Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity

Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity Publisher Pubmed

Hariri R¹ ; Afshar Z¹ ; Mahdavi M² ; Safavi M³ ; Saeedi M^{4, 5} ; Najafi Z⁶ ; Sabourian R⁵ ; Karimpourrazkenari E⁵ ; Edraki N⁷ ; Moghadam FH⁸ ; Shafiee A¹ ; Khanavi M⁹ ; Akbarzadeh T^{1, 5}

Show Affiliations

1. Faculty of Pharmacy, Department of Medicinal Chemistry, Tehran University of Medical Sciences, Tehran, Iran
2. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
3. Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, Iran
4. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
5. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
6. Faculty of Pharmacy, Department of Medicinal Chemistry, Hamadan University of Medical Sciences, Hamadan, Iran
7. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
8. Department of Cellular Biotechnology at Cell Science Research Center, Royan Institute for Biotechnology, ACECR, Isfahan, Iran
9. Faculty of Pharmacy, Department of Pharmacognosy, Tehran University of Medical Sciences, Tehran, Iran

Source: Archiv der Pharmazie Published:2016

Abstract

In order to develop effective anti-cholinesterase compounds, a novel series of pyrano[3’,4’:5,6]pyrano[2,3-b]quinolinones were designed, synthesized, and evaluated in vitro against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). All derivatives showed very good AChE inhibitory (AChEI) activity (IC50 = 0.37–5.62 μM) compared with rivastigmine (IC50 = 11.07 μM). Among them, 11-amino-12-(2,3-dichlorophenyl)-3-methyl-7,8,9,10-tetrahydropyrano[3’,4’:5,6]pyrano[2,3-b]quinolin-1(12H)-one (6f) displayed the best inhibitory activity. However, most of the synthesized compounds showed no anti-BChE activity and compounds 6b and 6f were found to be only moderate inhibitors. The most potent anti-AChE compound 6f had low and moderate inhibitory activity and neuroprotective effects against beta-secretase (BACE1) and oxidative stress-induced cell death, respectively. Also, kinetic and molecular docking studies of binding interactions elucidated that compound 6f bound to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of AChE. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Style	Citing Format
MLA	Hariri R, et al.. "Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity." Archiv der Pharmazie, vol. 349, no. 12, 2016, pp. 915-924.
APA	Hariri R, Afshar Z, Mahdavi M, Safavi M, Saeedi M, Najafi Z, Sabourian R, Karimpourrazkenari E, Edraki N, Moghadam FH, Shafiee A, Khanavi M, Akbarzadeh T (2016). Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity. Archiv der Pharmazie, 349(12), 915-924.
Chicago	Hariri R, Afshar Z, Mahdavi M, Safavi M, Saeedi M, Najafi Z, Sabourian R, et al.. "Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity." Archiv der Pharmazie 349, no. 12 (2016): 915-924.
Harvard	Hariri R et al. (2016) 'Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity', Archiv der Pharmazie, 349(12), pp. 915-924.
Vancouver	Hariri R, Afshar Z, Mahdavi M, Safavi M, Saeedi M, Najafi Z, et al.. Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity. Archiv der Pharmazie. 2016;349(12):915-924.
BibTex	@article{ author = {Hariri R and Afshar Z and Mahdavi M and Safavi M and Saeedi M and Najafi Z and Sabourian R and Karimpourrazkenari E and Edraki N and Moghadam FH and Shafiee A and Khanavi M and Akbarzadeh T}, title = {Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity}, journal = {Archiv der Pharmazie}, volume = {349}, number = {12}, pages = {915-924}, year = {2016} }
RIS	TY - JOUR AU - Hariri R AU - Afshar Z AU - Mahdavi M AU - Safavi M AU - Saeedi M AU - Najafi Z AU - Sabourian R AU - Karimpourrazkenari E AU - Edraki N AU - Moghadam FH AU - Shafiee A AU - Khanavi M AU - Akbarzadeh T TI - Novel Tacrine-Based Pyrano[3’,4’:5,6]Pyrano[2,3-B]Quinolinones: Synthesis and Cholinesterase Inhibitory Activity JO - Archiv der Pharmazie VL - 349 IS - 12 SP - 915 EP - 924 PY - 2016 ER -

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