New tetracyclic tacrine analogs containing pyrano[2,3-c]pyrazole: Efficient synthesis, biological assessment and docking simulation study

European Journal of Medicinal Chemistry

Volumn 89, Issue , 2015, Pages 296-303

  Khoobi, Mehdi ^a   Ghanoni, Farzaneh ^b   Nadri, Hamid ^c   Moradi, Alireza ^c   Hamedani, Morteza Pirali ^a   Moghadam, Farshad Homayouni ^c   Emami, Saeed ^d   Vosooghi, Mohsen ^a   Zadmard, Reza ^b   Foroumadi, Alireza ^a   Shafiee, Abbas ^a  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

^c SHAHID SADOUGHI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Acetylcholinesterase; Alzheimer's disease; Docking study; Neuroprotective activity; Tacrine

Indexed keywords

3 METHYL 4 (3 NITROPHENYL) 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 3 METHYL 4 (4 TOLYL) 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 3 METHYL 4 (NAPHTHALEN 1 YL) 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 3 METHYL 4 (THIOPHEN 1 YL) 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (2 FLUOROPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (2 METHOXYPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (2,3 DICHLOROPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (2,5 DIMETHOXYPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (3,4 DIMETHOXYPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (3,4,5 TRIMETHOXYPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (4 FLUOROPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; 4 (4 METHOXYPHENYL) 3 METHYL 2,4,6,7,8,9 HEXAHYDROPYRAZOLO[4',3':5,6]PYRANO[2,3 B]QUINOLIN 5 AMINE; ACETYLCHOLINESTERASE; BENZENE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; PYRANO[2,3 C] PYRAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; QUERCETIN; TACRINE; TACRINE DERIVATIVE; UNCLASSIFIED DRUG; FUSED HETEROCYCLIC RINGS; HYDROGEN PEROXIDE; NEUROPROTECTIVE AGENT; PYRAN DERIVATIVE;

ARTICLE; CELL VIABILITY; CHOLINESTERASE INHIBITION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; NEUROPROTECTION; OXIDATIVE STRESS; PC12 CELL LINE; ANALOGS AND DERIVATIVES; ANIMAL; BLOOD; CELL DEATH; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; ELECTROPHORUS; HORSE; KINETICS; MOLECULAR DOCKING; RAT; SYNTHESIS;

ANIMALS; BUTYRYLCHOLINESTERASE; CELL DEATH; CHOLINESTERASE INHIBITORS; DRUG DESIGN; ELECTROPHORUS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HORSES; HYDROGEN PEROXIDE; KINETICS; MOLECULAR DOCKING SIMULATION; NEUROPROTECTIVE AGENTS; PC12 CELLS; PYRANS; PYRAZOLES; RATS; TACRINE;

EID: 84908529735     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.10.049     Document Type: Article

References (33)

1. A.M. Palmer, Trends Pharmacol. Sci. 32 (2011) 141-147.
2. R. León, A.G. Garcia, J. Marco-Contelles, Med. Res. Rev. 33 (2013) 139-189.
3. P. Anand, B. Singh, Arch. Pharm. Res. 36 (2013) 375-399.
4. N.C. Inestrosa, A. Alvarez, C.A. Pérez, R.D. Moreno, M. Vicente, C. Linker, O.I. Casanueva, C. Soto, J. Garrido, Neuron 16 (1996) 881-891.
5. M. del Monte-Millán, E. García-Palomero, R. Valenzuela, P. Usán, C. de Austria, P. Muñoz-Ruiz, L. Rubio, I. Dorronsoro, A. Martínez, M. Medina, J. Mol. Neurosci. 30 (2006) 85-88.
6. A. Gella, N. Durany, Cell Adhes. Migr. 3 (2009) 88-93.
7. F.M. Longo, S.M. Massa, NeuroRx 1 (2004) 117-127.
8. B.J. Sahakian, A.M. Owen, N.J. Morant, S.A. Eagger, S. Boddington, L. Crayton, H.A. Crockford, M. Crooks, K. Hill, R. Levy, Psychopharmacology 110 (1993) 395-401.
9. P.B. Watkins, H.J. Zimmerman, M.J. Knapp, S.I. Gracon, K.W. Lewis, JAMA 271 (1994) 992-998.
10. D. Thomae, G. Kirsch, P. Seck, Synthesis (2007) 1027-1032.
11. D. Thomae, E. Perspicace, S. Hesse, G. Kirsch, P. Seck, Tetrahedron 64 (2008) 9309-9314.
12. H. Bekolo, G. Kirsch, Can. J. Chem. 85 (2007) 1-6.
13. D. Thomae, G. Kirsch, P. Seck, Synthesis (2008) 1600-1606.
14. C.-L. Yang, C.-H. Tseng, Y.-L. Chen, C.-M. Lu, C.-L. Kao, M.-H. Wu, C.-C. Tzeng, Eur. J. Med. Chem. 45 (2010) 602-607.
15. C. de Los Ríos, J. Egea, J. Marco-Contelles, R. León, A. Samadi, I. Iriepa, I. Moraleda, E. Gálvez, A.G. García, M.G. López, M. Villarroya, A. Romero, J. Med. Chem. 53 (2010) 5129-5143.
16. D. Silva, M. Chioua, A. Samadi, M. Carmo Carreiras, M.L. Jimeno, E. Mendes, L. Ríos Cde, A. Romero, M. Villarroya, M.G. López, J. Marco-Contelles, Eur. J. Med. Chem. 46 (2011) 4676-4681.
17. E. Maalej, F. Chabchoub, M.J. Oset-Gasque, M. Esquivias-Pérez, M.P. González, L. Monjas, C. Pérez, C. de los Ríos, M.I. Rodríguez-Franco, I. Iriepa, I. Moraleda, M. Chioua, A. Romero, J. Marco-Contelles, A. Samadi, Eur. J. Med. Chem. 54 (2012) 750-763.
18. E. Maalej, F. Chabchoub, A. Samadi, C. De los Rios, A. Perona, A. Morreale, J. Marco-Contelles, Bioorg. Med. Chem. Lett. 21 (2011) 2384-2388.
19. [a] H. Nadri, M. Pirali-Hamedani, M. Shekarchi, M. Abdollahi, V. Sheibani, M. Amanlou, A. Shafiee, A. Foroumadi, Bioorg. Med. Chem. 18 (2010) 6360-6366;
20. [b] M. Alipour, M. Khoobi, A. Foroumadi, H. Nadri, A. Moradi, A. Sakhteman, et al., Bioorg. Med. Chem. 20 (2012) 7214-7222;
21. M. Alipour, M. Khoobi, H. Nadri, A. Sakhteman, A. Moradi, M. Ghandi, et al., Arch. Pharm. Chem. Life Sci. 346 (2013) 577-587;
22. S.F. Razavi, M. Khoobi, H. Nadri, A. Sakhteman, et al., Eur. J. Med. Chem. 64 (2013) 252-259;
23. [e] M. Khoobi, M. Alipour, A. Moradi, A. Sakhteman, H. Nadri, et al., Eur. J. Med. Chem. 68 (2013) 291-300;
24. [f] M. Khoobi, M. Alipour, A. Sakhteman, H. Nadri, A. Moradi, et al., Eur. J. Med. Chem. 68 (2013) 260-269;
25. [g] H. Akrami, B.F. Mirjalili, M. Khoobi, H. Nadri, A. Moradi, et al., Eur. J. Med. Chem. 84 (2014) 375-381.
26. H. Mecadon, M.R. Rohman, I. Kharbangar, B.M. Laloo, I. Kharkongor, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52 (2011) 3228-3231.
27. M. Khoobi, M. Alipour, A. Moradi, A. Sakhteman, H. Nadri, S.F. Razavi, M. Ghandi, A. Foroumadi, A. Shafiee, Eur. J. Med. Chem. 68 (2013) 291-300.
28. G.L. Ellman, K.D. Courtney, V. Andres, R.M. Featherstone, Biochem. Pharmacol. 7 (1961) 88-95.
29. S.H. Koh, S.H. Kim, H. Kwon, Y. Park, K.S. Kim, C.W. Song, J. Kim, M.H. Kim, H.J. Yu, J.S. Henkel, H.K. Jung, Brain Res. Mol. Brain Res. 118 (2003) 72-81.
30. D. Zsolt, A. Juhász, M. Gálfi, K. Soós, R. Papp, D. Zádori, B. Penke, Brain Res. Bull. 62 (2003) 223-229.
31. O. Trott, A.J. Olson, J. Comput. Chem. 31 (2010) 455-461.
32. N.M. O'Boyle, M. Banck, C.A. James, C. Morley, T. Vandermeersch, G.R. Hutchison, J. Cheminform. 3 (2011) 33.
33. M.F. Sanner, A programming language for software integration and development, J. Mol. Graph. Model 17 (1999) 57-61.