Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH14370
RESEARCH ARTICLE
Contents Vol 68(6)

Ionic Liquid-Promoted Synthesis and Cholinesterase Inhibitory Activity of Highly Functionalized Spiropyrrolidines

Raju Suresh Kumar A E , Abdulrahman I. Almansour A , Natarajan Arumugam A , Alireza Basiri B , Yalda Kia C and Raju Ranjith Kumar D
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia.

B School of Pharmaceutical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia.

C School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia.

D Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, India.

E Corresponding author. Email: sraju@ksu.edu.sa

Australian Journal of Chemistry 68(6) 863-871 https://doi.org/10.1071/CH14370
Submitted: 9 June 2014  Accepted: 20 August 2014   Published: 21 October 2014

Abstract

A library of novel, highly functionalized spiropyrrolidines has been synthesized stereoselectively for the first time in ionic liquid medium employing [3+2] cycloaddition of a series of 2-arylmethylidene-5,6-dimethoxy-2,3-dihydro-1H-inden-1-ones with an unexplored azomethine ylide derived from acenaphthenequinone or isatin and tryptophan. These compounds were evaluated in vitro for their acetylcholinesterase and butyrylcholinesterase inhibitory activities. Molecular modelling simulation was performed to determine the binding interaction and orientation of these molecules in the active site gorge of the respective receptors.


References

[1]  R. V. A. Orru, M. de Greef, Synthesis 2003, 1471.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXmtVyqsbY%3D&md5=c9361e5a52d2b9f7144b1f99a0a517a2CAS |

[2]  D. J. Ramon, M. Yus, Angew. Chem. Int. Ed. 2005, 44, 1602.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXisFWkur8%3D&md5=121a8756ccaca4a530b2f80f83ea75d2CAS |

[3]  J. D. Sunderhaus, S. F. Martin, Chem. – Eur. J. 2009, 15, 1300.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsl2ht7Y%3D&md5=3708c68119c0737c7947ce8dc0c9aff9CAS | 19132705PubMed |

[4]  N. Isambert, R. Lavilla, Chem. – Eur. J. 2008, 14, 8444.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1OkurzI&md5=4534054c2df25829c317f1d8b8276a0dCAS | 18576454PubMed |

[5]  (a) C. Najera, J. M. Sansano, Angew. Chem. Int. Ed. 2005, 44, 6272.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFGmu7fF&md5=1752c83eef1b3304874ffe6ddcd04b36CAS |
      (b) I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765.
         | Crossref | GoogleScholarGoogle Scholar |
         (c) L. M. Harwood, R. J. Vickers, in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (Eds A. Padwa, W. H. Pearson) 2002, The Chemistry of Heterocyclic Compounds Vol. 59, pp. 169–252 (Wiley: New York, NY).
      (d) C. Najera, J. M. Sansano, Curr. Org. Chem. 2003, 7, 1105.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) G. Belanger, V. Darsigny, M. Dore, F. Levesque, Org. Lett. 2010, 12, 1396.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) E. Vedejs, G. R. Martinez, J. Am. Chem. Soc. 1979, 101, 6452.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) H. Pellissier, Tetrahedron 2007, 63, 3235.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) V. Nair, T. D. Suja, Tetrahedron 2007, 63, 12247.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) H. Jiang, J. Zhao, X. Han, S. Zhu, Tetrahedron 2006, 62, 11008.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtVyks7fP&md5=68033fb05ed307c409ae467cb6e140c0CAS |
      (b) E. Coutouli-Argyropoulou, P. Lianis, M. Mitakou, A. Giannoulis, J. Nowak, Tetrahedron 2006, 62, 1494.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) P. J. S. Gomes, C. M. Nunes, A. A. C. C. Pais, T. M. V. D. Pinho e Melo, L. G. Arnaut, Tetrahedron Lett. 2006, 47, 5475.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  M. A. Abou-Gharbia, P. H. Doukas, Heterocycles 1979, 12, 637.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXktl2hs78%3D&md5=e74cd43e62d178b963882630aed7a1cfCAS |

[8]  M. J. Kornet, A. P. Thio, J. Med. Chem. 1976, 19, 892.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE28XksVSltr8%3D&md5=5b03f2f5baa52ead83a29ad87e6ef634CAS | 940109PubMed |

[9]  K. Lundahl, J. Schut, J. L. M. A. Schlatmann, G. B. Paerels, A. Peters, J. Med. Chem. 1972, 15, 129.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38Xht1ahtbk%3D&md5=0c380f3cfce00a49d00a5c1d8d0f3624CAS | 4332673PubMed |

[10]  (a) T. Welton, Chem. Rev. 1999, 99, 2071.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXkt1artrw%3D&md5=af33471af673ca1d28a625ece5b21a98CAS | 11849019PubMed |
      (b) M. Petkovic, K. R. Seddon, L. P. N. Rebelo, C. S. Pereira, Chem. Soc. Rev. 2011, 40, 1383.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) Q. Yao, Org. Lett. 2002, 4, 2197.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. Kumar, S. S. Pawar, J. Org. Chem. 2004, 69, 1419.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) K. Fukumoto, M. Yoshizawa, H. Ohno, J. Am. Chem. Soc. 2005, 127, 2398.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  (a) S. A. Forsyth, U. Frohlich, P. Goodrich, H. Q. N. Gunaratne, C. Hardacre, A. McKeown, K. R. Seddon, New J. Chem. 2010, 34, 723.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXktVWrtL4%3D&md5=cf5274903626411fc6e6a7ac1a6acfadCAS |
      (b) J. Gao, Q.-W. Song, L.-N. He, C. Liu, Z.-Z. Yang, X. Han, X.-D. Li, Q.-C. Song, Tetrahedron 2012, 68, 3835.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G. G. K. S. N. Kumar, G. Aridoss, K. K. Laali, Tetrahedron Lett. 2012, 53, 3066.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  N. Isambert, M. M. S. Duque, J.-C. Plaquevent, Y. Genisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev. 2011, 40, 1347.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXit1KisLg%3D&md5=70ac4a1f096911ed4c53c67bca2b471dCAS | 20963207PubMed |

[13]  C. Mount, C. Downton, Nat. Med. 2006, 12, 780.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xms1eks7s%3D&md5=a4603d90703d0fb6ffbd71b4452240a4CAS | 16829947PubMed |

[14]  M. R. Farlow, M. L. Miller, V. Pejovic, Dement. Geriatr. Cogn. Disord. 2008, 25, 408.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltFOkt7k%3D&md5=6ff89a03cc9b88cfa5a5a1439962db04CAS | 18391487PubMed |

[15]  D. B. Kitchen, H. Decornez, J. R. Furr, J. Bajorath, Nat. Rev. Drug Discov. 2004, 3, 935.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXptFemtrg%3D&md5=1fb4c8d403b81926dd303436e26c9faaCAS | 15520816PubMed |

[16]  (a) R. S. Kumar, A. I. Almansour, N. Arumugam, H. Osman, M. A. Ali, A. Basiri, Y. Kia, Med. Chem. 2014, 10, 228.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisFOlu74%3D&md5=b1269b895458f010b02c80c1bba4f84aCAS | 23627271PubMed |
      (b) A. Basiri, V. Murugaiyah, H. Osman, R. S. Kumar, Y. Kia, A. Hooda, R. B. Parsons, Bioorg. Med. Chem. 2014, 22, 906.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) Y. Kia, H. Osman, R. S. Kumar, V. Murugaiyah, A. Basiri, S. Perumal, H. A. Wahab, C. S. Bing, Bioorg. Med. Chem. 2013, 21, 1696.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) A. Basiri, V. Murugaiyah, H. Osman, R. S. Kumar, Y. Kia, M. A. Ali, Bioorg. Med. Chem. 2013, 21, 3022.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) Y. Kia, H. Osman, R. S. Kumar, V. Murugaiyah, A. Basiri, S. Perumal, I. A. Razak, Bioorg. Med. Chem. Lett. 2013, 23, 2979.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) A. Basiri, V. Murugaiyah, H. Osman, R. S. Kumar, Y. Kia, K. B. Awang, M. A. Ali, Eur. J. Med. Chem. 2013, 67, 221.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) N. Arumugam, A. I. Almansour, R. S. Kumar, S. Perumal, H. A. Ghabbour, H.-K. Fun, Tetrahedron Lett. 2013, 54, 2515.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) R. S. Kumar, A. Ramar, S. Perumal, A. I. Almansour, N. Arumugam, M. A. Ali, Synth. Commun. 2013, 43, 2763.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) A. C. Wei, M. A. Ali, Y. K. Yoon, R. Ismail, T. S. Choon, R. S. Kumar, Bioorg. Med. Chem. Lett. 2013, 23, 1383.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) M. A. Ali, R. Ismail, T. S. Choon, R. S. Kumar, M. Asad, A. I. Almansour, Y. K. Yoon, A. C. Wei, K. Elumalai, S. Pandian, Med. Chem. 2012, 2, 7.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  M. A. Ali, M. S. Yar, M. Z. Hasan, M. J. Ahsan, S. Pandian, Bioorg. Med. Chem. Lett. 2009, 19, 5075.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVSlsrzP&md5=4923cf5b633bb670a7fd7dec882f1e9aCAS | 19643609PubMed |