Design, synthesis and pharmacological evaluation of N-[4-(4-(alkyl/aryl/heteroaryl)-piperazin-1-yl)-phenyl]-carbamic acid ethyl ester derivatives as novel anticonvulsant agents

Bioorganic and Medicinal Chemistry Letters

Volumn 25, Issue 5, 2015, Pages 1092-1099

  Kumari, Shikha ^a   Mishra, Chandra Bhushan ^a   Tiwari, Manisha ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

Anticonvulsant; Epilepsy; Kindling; Oxidative stress; Piperazine

Indexed keywords

3,4 METHYLENEDIOXYAMPHETAMINE; ANTICONVULSIVE AGENT; DICHLOROMETHANE; DIMETHYL SULFOXIDE; ESTER DERIVATIVE; GLUTATHIONE; GLUTATHIONE PEROXIDASE; MALONALDEHYDE; N [4 [4 (ALKYL ARYL HETEROARYL) PIPERAZIN 1 YL] PHENYL] CARBAMIC ACID ETHYL ESTER DERIVATIVE; N,N DIMETHYLFORMAMIDE; NITRIC OXIDE; PENTETRAZOLE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG; CARBAMIC ACID; CARBAMIC ACID DERIVATIVE; PIPERAZINE;

ANTICONVULSANT ACTIVITY; ARTICLE; BLOOD BRAIN BARRIER; COLUMN CHROMATOGRAPHY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG CONJUGATION; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ELECTROSHOCK SEIZURE; EPILEPTOGENESIS; HUMAN; IN VIVO STUDY; INFRARED SPECTROSCOPY; INTESTINE ABSORPTION; LIPID PEROXIDATION; MASS SPECTROMETRY; NEUROTOXICITY; NONHUMAN; OXIDATIVE STRESS; PENTYLENETETRAZOLE-INDUCED SEIZURE; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; ROTAROD TEST; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMICALLY INDUCED; CHEMISTRY; ELECTRIC SHOCK; EPILEPSY; MOUSE; SEIZURES; SYNTHESIS;

ANIMALIA;

ANIMALS; ANTICONVULSANTS; CARBAMATES; DRUG DESIGN; ELECTROSHOCK; EPILEPSY; MICE; PENTYLENETETRAZOLE; PIPERAZINES; SEIZURES;

EID: 84922754472     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2015.01.004     Document Type: Article

References (43)

1. Y. Bozzi, M. Dunleavy, and D.C. Henshall FNBEH 5 2011 1
2. WHO data available from http://www.who.int/mediacentre/factsheets/fs999/en/.
3. H.S. White Epilepsia 44 2003 2
4. W. Loscher Trends Pharmacol. Sci. 23 2002 113
5. M.J. Brodie, and P. Kwan Epilepsia 53 2012 40
6. A. Pietrzycka, M. Stepniewski, A.M. Waszkielewicz, and H. Marona Acta Pol. Pharm. 63 2006 19
7. B. Chaetan, M. Bunha, M. Jagrat, N.B. Sinha, P. Saiko, G. Graser, T. Szekeres, G. Raman, P. Rajendran, D. Moorthy, A. Basu, and V. Jayaprakash Bioorg. Med. Chem. Lett. 20 2010 3906
8. Y. Chen, S. Wang, X. Xu, X. Liu, M. Yu, S. Zhao, S. Liu, Y. Qiu, T. Zhang, B.F. Liu, and G. Zhang J. Med. Chem. 56 2013 4671
9. D. Nozawa, T. Okubo, T. Ishii, S. Chaki, S. Okuyama, and A. Nakazato Bioorg. Med. Chem. 15 2007 2375
10. M. Khatri, K.S. Rai, S. Alam, A. Vij, and M. Tiwari Bioorg. Med. Chem. 17 2009 1890
11. J. Sapa, B. Filipek, K. Kulig, and B. Malawska Pharmacol. Rep. 63 2011 71
12. M.A. Siddiqui, and S.J. Keam Drugs 66 2006 693
13. C.S. Kumar, K. Vinaya, J.N. Chandra, N.R. Thimmegowda, S.B. Prasad, C.T. Sadashiva, and K.S. Rangappa J. Enzyme Inhib. Med. Chem. 4 2008 462
14. O. Kondoh, Y. Inagaki, H. Fukuda, E. Mizuguchi, Y. Ohya, M. Arisawa, N. Shimma, Y. Aoki, M. Sakaitani, and T. Watanabe Biol. Pharm. Bull. 11 2005 2138
15. P.Y.H. Choo, J.B. Chung, and H.S. Chung Bioorg. Med. Chem. Lett. 9 1999 2727
16. J.R. Tagat, R.W. Steensma, S.W. McCombie, D.V. Nazareno, S.I. Lin, B.R. Neustadt, K. Cox, S. Xu, L. Wojcik, M.G. Murray, N. Vantuno, B.M. Baroudy, and J.M. Strizki J. Med. Chem. 44 2001 3343
17. A.G. Chapman, G.P. Hart, B.S. Meldrum, L. Turski, and J.C. Watkins Neurosci. Lett. 55 1985 325
18. G.D. Novack, L.G. Stark, and S.L. Peterson J. Pharm. Exp. Ther. 208 1979 480
19. S. Patel, A.G. Chapman, J.L. Graham, B.S. Meldrum, and P. Frey Epilepsy Res. 7 1990 3
20. I.J. Boksay, K. Popendiker, R.O. Weber, and A. Soder Arzneimittelforschung 29 1979 193
21. D. Dauzonnel, J.M. Gillardin, F. Lepage, R. Pointetl, S. Risk, G. Lamottel, and P. Demersemanl Eur. J. Med. Chem. 30 1995 53
22. L.K. Desmedt, C.J. Niemegeers, and P.A. Janssen Arzneimittelforschung 25 1975 1408
23. K. Unverferth, J. Engel, N. Hofgen, A. Rostock, R. Gunther, H.J. Lankau, M. Menzer, A. Rolfs, J. Liebscher, B. Muller, and H.J. Hofmann J. Med. Chem. 41 1999 63
24. P. Meena, A. Manral, V. Saini, and M. Tiwari Neurotox. Res. 2014 10.1007/s12640-014-9499-3
25. Cheminformatics accessed on web: http://www.molinspiration.com/cgi-bin/properties.
26. D.F. Veber, S.R. Johnson, H.Y. Cheng, B.R. Smith, K.W. Ward, and K.D. Kopple J. Med. Chem. 45 2002 2615
27. A.K. Ghose, T. Herbertz, R.L. Hudkins, B.D. Dorsey, and J.P. Mallamo ACS Chem. Neurosci. 3 2012 50
28. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Adv Drug Delivery Rev. 46 2001 3
29. P. Ponnan, S. Gupta, M. Chopra, R. Tandon, A.S. Baghel, G. Gupta, A.K. Prasad, R.C. Rastogi, M. Bose, and H.G. Raj ISRN Struct. Biol. 2013 1
30. M.A. Rogawski Epilepsy Res. 68 2006 22
31. W. Loscher Handbook of Experimental Pharmacology Vol. 138 1999 Springer Berlin Heidelberg Publisher 19
32. J.R. Dimmock, R.N. Puthucode, J.M. Smith, M. Hetherington, J.W. Quail, U. Pugazhenthi, T. Lechler, and J.P. Stables J. Med. Chem. 36 1996 3984
33. R.J. Porter, J.J. Cereghino, G.D. Gladding, B.J. Hessie, H.J. Kupferberg, B. Scoville, and B. White Cleve. Clin. Q. 51 1984 293
34. P.T. Flaherty, T.D. Greenwood, A.L. Manheim, and J.F. Wolfe J. Med. Chem. 39 1996 1509
35. B.J. Jones, and D.J. Roberts J. Pharm. Pharmacol. 20 1968 302
36. N.Y. Lukomskaya, V.V. Lavrenteva, L.A. Starshinova, E.P. Zabkho, L.V. Gorbunova, T.B. Tikhonova, V.E. Gmiro, and L.G. Magazanik Neurosci. Behav. Physiol. 37 2007 75
37. M. Bialer Epilepsia 53 2012 3
38. T. Ito, T. Suzuki, and S.E. Wellman Life Sci. 59 1996 169
39. E.J. Shin, J.H. Jeong, Y.H. Chung, W.K. Kim, K. HoKo, J.H. Bach, J.S. Hong, Y. Yoneda, and H.C. Kim Neurochem. Int. 59 2011 122
40. M. Patel Free Radical Biol. Med. 2004 1951 37
41. A.N.V.D. Pol, K. Obrietan, and A. Belousov Neuroscience 74 1996 653
42. R. Kovacs, A. Rabanus, J. Otahal, A. Patzak, J. Kardos, K. Albus, U. Heinemann, and O. Kann J. Neurosci. 26 2009 8565
43. K. Itoh, and M. Watanabe Neuroscience 159 2009 735