Synthesis and discovery of novel piperidone-grafted mono- and bis-spirooxindole-hexahydropyrrolizines as potent cholinesterase inhibitors

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 7, 2013, Pages 1696-1707

  Kia, Yalda ^a   Osman, Hasnah ^a   Kumar, Raju Suresh ^b   Murugaiyah, Vikneswaran ^c   Basiri, Alireza ^c   Perumal, Subbu ^d   Wahab, Habibah A ^c   Bing, Choi Sy ^c  

^a SCHOOL OF PHYSICS   (Malaysia)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c SCHOOL OF PHARMACEUTICAL SCIENCES   (Malaysia)

^d MADURAI KAMARAJ UNIVERSITY   (India)

Author keywords

1,3 Dipolar cycloaddition; AChE; BuChE; Selectivity and spiropyrrolizines

Indexed keywords

1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 2 CHLOROPHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 2 FLUOROPHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 2 METHOXY PHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 2 METHYLPHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 2,4 DICHLORO PHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 3 NITRO PHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 4 CHLOROPHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 4 FLUOROPHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) 4 METHYLPHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) NAPHTHYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; 1'' CARBONYL (SPIRO[2.3']OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 3'',5''BIS[(E) PHENYLMETHYLIDENE]TETRAHYDRO 4''(1H) PYRIDINONE; ACETYLCHOLINESTERASE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; ISATIN; OXINDOLE; PIPERIDONE DERIVATIVE; PYRROLIZINE DERIVATIVE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (2 CHLOROPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (2 CHLOROPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (2 FLUOROPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (2 FLUOROPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (2 METHOXYPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (2 METHOXYPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (2 METHYLPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (PHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (2,4 DICHLOROPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (2,4 DICHLOROPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (3 NITROPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (3 NITROPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (4 CHLOROPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (4 CHLOROPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (4 FLUOROPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (4 CHLOROPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (4 METHYLPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (4 METHYLPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (NAPHTHALEN 1 YLPHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (4 CHLOROPHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; SPIRO [2.3] OXINDOLE SPIRO[3.3''] 1'' CARBONYL(SPIRO[2.3]OXINDOLE HEXAHYDRO 1H PYRROLIZINE) 5'' (PHENYLMETHYLIDENE)TETRAHYDRO 4'' (1H) PYRIDINONE 4 (PHENYLMETHYLIDENE)HEXAHYDRO 1H PYRROLIZINE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; MOLECULAR DOCKING; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; SIMULATION;

ACETYLCHOLINESTERASE; BUTYRYLCHOLINESTERASE; CHOLINESTERASE INHIBITORS; HUMANS; INDOLES; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; PIPERIDONES; PYRROLES; SPIRO COMPOUNDS;

EID: 84875229746     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.01.066     Document Type: Article

References (36)

1. Alzheimer's Disease International World Alzheimer Report 2009 2009 Alzheimer's Disease International London
2. L.E. Hebert, P.A. Scherr, L.A. Beckett, M.S. Albert, D.M. Pilgrim, M.J. Chown, H.H. Funkenstein, and D.A. Evans JAMA 273 1995 1354
3. J.C. De la Torre Lancet Neurol. 3 2004 184
4. D.J. Selkoe J. Biol. Chem. 271 1996 18295
5. J. Hardy, and D.J. Selkoe Science 297 2002 353
6. A. Yanker Nat. Med. 2 1996 850
7. A. Nordberg Acta Neurol. Scand. 85 1992 54
8. A.V. Terry Jr., and J.J. Buccafusco J. Pharmacol. Exp. Ther. 306 2003 821
9. N. Tabet Age Ageing 35 2006 336
10. M. Mesulam, A. Guillozet, P. Shaw, and B. Quinn Neurobiol. Dis. 9 2002 88
11. E. Giacobini Neurochem. Int. 32 1998 413
12. A. Rampa, L. Piazzi, F. Belluti, S. Gobbi, A. Bisi, M. Bartolini, V. Andrisano, V. Cavrini, A. Cavalli, M. Recanatini, and P. Valenti J. Med. Chem. 44 2001 3810
13. D.J. Ramon, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602
14. A. Padwa 1,3-Dipolar Cycloaddition Chemistry Vol. 1 and 2 1984 Wiley New York, NY
15. G.A. Cordell Introduction to the Alkaloids: A Biogenetic Approach 1981 Wiley New York
16. B.P. Gangamani, V.A. Kumar, and K.N. Ganesh Tetrahedron 52 1996 15017
17. D.A. Klumpp, K.Y. Yeung, G.K.S. Prakash, and G.A. Olah J. Org. Chem. 63 1998 4481
18. S. Hilton, T. Ho, G. Pljevaljcic, and K. Jones Org. Lett. 2 2000 2639
19. S.N. Pandeya, and D. Sriram Acta Pharm. Turc. 40 1998 33
20. S.N. Pandeya, and D. Sriram Indian J. Pharm. Sci. 56 1999 174
21. R.S. Varma, and W.L. Nobles J. Med. Chem. 10 1967 972
22. S.N. Pandeya, P. Yogeeswari, D. Sriram, E. De Clercq, C. Pannecouque, and M. Witvrouw Chemotherapy 45 1999 192
23. S.A. Imam, and R.S. Varma Experientia 31 1975 1277
24. Y. Nicolet, O. Lockridge, P. Masson, J.C. Fontecilla-Camps, and F. Nachon J. Biol. Chem. 278 2003 41141
25. P.H. Axelsen, M. Harel, I. Silman, and J.L. Sussman Protein Sci. 3 1994 188
26. J.L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman Science 253 1991 872
27. M. Harel, D.M. Quinn, H.K. Nair, I. Silman, and J.L. Sussman JACS 118 1996 2340
28. M. Harel, I. Schalk, L. Ehret-Sabatier, F. Bouet, M. Goeldner, C. Hirth, P.H. Axelsen, I. Silman, and J.L. Sussman Proc. Natl. Acad. Sci. U.S.A. 90 1993 9031
29. L. Pezzementi, F. Nachon, and A. Chatonnet PLoS One 6 2011 1932
30. A.N. Çokuǧraş Turk. J. Biochem. 28 2003 54
31. J. Dimmock, M.P. Padmanilayam, R.N. Puthucode, A.J. Nazarali, N.L. Motaganahalli, G.A. Zello, J.W. Quail, E.O. Oloo, H.Z. Kraatz, and J.S. Prisciak J. Med. Chem. 44 2001 586
32. A. Basiri, V. Murugaiyah, H. Osman, M. Hemamalini, and H.K. Fun Acta Crystallogr., Sect. E 67 2011 o1301
33. Crystallographic data (excluding structure factors) for compounds 8a and 9k have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 906841 and 906842, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].
34. T. Ahmed, and A.H. Gilani Pharmacol. Biochem. Behav. 91 2009 554
35. A. Obregon, M. Schetinger, M.M. Correa, V.M. Morsch, J. Da Silva, M. Martins, H.G. Bonacorso, and N. Zanatta Neurochem. Res. 30 2005 379
36. H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov, and P.E. Bourne Nucleic Acids Res. 28 2000 235