Mohammad Abdollahi, Mehdi Khoobi, Alireza Foroumadi

Research output: Contribution to journalArticle

Abstract

In this manuscript, 17 aminoalkyl-substituted flavonoid derivatives were synthesized and their anticholinesterase, anti-beta-amyloid (Aβ) aggregation and neuroprotective activities were evaluated. The synthesized compounds were prepared through four-step reaction, started from the reaction between 2-hydroxyacetophenone and 4-methoxy benzaldehyde. Among the final compounds, 6j displayed the best anti-butyrylcholinesterase activity (IC50 = 0.335 μM). Moreover, compound 6i significantly protected PC12 neurons against H2O2-induced cell death. This compound could also inhibit acetylcholinesterase and self-induced Aβ peptide aggregation by 51.3% and 49.2%, respectively. The results indicated that compound 6i could be considered as a lead compound towards the discovery of disease-modifying drugs for Alzheimer’s disease (AD) therapy.

Original languageEnglish
Pages (from-to)974-983
Number of pages10
JournalMedicinal Chemistry Research
Volume28
Issue number7
DOIs
Publication statusPublished - 1 Jul 2019
Externally publishedYes

Fingerprint

Butyrylcholinesterase
Cholinesterase Inhibitors
Cholinesterases
Acetylcholinesterase
Flavonoids
Amyloid
Inhibitory Concentration 50
Alzheimer Disease
Cell Death
Agglomeration
Lead compounds
Neurons
Peptides
Cell death
Pharmaceutical Preparations
Derivatives
Therapeutics
2'-hydroxyacetophenone
Lead
4-anisaldehyde

Keywords

  • Alzheimer’s disease
  • Flavonoid
  • Synthetic chemistry

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

Cite this

Aminoalkyl-substituted flavonoids : synthesis, cholinesterase inhibition, β-amyloid aggregation, and neuroprotective study. / Faraji, Laleh; Nadri, Hamid; Moradi, Alireza; Syed Nasir Abbas, Bukhari; Pakseresht, Bahar; Moghadam, Farshad Homayouni; Moghimi, Setareh; Abdollahi, Mohammad; Khoobi, Mehdi; Foroumadi, Alireza.

In: Medicinal Chemistry Research, Vol. 28, No. 7, 01.07.2019, p. 974-983.

Research output: Contribution to journalArticle

Faraji, L, Nadri, H, Moradi, A, Syed Nasir Abbas, B, Pakseresht, B, Moghadam, FH, Moghimi, S, Abdollahi, M, Khoobi, M & Foroumadi, A 2019, 'Aminoalkyl-substituted flavonoids: synthesis, cholinesterase inhibition, β-amyloid aggregation, and neuroprotective study', Medicinal Chemistry Research, vol. 28, no. 7, pp. 974-983. https://doi.org/10.1007/s00044-019-02350-4
Faraji, Laleh ; Nadri, Hamid ; Moradi, Alireza ; Syed Nasir Abbas, Bukhari ; Pakseresht, Bahar ; Moghadam, Farshad Homayouni ; Moghimi, Setareh ; Abdollahi, Mohammad ; Khoobi, Mehdi ; Foroumadi, Alireza. / Aminoalkyl-substituted flavonoids : synthesis, cholinesterase inhibition, β-amyloid aggregation, and neuroprotective study. In: Medicinal Chemistry Research. 2019 ; Vol. 28, No. 7. pp. 974-983.
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