Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity

Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity Publisher

Faraji L¹ ; Shahkarami S² ; Nadri H³ ; Moradi A³ ; Saeedi M⁴ ; Foroumadi A¹ ; Ramazani A² ; Haririan I⁵ ; Ganjali MR⁶ ; Shafiee A¹ ; Khoobi M^{1, 5}

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy, Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
2. Department of Chemistry, University of Zanjan, PO Box 45195-313, Zanjan, Iran
3. Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
4. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
5. Department of Pharmaceutical Biomaterials, Medical Biomaterials Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
6. Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, Tehran, Iran

Source: Journal of Chemical Research Published:2017

Abstract

A series of 20 novel benzimidazole and benzothiazole derivatives linked to a 1,2,3-triazole ring system was synthesised, characterised and evaluated for in vitro acetylcholinesterase (AChE) inhibitory activity. Several copper catalysts and solvents were screened to establish the optimal conditions for the preparation of the target compounds. Three different linkers were used to optimise the enzyme inhibitory effect. Out of the 20 compounds, 13 showed some AChE inhibition. The most potent compound, which showed 84% inhibition at 100 μM, contained a 1-(2-fluorobenzyl)-1,2,3-triazole linked to a benzimidazole group. A docking simulation study showed that the most active compound bound preferentially to the catalytic anionic subsite of the AChE enzyme. © 2017, Science Reviews 2000 Ltd. All rights reserved.

Style	Citing Format
MLA	Faraji L, et al.. "Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity." Journal of Chemical Research, vol. 41, no. 1, 2017, pp. 30-35.
APA	Faraji L, Shahkarami S, Nadri H, Moradi A, Saeedi M, Foroumadi A, Ramazani A, Haririan I, Ganjali MR, Shafiee A, Khoobi M (2017). Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity. Journal of Chemical Research, 41(1), 30-35.
Chicago	Faraji L, Shahkarami S, Nadri H, Moradi A, Saeedi M, Foroumadi A, Ramazani A, et al.. "Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity." Journal of Chemical Research 41, no. 1 (2017): 30-35.
Harvard	Faraji L et al. (2017) 'Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity', Journal of Chemical Research, 41(1), pp. 30-35.
Vancouver	Faraji L, Shahkarami S, Nadri H, Moradi A, Saeedi M, Foroumadi A, et al.. Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity. Journal of Chemical Research. 2017;41(1):30-35.
BibTex	@article{ author = {Faraji L and Shahkarami S and Nadri H and Moradi A and Saeedi M and Foroumadi A and Ramazani A and Haririan I and Ganjali MR and Shafiee A and Khoobi M}, title = {Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity}, journal = {Journal of Chemical Research}, volume = {41}, number = {1}, pages = {30-35}, year = {2017} }
RIS	TY - JOUR AU - Faraji L AU - Shahkarami S AU - Nadri H AU - Moradi A AU - Saeedi M AU - Foroumadi A AU - Ramazani A AU - Haririan I AU - Ganjali MR AU - Shafiee A AU - Khoobi M TI - Synthesis of Novel Benzimidazole and Benzothiazole Derivatives Bearing a 1,2,3-Triazole Ring System and Their Acetylcholinesterase Inhibitory Activity JO - Journal of Chemical Research VL - 41 IS - 1 SP - 30 EP - 35 PY - 2017 ER -

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