4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study

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4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study Publisher

Hosseini F¹ ; Mohammadikhanaposhtani M² ; Azizian H³ ; Ramazani A¹ ; Tehrani MB⁴ ; Nadri H⁵ ; Larijani B⁶ ; Biglar M⁶ ; Adibi H⁶ ; Mahdavi M⁶

Show Affiliations

1. Department of Chemistry, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran
2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
3. Department of Medicinal Chemistry, School of Pharmacy-International Campus, Iran University of Medical Sciences, Tehran, Iran
4. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
5. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
6. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Structural Chemistry Published:2020

Abstract

A new series of 4-oxobenzo[d]1,2,3-triazin-pyridinium-phenylacetamide hybrids 8a–p was designed, synthesized, and screened as the potential cholinesterase inhibitors against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Obtained anti-cholinesterase activities demonstrated that all the title compounds exhibited excellent inhibition against BuChE and moderate inhibitory activity toward AChE in comparison to standard cholinesterase inhibitor donepezil. For example, compound 8e exhibited about 49-fold higher inhibitory activity than donepezil (IC50 = 3.2 ± 0.3 μM) against BuChE. This compound inhibited BuChE via a mixed-type inhibition mode. This finding demonstrated that compound 8e in addition to catalytic anionic site (CAS) can also interact with the peripheral anionic site (PAS) of BuChE. Molecular modeling and molecular dynamic studies were also performed on synthesized compounds. © 2020, Springer Science+Business Media, LLC, part of Springer Nature.

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Style	Citing Format
MLA	Hosseini F, et al.. "4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study." Structural Chemistry, vol. 31, no. 3, 2020, pp. 999-1012.
APA	Hosseini F, Mohammadikhanaposhtani M, Azizian H, Ramazani A, Tehrani MB, Nadri H, Larijani B, Biglar M, Adibi H, Mahdavi M (2020). 4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study. Structural Chemistry, 31(3), 999-1012.
Chicago	Hosseini F, Mohammadikhanaposhtani M, Azizian H, Ramazani A, Tehrani MB, Nadri H, Larijani B, Biglar M, Adibi H, Mahdavi M. "4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study." Structural Chemistry 31, no. 3 (2020): 999-1012.
Harvard	Hosseini F et al. (2020) '4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study', Structural Chemistry, 31(3), pp. 999-1012.
Vancouver	Hosseini F, Mohammadikhanaposhtani M, Azizian H, Ramazani A, Tehrani MB, Nadri H, et al.. 4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study. Structural Chemistry. 2020;31(3):999-1012.
BibTex	@article{ author = {Hosseini F and Mohammadikhanaposhtani M and Azizian H and Ramazani A and Tehrani MB and Nadri H and Larijani B and Biglar M and Adibi H and Mahdavi M}, title = {4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study}, journal = {Structural Chemistry}, volume = {31}, number = {3}, pages = {999-1012}, year = {2020} }
RIS	TY - JOUR AU - Hosseini F AU - Mohammadikhanaposhtani M AU - Azizian H AU - Ramazani A AU - Tehrani MB AU - Nadri H AU - Larijani B AU - Biglar M AU - Adibi H AU - Mahdavi M TI - 4-Oxobenzo[D]1,2,3-Triazin-Pyridinium-Phenylacetamide Derivatives As New Anti-Alzheimer Agents: Design, Synthesis, in Vitro Evaluation, Molecular Modeling, and Molecular Dynamic Study JO - Structural Chemistry VL - 31 IS - 3 SP - 999 EP - 1012 PY - 2020 ER -

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