Synthesis and receptor binding studies of novel 4,4-disubstituted arylalkyl/arylalkylsulfonyl piperazine and piperidine-based derivatives as a new class of σ1 ligands

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 488-497

  Sadeghzadeh, Masoud ^a,b   Sheibani, Shahab ^a   Ghandi, Mehdi ^b   Daha, Fariba Johari ^a   Amanlou, Massoud ^c   Arjmand, Mohammad ^d   Hasani Bozcheloie, Abolfazl ^b  

^a NUCLEAR SCIENCE AND TECHNOLOGY RESEARCH INSTITUTE   (Iran)

^b UNIVERSITY OF TEHRAN   (Iran)

^c TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d PASTEUR INSTITUTE OF IRAN   (Iran)

Author keywords

1 Ligands; Halogenated sulfonamides; N arylalkylsulfonyl piperazine; N arylalkylsulfonyl piperidine; Sigma receptor ligand

Indexed keywords

1 (BENZYLSULFONYL) 4 (3 CHLOROBENZYL)PIPERAZINE; 1 (BENZYLSULFONYL) 4 (3 FLUOROBENZYL)PIPERAZINE; 1 (BENZYLSULFONYL) 4 (3 IODOBENZYL)PIPERAZINE; 1 (BENZYLSULFONYL) 4 (3 METHYLBENZYL)PIPERAZINE; 1 (BENZYLSULFONYL) 4 (4 BROMOBENZYL)PIPERAZINE; 1 (BENZYLSULFONYL) 4 (4 METHOXYBENZYL)PIPERAZINE; 1 BENZYL 4 (3 BROMOBENZYLSULFONYL)PIPERAZINE; 1 BENZYL 4 (3 CHLOROBENZYLSULFONYL)PIPERAZINE; 1 BENZYL 4 (3 IODOBENZYLSULFONYL)PIPERAZINE; 1 BENZYL 4 (3 METHYLBENZYLSULFONYL)PIPERAZINE; 1 BENZYL 4 (4 BROMOSTYRYLSULFONYL)PIPERAZINE; 1 BENZYL 4 (4 CHLOROPHENYLSULFONYL)PIPERAZINE; 1 BENZYL 4 (PHENETHYLSULFONYL)PIPERAZINE; 1 BENZYL 4 (PHENYLSULFONYL)PIPERAZINE; 4 BENZYL 1 (3 BROMOBENZYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (3 CHLOROBENZYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (3 IODOBENZYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (3 METHYLBENZYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (4 BROMOSTYRYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (4 CHLOROPHENYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (BENZYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (PHENETHYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (PHENYLSULFONYL)PIPERIDINE; 4 BENZYL 1 (STYRYLSULFONYL)PIPERIDINE; HALOPERIDOL; IBOGAINE; PENTAZOCINE; PIPERIDINE DERIVATIVE; SIGMA RECEPTOR LIGAND; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CRYSTALLIZATION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; RECEPTOR BINDING; ROOM TEMPERATURE; SUBSTITUTION REACTION;

ANIMALS; BINDING SITES; DOSE-RESPONSE RELATIONSHIP, DRUG; GUINEA PIGS; LIGANDS; MALE; MOLECULAR CONFORMATION; PIPERAZINES; PIPERIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, DOPAMINE D1; RECEPTORS, DOPAMINE D2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84877647740     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.04.013     Document Type: Article

References (51)

1. P.E. Gilbert, and W.R. Martin The effects of morphine- and nalorphine-like drugs in the nondependent, morphine-dependent and cyclazocine-dependent chronic spinal dog J. Pharmacol. Exp. Ther. 198 1976 66 82
2. R. Quirion, W.D. Bowen, Y. Itzhak, J.L. Junien, J.M. Musacchio, R.B. Rothman, T.P. Su, S.W. Tam, and D.P. Taylor A proposal for the classification of sigma binding sites Trends Pharmacol. Sci. 13 1992 85 86
3. J.M. Walker, W.D. Bowen, F.O. Walker, R.R. Matsumoto, B. De Costa, and K.C. Rice Sigma receptors: biology and function Pharmacol. Rev. 42 1990 355 402
4. T.-P. Su, and J.-L. Junien Sigma receptors in the central nervous system and the periphery Y. Itzhak, Sigma Receptors 1994 Academic Press London 21 44
5. S.A. Wolfe Jr., and E.B. De Souza Sigma and phencyclidine receptors in the brain-endocrine-immune axis NIDA Res. Monogr. 133 1993 95 123 (Pubitemid 23303291)
6. M. Hanner, F.F. Moebius, A. Flandorfer, H.G. Knaus, J. Striessnig, E. Kempner, and H. Glossmann Purification, molecular cloning, and expression of the mammalian sigma1-binding site Proc. Natl. Acad. Sci. U.S.A. 93 1996 8072 8077 (Pubitemid 26277167)
7. P. Seth, Y.-J. Fei, H.W. Li, W. Huang, F.H. Leibach, and V. Ganapathy Cloning and functional characterization of a σ receptor from rat brain J. Neurochem. 70 1998 922 931 (Pubitemid 28113624)
8. 1 receptor J. Neurochem. 70 1998 2279 2285
9. R. Kekuda, P.D. Prasad, Y.-J. Fei, F.H. Leibach, and V. Ganapathy Cloning and functional expression of the human type 1 sigma receptor (hSigmaR1) Biochem. Biophys. Res. Commun. 229 1996 553 558 (Pubitemid 27029069)
10. J. Xu, C. Zeng, W. Chu, F. Pan, J.M. Rothfuss, F. Zhang, Z. Tu, D. Zhou, D. Zeng, S. Vangveravong, F. Johnston, D. Spitzer, K.C. Chang, R.S. Hotchkiss, W.G. Hawkins, K.T. Wheeler, and R.H. Mach Identification of the PGRMC1 protein complex as the putative sigma-2 receptor binding site Nat. Commun. 2 2011 380
11. W.D. Bowen Sigma receptors: recent advances and new clinical potentials Pharm. Acta Helv. 74 2000 211 218 (Pubitemid 30182572)
12. B.J. Vilner, and W.D. Bowen Sigma receptors: recent advances and new clinical potentials J. Pharmacol. Exp. Ther. 292 2000 900 911
13. K. Matsuno, K. Matsunaga, T. Senda, and S. Mita Increase in extracellular acetylcholine level by sigma ligands in rat frontal cortex J. Pharmacol. Exp. Ther. 265 1993 851 859 (Pubitemid 23315597)
14. 3H]-dopamine release from rat striatal slices by sigma receptor ligands J. Pharmacol. Exp. Ther. 271 1994 212 219
15. G.A. Gudelsky Biphasic effect of sigma receptor ligands on the extracellular concentration of dopamine in the striatum of the rat J. Neural Transm. 106 1999 849 856 (Pubitemid 29516054)
16. 3H]-dopamine release from rat hippocampal slices through sigma-1 binding sites Neurochem. Int. 33 1998 29 34 (Pubitemid 28310713)
17. J.E. Bermack, and G. Debonnel Distinct modulatory roles of sigma receptor subtypes on glutamatergic responses in the dorsal hippocampus Synapse 55 2005 37 44 (Pubitemid 39565226)
18. 2+ signaling and cell survival Cell 131 2007 596 610 (Pubitemid 350017760)
19. S.-Y. Tsai, T. Hayashi, T. Mori, and T.-P. Su Sigma-1 receptor chaperones and diseases Cent. Nerv. Syst. Agents Med. Chem. 9 2009 184 189
20. N. Akhter, K. Shiba, K. Ogawa, S. Tsuji, S. Kinuya, K. Nakajima, and H. Mori A change of in vivo characteristics depending on specific activity of radioiodinated (+)-2-[4-(4-iodophenyl)piperidino]cyclohexanol [(+)-pIV] as a ligand for sigma receptor imaging Nucl. Med. Biol. 35 2008 29 34 (Pubitemid 350298249)
21. 2 receptor status of solid tumors with positron emission tomography J. Med. Chem. 50 2007 3194 3204 (Pubitemid 47065968)
22. B. Vilner, C.S. John, and W.D. Bowen Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines Cancer Res. 55 1995 408 413
23. R.H. Mach, C.R. Smith, and S.R. Childers Ibogaine possesses a selective affinity for sigma-2 receptors Life Sci. 57 1995 57 62
24. W.D. Bowen, C.M. Bertha, B.J. Vilner, and K.C. Rice CB-64D and CB-184: ligands with high sigma 2 receptor affinity and subtype selectivity Eur. J. Pharmacol. 278 1995 257 260
25. 1 receptor ligands Bioorg. Med. Chem. Lett. 14 2004 2217 2220
26. L. Costantino, F. Gandolfi, C. Sorbi, S. Franchini, O. Prezzavento, F. Vittori, G. Ronsisvalle, A. Leonardo, E. Poggesi, and L. Brasili Synthesis and structure-activity relationships of 1-aralkyl-4-benzylpiperidine and 1-aralkyl-4-benzylpiperazine derivatives as potent σ ligands J. Med. Chem. 48 2005 266 273 (Pubitemid 40105265)
27. S. Beduerftig, and B. Wuensch Chiral, nonracemic (piperazin-2-yl)methanol derivatives with σ-receptor affinity Bioorg. Med. Chem. 12 2004 3299 3311
28. 1 ligands Bioorg. Med. Chem. Lett. 15 2005 4833 4837 (Pubitemid 41354816)
29. S. Younes, Y. Labssita, G. Baziard-Mouysset, M. Payard, M.-C. Rettori, P. Renard, B. Pfeiffer, and D.-H. Caignard Synthesis and structure-activity relationships of novel arylalkyl 4-benzyl piperazine derivatives as σ site selective ligands Eur. J. Med. Chem. 35 2000 107 121 (Pubitemid 30136693)
30. S.Y. Ablordeppey, J.B. Fischer, H. Law, and R.A. Glennon Probing the proposed phenyl-A region of the sigma-1 receptor Bioorg. Med. Chem. 10 2002 2759 2765 (Pubitemid 34626239)
31. C. Mésangeau, E. Amata, W. Alsharif, M.J. Seminerio, M.J. Robson, R.R. Matsumoto, J.H. Poupaert, and C.R. McCurdy Synthesis and pharmacological evaluation of indole-based sigma receptor ligands Eur. J. Med. Chem. 46 2011 5154 5161
32. R.-J. Liu, J.A. Tucker, T. Zinevitch, O. Kirichenko, V. Konoplev, S. Kuznetsova, S. Sviridov, J. Pickens, S. Tandel, E. Brahmachary, and Y. Yang Design and synthesis of human immunodeficiency virus entry inhibitors: sulfonamide as an isostere for the alpha-ketoamide group J. Med. Chem. 50 2007 6535 6544 (Pubitemid 350309093)
33. W.G. Harter, H. Albrect, K. Brady, B. Caprathe, J. Dunbar, J. Gilmore, S. Hays, C.R. Kostlan, B. Lunney, and N. Walker The design and synthesis of sulfonamides as caspase-1 inhibitors Bioorg. Med. Chem. Lett. 14 2004 809 812 (Pubitemid 38120281)
34. N.S. Reddy, M.R. Mallireddigari, K.G. Cosenza, S.C. Bell, E.P. Reddy, and M.V.R. Reddy Synthesis of new coumarin 3-(N-aryl) sulfonamides and their anticancer activity Bioorg. Med. Chem. Lett. 14 2004 4093 4097 (Pubitemid 38844428)
35. B.R. Stranix, J.F. Lavallee, G. Sevigny, J. Yelle, V. Perron, N. Leberre, D. Herbart, and J.J. Wu Lysine sulfonamides as novel HIV-protease inhibitors: NÉ-acyl aromatic α-amino acids Bioorg. Med. Chem. Lett. 16 2006 3459 3462 (Pubitemid 43777110)
36. A. Shaabani, E. Soleimani, and A.H. Rezayan A novel approach for the synthesis of alkyl and aryl sulfonamides Tetrahedron. Lett. 48 2007 2185 2188 (Pubitemid 46275849)
37. C.S. John, B.B. Lim, B.J. Vilner, B.C. Geyer, and W.D. Bowen Substituted halogenated arylsulfonamides: a new class of sigma receptor binding tumor imaging agents J. Med. Chem. 41 1998 2445 2450 (Pubitemid 28321895)
38. H. Radeke, P.E. Persons, J.R. Hauske, Spirocyclic Ligands for Sigma Receptors, and Libraries and Methods of Use Thereof, US 2006/0194785 A1.
39. 1 receptor binding J. Med. Chem. 37 1994 1214 1219 (Pubitemid 24145383)
40. R.A. Glennon Pharmacophore identification for sigma-1 receptor binding Minirev. Med. Chem. 5 2005 927 940
41. M. Hamer, O.F. Batzer, M.J. Moats, C.C. Wu, and E.P. Lira Synthesis of 2-pyridyl-α-toluenesulfonates as antimalarials J. Pharm. Sci. 64 1975 1961 1964
42. P.A. Procopiou, V.J. Barrett, N.J. Bevan, K. Biggadike, P.R. Butchers, D.M. Coe, R. Conroy, D.D. Edney, R.N. Field, A.J. Ford, S.B. Guntrip, B.E. Looker, I.M. McLay, M.J. Monteith, V.S. Morrison, P.J. Mutch, S.A. Richards, R. Sasse, and C.E. Smith Synthesis and structure-activity relationships of long-acting beta2 adrenergic receptor agonists incorporating arylsulfonamide groups J. Med. Chem. 52 2009 2280 2288
43. R.A. Abramovitch, W.D. Holcomb, W.M. Thompson, and S. Wake Solution and flash vacuum pyrolyses of β-(3,5-disubstituted-phenyl)ethanesulfonyl azides, sultam, pyrindine, and azepine formation J. Org. Chem. 49 1984 5124 5131
44. M. Perez, M. Lamothe, C. Maraval, E. Mirabel, C. Loubat, B. Planty, C. Horn, J. Michaux, S. Marrot, R. Letienne, C. Pignier, A. Bocquet, F. Nadal-Wollbold, D. Cussac, L. De Vries, and B.L. Grand Discovery of novel protease activated receptors 1 antagonists with potent antithrombotic activity in vivo J. Med. Chem. 52 2009 5826 5836
45. B.M. Culbertson, and S. Dietz Some aromatic vinyl sulphonyl chlorides J. Chem. Soc. (C) 1968 992 993
46. M. McKinney, and R. Raddatz Curr. Protoc. Pharmacol. Suppl. 33 2006 1.3.1 1.3.42
47. 3H](+)-pentazocine to sigma recognition sites in guinea pig brain Eur. J. Pharmacol. 227 1992 371 378
48. S.Y. Ablordeppey, B. Fischer, and R.A. Glennon Is a nitrogen atom an important pharmacophoric element in sigma ligand binding? Bioorg. Med. Chem. 8 2000 2105 2111 (Pubitemid 30612502)
49. G. Baziard-Mouysset, S. Younes, Y. Labssita, M. Payard, D.-H. Caignard, M.-C. Rettori, P. Renard, B. Pfeiffer, and B. Guardiola-Lemaitre Synthesis and structure-activity relationships of novel 2-amino alkyl chromones and related derivatives as a site-selective ligands Eur. J. Med. Chem. 33 1998 339 347 (Pubitemid 28240087)
50. i) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction Biochem. Pharmacol. 22 1973 3099 3108
51. M.M. Bradford, A. Rapid, and Sensitive Method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 72 1976 248 254