New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study

New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study Publisher Pubmed

Khoobi M¹ ; Ghanoni F² ; Nadri H³ ; Moradi A³ ; Hamedani MP¹ ; Moghadam FH⁴ ; Emami S⁵ ; Vosooghi M¹ ; Zadmard R² ; Foroumadi A¹ ; Shafiee A¹

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, 14176, Iran
2. Chemistry and Chemical Engineering Research Center of Iran (CCERCI), P.O. BOX 14335-186, Tehran, Iran
3. Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
4. Neurobiomedical Research Center, School of Medicine, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
5. Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran

Source: European Journal of Medicinal Chemistry Published:2015

Abstract

A new series of tacrine-based acetylcholinesterase (AChE) inhibitors 7a-l were designed by replacing the benzene ring of tacrine with aryl-dihydropyrano[2,3-c]pyrazole. The poly-functionalized hybrid molecules 7a-l were efficiently synthesized through multi-component reaction and subsequent Friedlander reaction between the obtained pyrano[2,3-c]pyrazoles and cyclohexanone. Most of target compounds showed potent and selective anti-AChE activity at sub-micromolar range. The most potent compound 7h bearing a 3,4-dimethoxyphenyl group was more active than reference drug tacrine. The representative compound 7h could significantly protect neurons against oxidative stress as potent as quercetin at low concentrations. The docking study of compound 7h with AChE enzyme revealed that the (R)-enantiomer binds preferably to CAS while the (S)-enantiomer prone to be a PAS binder. © 2014 Published by Elsevier Masson SAS.

Style	Citing Format
MLA	Khoobi M, et al.. "New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study." European Journal of Medicinal Chemistry, vol. 89, no. , 2015, pp. 296-303.
APA	Khoobi M, Ghanoni F, Nadri H, Moradi A, Hamedani MP, Moghadam FH, Emami S, Vosooghi M, Zadmard R, Foroumadi A, Shafiee A (2015). New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study. European Journal of Medicinal Chemistry, 89(), 296-303.
Chicago	Khoobi M, Ghanoni F, Nadri H, Moradi A, Hamedani MP, Moghadam FH, Emami S, et al.. "New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study." European Journal of Medicinal Chemistry 89, no. (2015): 296-303.
Harvard	Khoobi M et al. (2015) 'New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study', European Journal of Medicinal Chemistry, 89(), pp. 296-303.
Vancouver	Khoobi M, Ghanoni F, Nadri H, Moradi A, Hamedani MP, Moghadam FH, et al.. New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study. European Journal of Medicinal Chemistry. 2015;89():296-303.
BibTex	@article{ author = {Khoobi M and Ghanoni F and Nadri H and Moradi A and Hamedani MP and Moghadam FH and Emami S and Vosooghi M and Zadmard R and Foroumadi A and Shafiee A}, title = {New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study}, journal = {European Journal of Medicinal Chemistry}, volume = {89}, number = {}, pages = {296-303}, year = {2015} }
RIS	TY - JOUR AU - Khoobi M AU - Ghanoni F AU - Nadri H AU - Moradi A AU - Hamedani MP AU - Moghadam FH AU - Emami S AU - Vosooghi M AU - Zadmard R AU - Foroumadi A AU - Shafiee A TI - New Tetracyclic Tacrine Analogs Containing Pyrano[2,3-C]Pyrazole: Efficient Synthesis, Biological Assessment and Docking Simulation Study JO - European Journal of Medicinal Chemistry VL - 89 IS - SP - 296 EP - 303 PY - 2015 ER -

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