Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors

Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors Publisher Pubmed

Arab S¹ ; Sadatebrahimi SE¹ ; Mohammadikhanaposhtani M¹ ; Moradi A² ; Nadri H² ; Mahdavi M¹ ; Moghimi S¹ ; Asadi M¹ ; Firoozpour L³ ; Piralihamedani M¹ ; Shafiee A¹ ; Foroumadi A¹

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy, Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
2. Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
3. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Archiv der Pharmazie Published:2015

Abstract

A novel series of chroman-4-one derivatives containing the N-benzyl pyridinium moiety were designed, synthesized, and evaluated for their acetylcholinesterase (AChE) inhibitory activities. Among the various synthesized compounds, (E)-1-(2,3-dibromobenzyl)-4-((7-ethoxy-4-oxochroman-3-ylidene)methyl)pyridinium bromide (8l) depicted the most potent anti-AChE activity (IC50=0.048μM). In addition, the molecular modeling study allowed us to detect possible binding modes that are in full compliance with the observed results through in vitro experiments. A novel series of chroman-4-one derivatives bearing N-benzyl pyridinium derivatives (8a-l) were synthesized and evaluated in vitro for their acetylcholinesterase inhibitory activities. The most promising compound, (E)-1-(2,3-dibromobenzyl)-4-((7-ethoxy-4-oxochroman-3-ylidene)methyl)pyridinium bromide 8l, showed an IC50 value of 0.048μM. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Style	Citing Format
MLA	Arab S, et al.. "Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors." Archiv der Pharmazie, vol. 348, no. 9, 2015, pp. 643-649.
APA	Arab S, Sadatebrahimi SE, Mohammadikhanaposhtani M, Moradi A, Nadri H, Mahdavi M, Moghimi S, Asadi M, Firoozpour L, Piralihamedani M, Shafiee A, Foroumadi A (2015). Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors. Archiv der Pharmazie, 348(9), 643-649.
Chicago	Arab S, Sadatebrahimi SE, Mohammadikhanaposhtani M, Moradi A, Nadri H, Mahdavi M, Moghimi S, et al.. "Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors." Archiv der Pharmazie 348, no. 9 (2015): 643-649.
Harvard	Arab S et al. (2015) 'Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors', Archiv der Pharmazie, 348(9), pp. 643-649.
Vancouver	Arab S, Sadatebrahimi SE, Mohammadikhanaposhtani M, Moradi A, Nadri H, Mahdavi M, et al.. Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors. Archiv der Pharmazie. 2015;348(9):643-649.
BibTex	@article{ author = {Arab S and Sadatebrahimi SE and Mohammadikhanaposhtani M and Moradi A and Nadri H and Mahdavi M and Moghimi S and Asadi M and Firoozpour L and Piralihamedani M and Shafiee A and Foroumadi A}, title = {Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors}, journal = {Archiv der Pharmazie}, volume = {348}, number = {9}, pages = {643-649}, year = {2015} }
RIS	TY - JOUR AU - Arab S AU - Sadatebrahimi SE AU - Mohammadikhanaposhtani M AU - Moradi A AU - Nadri H AU - Mahdavi M AU - Moghimi S AU - Asadi M AU - Firoozpour L AU - Piralihamedani M AU - Shafiee A AU - Foroumadi A TI - Synthesis and Evaluation of Chroman-4-One Linked to N-Benzyl Pyridinium Derivatives As New Acetylcholinesterase Inhibitors JO - Archiv der Pharmazie VL - 348 IS - 9 SP - 643 EP - 649 PY - 2015 ER -

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