Synthesis of highly functionalised dispiropyrrolidine derivatives as novel acetylcholinesterase inhibitors

Letters in Drug Design and Discovery

Volumn 11, Issue 2, 2014, Pages 156-161

  We, Ang Chee ^a   Ali, Mohamed Ashraf ^a,b,c   Yoon, Yeong Keng ^a   Ismail, Rusli ^e   Choon, Tan Soo ^a   Khaw, Kooi Yeong ^d   Murugaiyah, Vikneswaran ^d   Lakshmipathi, Venu Sanjeevi ^c  

^a INSTITUTE FOR RESEARCH IN MOLECULAR MEDICINE INFORMM   (Malaysia)

^b Alwar Pharmacy College   (India)

^c Sunrise University   (India)

^d SCHOOL OF PHYSICS   (Malaysia)

^e UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Acetyl cholinesterase inhibitors; Alzheimer's disease; Cycloaddition; Ellman's method; Lineweaver Burk plot; Molecular modeling; Pyrrolidine

Indexed keywords

CHOLINESTERASE; CHOLINESTERASE INHIBITOR; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION (PARAMETERS); DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ENZYME INHIBITION; IC 50; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84893778062     PISSN: 15701808     EISSN: 1875628X     Source Type: Journal    
DOI: 10.2174/15701808113109990038     Document Type: Article

References (21)

1. Ferri, C. P.; Prince, M.; Brayne, C.; Brodaty, H.; Fratiglioni, L.; Ganguli, M.; Hall, K.; Hasegawa, K.; Hendrie, H.; Huang, Y.; Jorm, A.; Mathers, C.; Menezes, P. R.; Rimmer, E.; Scazufca, M. Global prevalence of dementia: a Delphi consensus study. Lancet, 2005, 366(9503), 2112-2117
2. Szymanski, P.; Markowicz, M.; Mikiciuk-Olasik, E. Synthesis and biological activity of derivatives of tetrahydroacridine as acetylcholinesterase inhibitors. Bioorg. Chem., 2011, 39(4), 138-142
3. Scarpini, E.; Scheltens, P.; Feldman, H. Treatment of Alzheimer's disease: current status and new perspectives. Lancet. Neurol., 2003, 2(9), 539-547
4. Terry, A. V. Jr and Buccafusco, J. J. The Cholinergic Hypothesis of Age and Alzheimer's Disease-Related Cognitive Deficits: Recent Challenges and Their Implications for Novel Drug Development. J. Pharmacol. Exp. Ther., 2003, 306(3), 821- 827
5. Johnson, C. N.; Roland, A.; Upton, N. New symptomatic strategies in Alzheimer's disease. Drug Discovery Today Therap. Strategies., 2004, 1(1), 13-19
6. Szyma′nski, P.; Markowicz, M.; Bajda, M.; Malawska, B.; Mikiciuk-Olasi, E. Synthesis and biological activity of new 2,3- dihydro-1H-cyclopenta[b]-quinoline derivatives as acetylcholinesterase inhibitors Lett. Drug. Des. Discov., 2012, 9(7), 645-654
7. Zarotsky, V.; Sramek, J. J.; Cutler, N. R. Galantamine hydrobromide: An agent for Alzheimer's disease. Am. J. Health-Syst. Pharm., 2003, 60(5), 446-452
8. Macabeo, A. P. G.; Vidar, W. S.; Chen, X.; Decker, M.; Heilmann, J.; Wan, B.; Franzblau, S. G.; Galvez, E. V.; Aguinaldo, M. A. M.; Cordell, G. A. Mycobacterium tuberculosis and cholinesterase inhibitors from Voacanga globosa. Eur. J. Med. Chem., 2011, 46(7), 3118-3123
9. Cometa, M. F.; Fortuna, S.; Palazzino, G.; Volpe, M. T.; Salgado, E. R.; Nicoletti, M.; Tomassini, L. New cholinesterase inhibiting bisbenzylisoquinoline alkaloids from Abuta grandifolia. Fitoterapia, 2012, 83(3), 476-480
10. Kavitha, C. V.; Gaonkar, S. L.; Narendra Sharath Chandra, J. N.; Sadashiva, C. T.; Rangappa, K. S. Synthesis and screening for acetylcholinesterase inhibitor activity of some novel 2-butyl-1,3-diazaspiro[ 4,4]non-1-en-4-ones: Derivatives of irbesartan key intermediate. Bioorg. Med. Chem., 2007, 15(23), 7391-7398
11. Karthikeyan, S. V.; Devi Bala, B.; Paul Alex Raja, V.; Perumal, S.; Yogeeswari, P.; Sriram, D. A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiropyrrolothiazoles as antitubercular agents. Bioorg. Med. Chem. Lett., 2010, 20(1), 350-353
12. Sharma, P.; Kumar, A.; Sahu, V.; Upadhyay, S.; Singh, J. Synthesis of bioactive spiro- 2-[30-(20-phenyl)-3Hindolyl]-1-aryl-3- phenylaziridines and SAR studies on their antimicrobial behaviour. Med. Chem. Res., 2009, 18(5), 383-395
13. Wei, A. C.; Ali, M. A.; Yoon, Y. K.; Ismail, R.; Choon, T. S.; Kumar, R. S.; Arumugam, N.; Almansour, A. I.; Osman, H. Antimycobacterial activity: A facile three-component [3+2]- cycloaddition for the regioselective synthesis of highly functionalized dispiropyrrolidines. Bioorg. Med. Chem. Lett., 2012, 22(15), 4930-4933
14. Wei, A. C.; Ali, M. A.; Yoon, Y. K.; Ismail, R.; Choon, T. S.; Kumar, R. S. A facile three- component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines acting as antimycobacterial agents. Bioorg. Med. Chem. Lett.,2013, 23(5), 1383-1386
15. Ali, M. A.; Samy, J. G.; Manogaran, E.; Sellappan, V.; Hasan, M. Z.; Ahsan, M. J.; Pandian, S.; ShaharYar, M. Synthesis and antimycobacterial evaluation of novel 5,6- dimethoxy-1-oxo-2,5- dihydro-1H-2-indenyl-5,4- substituted phenyl methanone analogues. Bioorg. Med. Chem. Lett., 2009, 19(24), 7000-7002
16. Wei, A. C.; Ali, M. A.; Yoon, Y. K.; Quah, C. K.; Fun, H. K. 4′-(4- chlorophenyl)-1′- methyldispiro[indan-2,2′ pyrrolidine-3′, 2"- indan]-1,3,1"-trione. Acta Cryst., 2011, E67(9), o2404
17. Wei, A. C.; Ali, M. A.; Choon, T. S.; Abdul Razak, I.; Arshad, S. 7′-(2,5- dimethoxylphenyl)-5′,6′,7′,7a'- tetrahydrodispiro[indan-2,5′- pyrrolo[1,2-c]-[1,3]thiazole- 6́,2"-indan]-1,3,1"-trione. Acta. Cryst., 2012, E68(3), o560-561
18. 5S: C, 70.43; H, 4.93; N, 2.74. Found: C, 70.49; H, 5.01; N, 2.77.
19. Ellman, G. L.; Courtney, D.; Anddres, K. D. V.; Featherstone, R.M. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol., 1961, 7(2), 88-90
20. Silman, I.; Sussman, J. L. Acetylcholinesterase: How is structure related to function? Chem. Biol. Interact., 2008, 175(1-3), 3-10
21. Basiri, A.; Murugaiyah, V.; Osman, H.; Kumar, R. S.; Kia, Y.; Ali, M. A. Microwave assisted synthesis, cholinesterase enzymes inhibitory activities and molecular docking studies of new pyridopyrimidine derivatives. Bioorg. Med. Chem. Lett., 2013, 21(11), 3022-3031