Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study

Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study Publisher Pubmed

Ghafary S¹ ; Najafi Z^{2, 3} ; Mohammadikhanaposhtani M⁴ ; Nadri H⁵ ; Edraki N⁶ ; Ayashi N⁷ ; Larijani B⁷ ; Amini M^{1, 8} ; Mahdavi M⁷

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1. Faculty of Pharmacy, Department of Medicinal Chemistry, Tehran University of Medical Sciences, Tehran, Iran
2. Department of Medicinal Chemistry, School of Pharmacy, Hamadan University of Medical Sciences, Hamadan, Iran
3. Medicinal Plants and Natural Products Research Center, Hamadan University of Medical Sciences, Hamadan, Iran
4. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
5. Faculty of Pharmacy, Department of Medicinal Chemistry, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
6. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
7. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
8. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Archiv der Pharmazie Published:2018

Abstract

A novel series of cinnamic acid–tryptamine hybrids was designed, synthesized, and evaluated as cholinesterase inhibitors. Anticholinesterase assays showed that all of the synthesized compounds displayed a clearly selective inhibition of butyrylcholinesterase (BChE), but only a moderate inhibitory effect toward acetylcholinesterase (AChE) was detected. Among these cinnamic acid–tryptamine hybrids, compound 7d was found to be the most potent inhibitor of BChE with an IC50 value of 0.55 ± 0.04 μM. This compound showed a 14-fold higher inhibitory potency than the standard drug donepezil (IC50 = 7.79 ± 0.81 μM) and inhibited BChE through a mixed-type inhibition mode. Moreover, a docking study revealed that compound 7d binds to both the catalytic anionic site (CAS) and the peripheral anionic site (PAS) of BChE. Also, compound 7d was evaluated against β-secretase, which exhibited low activity (inhibition percentage: 38%). © 2018 Deutsche Pharmazeutische Gesellschaft

Style	Citing Format
MLA	Ghafary S, et al.. "Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study." Archiv der Pharmazie, vol. 351, no. 10, 2018, pp. -.
APA	Ghafary S, Najafi Z, Mohammadikhanaposhtani M, Nadri H, Edraki N, Ayashi N, Larijani B, Amini M, Mahdavi M (2018). Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study. Archiv der Pharmazie, 351(10), -.
Chicago	Ghafary S, Najafi Z, Mohammadikhanaposhtani M, Nadri H, Edraki N, Ayashi N, Larijani B, Amini M, Mahdavi M. "Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study." Archiv der Pharmazie 351, no. 10 (2018): -.
Harvard	Ghafary S et al. (2018) 'Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study', Archiv der Pharmazie, 351(10), pp. -.
Vancouver	Ghafary S, Najafi Z, Mohammadikhanaposhtani M, Nadri H, Edraki N, Ayashi N, et al.. Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study. Archiv der Pharmazie. 2018;351(10):-.
BibTex	@article{ author = {Ghafary S and Najafi Z and Mohammadikhanaposhtani M and Nadri H and Edraki N and Ayashi N and Larijani B and Amini M and Mahdavi M}, title = {Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study}, journal = {Archiv der Pharmazie}, volume = {351}, number = {10}, pages = {-}, year = {2018} }
RIS	TY - JOUR AU - Ghafary S AU - Najafi Z AU - Mohammadikhanaposhtani M AU - Nadri H AU - Edraki N AU - Ayashi N AU - Larijani B AU - Amini M AU - Mahdavi M TI - Novel Cinnamic Acid–Tryptamine Hybrids As Potent Butyrylcholinesterase Inhibitors: Synthesis, Biological Evaluation, and Docking Study JO - Archiv der Pharmazie VL - 351 IS - 10 SP - EP - PY - 2018 ER -

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