SavedAdd your journal

Journals / Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi / 2022 / Cilt: 12 - Sayı: 3

Synthesis and Cholinesterase Inhibitory Potentials of (5-formylfuran-2-yl) methyl 3,4-dimethoxy/nitro benzoates

Mehmet KOCA
Pages
1345–1357
Publication Date
2022-10-18
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

These derivatives can be used to develop new drugs such as cholinesterase inhibitors.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Cholinesterase (ChE) inhibitors are an important group of drugs used in Alzheimer's, glaucoma, and myasthenia gravis.
📊
Key Findings & Data:In this study (5-formylfuran-2-yl) methyl 4-nitro benzoate (compound 1) and newly designed (5-formylfuran-2-yl) methyl 3,4-dimethoxybenzoate (compound 2) were synthesized.
💡
Conclusion & Impact:These derivatives can be used to develop new drugs such as cholinesterase inhibitors.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Benzoate · cholinesterase · inhibition

Abstract

Cholinesterase (ChE) inhibitors are an important group of drugs used in Alzheimer's, glaucoma, and myasthenia gravis. In recent years, cholinesterase inhibition potentials of compounds have been investigated in new drug discovery studies. In this study (5-formylfuran-2-yl) methyl 4-nitro benzoate (compound 1) and newly designed (5-formylfuran-2-yl) methyl 3,4-dimethoxybenzoate (compound 2) were synthesized. The chemical structures of the synthesized compounds were characterized by spectral data (HRMS, 1H NMR, and 13C NMR). The ChE inhibitory activity of the compounds was evaluated using in vitro colorimetric Ellman method. Compound 1 and compound 2 exhibited inhibitory activity against AChE at IC50 values of 3.25 μM and 8.45 μM, respectively. Compound 1 and Compound 2 showed inhibitory activity against BuChE at IC50 values of 8.45 μM and 14.44 μM, respectively. In Docking simulations with 1EVE and 1P0I, the binding free energy scores of compound 1 were higher than the binding free energy scores of compound 2. In this respect, in silico molecular docking studies overlapped with in vitro enzyme inhibition studies. These derivatives can be used to develop new drugs such as cholinesterase inhibitors.

🔖

Cite This Article

KOCA, M. (2022). Synthesis and Cholinesterase Inhibitory Potentials of (5-formylfuran-2-yl) methyl 3,4-dimethoxy/nitro benzoates. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, Cilt: 12 - Sayı: 3, 1345–1357. https://ajindex.com/articles/538396

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (8)

  1. Ali TB, Schleret TR, Reilly BM, Chen WY, Abagyan R, 2015, Adverse Effects of Cholinesterase Inhibitors in Dementia, According to the Pharmacovigilance Databases of the United-States and Canada. PloS one, 10(12): e0144337–e0144337. Bajda M, Wieckowska A, Hebda M, Szałaj N, Sotriffer C, Malawska B, 2013, Structure-Based Search for New Inhibitors of Cholinesterases. International journal of molecular sciences, 14: 5608–5632.
  2. Bourne Y, Taylor P, Radić Z, Marchot P, 2003, Structural Insights into Ligand Interactions at The Acetylcholinesterase Peripheral Anionic Site. The EMBO journal, 22(1): 1–12. Carotti A, de Candia M, Catto M, Borisova TN, Varlamov A V, Méndez-Álvarez E, Soto-Otero R, Voskressensky LG, Altomare C, 2006, Ester Derivatives of Annulated Tetrahydroazocines: A New Class of Selective Acetylcholinesterase Inhibitors. Bioorganic & Medicinal Chemistry, 14(21): 7205–7212.
  3. Chen Z-R, Huang J-B, Yang S-L, Hong F-F, 2022, Role of Cholinergic Signaling in Alzheimer’s Disease. Molecules, 27(6): 1816–1836.
  4. Colletier J-P, Fournier D, Greenblatt HM, Stojan J, Sussman JL, Zaccai G, Silman I, Weik M, 2006, Structural Insights into Substrate Traffic and Inhibition in Acetylcholinesterase. The EMBO Journal, 25(12): 2746–2756. Contestabile A, 2011, The History of The Cholinergic Hypothesis. Behavioural Brain Research, 221(2): 334–340.
  5. Dhorajiwala TM, Halder ST, Samant L, 2019, Comparative In Silico Molecular Docking Analysis of L-Threonine-3-Dehydrogenase, a Protein Target Against African Trypanosomiasis Using Selected Phytochemicals. Journal of Applied Biotechnology Reports, 6(3): 101–108.
  6. Ding Z, Luo X, Ma Y, Chen H, Qiu S, Sun G, Zhang W, Yu C, Wu Z, Zhang J, 2018, Eco-Friendly Synthesis of 5-Hydroxymethylfurfural (HMF) and Its Application to The Ferrier-Rearrangement Reaction. Journal of Carbohydrate Chemistry, 37: 1–13.
  7. Ellman GL, Courtney KD, Andres V, Featherstone RM, 1961, A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity. Biochemical Pharmacology, 7(2): 88–95. Giacobini E, 2003, Cholinergic Function and Alzheimer’s Disease. International Journal of Geriatric Psychiatry, 18(S1): S1–S5. Ha YZ, Mathew S, Yeong YK, 2020, Butyrylcholinesterase: A Multifaceted Pharmacological Target and Tool. Current Protein & Peptide Science, 21(1): 99–109.
  8. Johnson G, Moore WS, 2006, The Peripheral Anionic Site of Acetylcholinesterase: Structure, Functions and Potential Role in Rational Drug Design. Current Pharmaceutical Design, 12(2): 217–225. Karra