title: A facile ionic liquid promoted synthesis, cholinesterase inhibitory activity and molecular modeling study of novel highly functionalized spiropyrrolidines.
abstract: A series of novel dimethoxyindanone embedded spiropyrrolidines were synthesized in ionic liquid, [bmim]Br and were evaluated for their inhibitory activities towards cholinesterases. Among the spiropyrrolidines, compound 4f exhibited the most potent activity with an IC50 value of 1.57 µM against acethylcholinesterase (AChE). Molecular docking simulation for the most active compound was employed with the aim of disclosing its binding mechanism to the active site of AChE receptor.
authors: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. almansor@ksu.edu.sa.
authors: Abdulrahman I
authors: AI
authors: Almansour
authors: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. sraju@ksu.edu.sa.
authors: Raju Suresh
authors: RS
authors: Kumar
authors: Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. aruorgchem@gmail.com.
authors: Natarajan
authors: N
authors: Arumugam
authors: School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden 11800, Malaysia. diba115920@gmail.com.
authors: Alireza
authors: A
authors: Basiri
authors: School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Malaysia. kia.yalda@yahoo.com.
authors: Yalda
authors: Y
authors: Kia
authors: Pharmacogenetic and Novel Therapeutic Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Malaysia. asraf80med@yahoo.com.
authors: Mohamed Ashraf
authors: MA
authors: Ali
authors: Institute of Pharmaceutical Science, King's College London, London SE1 9NH, UK. Mehvish.farooq@kcl.ac.uk.
authors: Mehvish
authors: M
authors: Farooq
authors: School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden 11800, Malaysia. vicky@usm.my.
authors: Vikneswaran
authors: V
authors: Murugaiyah
mesh_terms: D000110:Acetylcholinesterase / Q000737:chemistry; D020134:Catalytic Domain; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D052578:Ionic Liquids / Q000737:chemistry; D008958:Models, Molecular; D062105:Molecular Docking Simulation; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*
chemical_list: D002800:Cholinesterase Inhibitors; D052578:Ionic Liquids; D011759:Pyrrolidines; D013141:Spiro Compounds; D000110:Acetylcholinesterase
references: N Engl J Med. 2004 Jul 1;351(1):56-67
references: 15229308
references: Molecules. 2015 Jan 29;20(2):2296-309
references: 25642838
references: J Med Chem. 1976 Jul;19(7):892-8
references: 940109
references: Med Chem. 2014;10(5):512-20
references: 24138113
references: J Med Chem. 1972 Feb;15(2):129-32
references: 4332673
references: Bioorg Med Chem. 2014 Jan 15;22(2):906-16
references: 24369842
references: J Am Chem Soc. 2005 Mar 2;127(8):2398-9
references: 15724987
references: Curr Pharm Des. 2006;12(33):4377-87
references: 17105433
references: Chem Soc Rev. 2011 Mar;40(3):1383-403
references: 21116514
references: Bioorg Med Chem. 2013 Apr 1;21(7):1696-707
references: 23454132
references: Bioorg Med Chem Lett. 2009 Sep 1;19(17):5075-7
references: 19643609
references: Bioorg Med Chem. 2013 Jun 1;21(11):3022-31
references: 23602518
references: Bioorg Med Chem. 2014 Feb 15;22(4):1318-28
references: 24461561
references: Eur J Med Chem. 2013 Sep;67:221-9
references: 23871902
references: Chem Rev. 1999 Aug 11;99(8):2071-2084
references: 11849019
references: Org Lett. 2002 Jun 27;4(13):2197-9
references: 12074666
references: J Pharmacol Exp Ther. 2003 Sep;306(3):821-7
references: 12805474
references: Med Chem. 2014 Mar;10(2):228-36
references: 23627271
references: J Org Chem. 2004 Feb 20;69(4):1419-20
references: 14961709
references: Neuroscience. 2002;110(4):627-39
references: 11934471
references: Bioorg Med Chem Lett. 2013 May 15;23(10):2979-83
references: 23570788
references: Bioorg Med Chem Lett. 2014 Apr 1;24(7):1815-9
references: 24594354