Non-imidazole histamine H3 receptor ligands incorporating antiepileptic moieties

European Journal of Medicinal Chemistry

Volumn 77, Issue , 2014, Pages 269-279

  Sadek, Bassem ^a   Schwed, Johannes Stephan ^b,c   Subramanian, Dhanasekaran ^a   Weizel, Lilia ^b   Walter, Miriam ^b   Adem, Abdu ^a   Stark, Holger ^b,c  

^a UNITED ARAB EMIRATES UNIVERSITY   (United Arab Emirates)

^b GOETHE UNIVERSITY   (Germany)

^c HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Anticonvulsant activity; Convulsion; Epilepsy; GPCR; Histamine; Pharmacophore elements; Phenytoin

Indexed keywords

1 [3 [4 (3,5 DIMETHYL 4H 1,2,4 TRIAZOL 4 YL)PHENOXY]PROPYL]PIPERIDINE; 2 [4 [3 (PIPERIDIN 1 YL)PROPYOXY]BENZYLAMINO]PROPANE AMIDE DIHYDROGENOXALATE; 3 [5 METHYL 4 [4 [3 (PIPERIDIN 1 YL)PROPOXY]PHENYL] 4H 1,2,4 TRIAZOL 3 YL]PYRIDINE DIHYDROGENOXALATE; 5,5 DIPHENYL 3 [3 (PIPERIDIN 1 YL)PROPYL]IMIDAZOLIDINE 2,4 DIONE; 5,5 DIPHENYL 3 [4 [3 (PIPERIDIN 1 YL)PROPOXY]BENZYL]IMIDAZOLIDINE 2,4 DIONE; ACETOHYDRAZIDE; ANTICONVULSIVE AGENT; HISTAMINE H3 RECEPTOR; HISTAMINE H3 RECEPTOR AGONIST; PHENYTOIN; PITOLISANT; THIOPERAMIDE; UNCLASSIFIED DRUG; HISTAMINE H3 RECEPTOR ANTAGONIST; LIGAND;

ANIMAL EXPERIMENT; ANTICONVULSANT ACTIVITY; ANTICONVULSANT THERAPY; ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; CONVULSION; DISEASE DURATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; LATENT PERIOD; MALE; MYOCLONUS; NONHUMAN; RAT; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CHO CELL LINE; CRICETULUS; DOSE RESPONSE; HEK293 CELL LINE; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; WISTAR RAT;

ANIMALS; ANTICONVULSANTS; CHO CELLS; CRICETULUS; DOSE-RESPONSE RELATIONSHIP, DRUG; HEK293 CELLS; HISTAMINE H3 ANTAGONISTS; HUMANS; LIGANDS; MALE; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; RECEPTORS, HISTAMINE H3; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84896521356     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.014     Document Type: Article

References (49)

1. M.L. Scheurer, T.A. Pedley, The evaluation and treatment of seizures, New England Journal of Medicine 323 (1990) 1468-1474. (Pubitemid 20384956)
2. W. Löscher, H. Klitgaard, R.E. Twyman, D. Schmidt, New avenues for anti-epileptic drug discovery and development, Nature Reviews Drug Discovery 12 (2013) 757-776.
3. S. Malik, R.S. Bahare, S.A. Khan, Design, synthesis and anticonvulsant evaluation of N-(benzo[d]thiazol-2-ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)- carbothioamide derivatives: a hybrid pharmacophore approach, European Journal of Medicinal Chemistry 67 (2013) 1-13.
4. K.A. Wesnes, C. Edgar, A.D. Dean, S.J. Wroe, The cognitive and psychomotor effects of remacemide and carbamazepine in newly diagnosed epilepsy, Epilepsy & behavior 14 (2009) 522-528.
5. K.J.J. Meador, Newer anticonvulsants: dosing strategies and cognition in treating patients with mood disorders and epilepsy, Clin. Psychiatry 64 (2003) 30-34.
6. H. Stefan, T. Feuerstein, Novel anticonvulsant drugs, Pharmacology & Therapeutics 113 (2007) 165-183. (Pubitemid 46017070)
7. F. Bilotta, A.W. Gelb, E. Stazi, L. Titi, F.P. Paoloni, G. Rosa, Pharmacological perioperative brain neuroprotection: a qualitative review of randomized clinical trials, British Journal of Anaesthesia 110 (2013 Jun) (Epub 2013 Apr 5).
8. P.L. Chazot, Safinamide for the treatment of Parkinson's disease, epilepsy and restless legs syndrome, Current Opinion in Investigational Drugs 8 (2013) 570-579.
9. L.S. Zhang, Z. Chen, Y.W. Huang, W.W. Hu, E.Q. Wei, K. Yanai, Effects of endogenous histamine on seizure development of pentylenetetrazoleinduced kindling in rats, Pharmacology 69 (2003) 27-32. (Pubitemid 36928720)
10. C. Kamei, K. Ishizawa, H. Kakinoki, M. Fukunaga, Histaminergic mechanisms in amygdaloid-kindled seizures in rats, Epilepsy Research 30 (1998) 187-194. (Pubitemid 28273383)
11. Z. Chen, W.D. Li, L.J. Zhu, Y.J. Shen, E.Q. Wei, Effects of histidine, a precursor of histamine, on pentylenetetrazole-induced seizures in rats, Acta Pharmacologica Sinica 23 (2002) 361-366. (Pubitemid 34266596)
12. T. Hirai, C. Okuma, C. Harada, M. Mio, H. Ohtsu, T. Watanabe, Development of amygdaloid kindling in histidine decarboxylaseedeficient and histamine H1 receptoredeficient mice, Epilepsia 45 (2004) 309-313. (Pubitemid 38489983)
13. K. Iinuma, H. Yokoyama, T. Otsuki, K. Yanai, T. Watanabe, T. Ido, Histamine H1 receptors in complex partial seizure, Lancet 341 (1993) 238. (Pubitemid 23048107)
14. I. Miyata, H. Saegusa, M. Sakurai, Seizure-modifying potential of histamine H1 antagonists: a clinical observation, Pediatrics International 53 (2011) 706-708.
15. D.H. Jang, A.F. Manini, N.S. Trueger, D. Duque, N.B. Nestor, L.S. Nelson, Status epilepticus and wide-complex tachycardia secondary to diphenhydramine overdose, Clinical Toxicology (Philadelphia, PA) 48 (2010) 945-948.
16. Y. Shimoda, A. Koizumi, K. Tanaka, Electroencephalographic activation of "diencephalic epilepsy" with diphenhydrami, Yonago Acta Medica 4 (1960) 99-102.
17. D. Singh, R.K. Goel, Proconvulsant potential of cyproheptadine in experimental animal models, Fundamental & clinical Pharmacology 24 (2010) 451-455.
18. 3R) antagonist pitolisant (formerly known as tiprolisant; BF2.649) in epilepsy: dose-dependent effects in the human photosensitivity model, Epilepsy & Behavior 28 (2013) 66-70.
19. Bioprojet: Raga, M.M., Sallares, J., Guerrero, M., Guglietta, A., Arrang, J.-M., Schwartz, J.-C., Lecomte, J.-M., Ligneau, X., Schunack, W., Ganellin, C. R., Stark, H., 2006. Patent WO2006084833A1.
20. R. Morphy, C. Kay, Z. Rankovic, From magic bullets to designed multiple ligands, Drug Discovery Today 9 (2004) 641-651. (Pubitemid 38981718)
21. C.J. Van der Schyf, W.J. Geldenhuys, M.B.H. Youdim, Multifunctional drugs with different CNS targets for neuropsychiatric disorders, Journal of Neurochemistry 99 (2006) 1033-1048. (Pubitemid 44655271)
22. Y. von Coburg, T. Kottke, L. Weizel, X. Ligneau, H. Stark, Potential utility of histamine H3 receptor antagonist pharmacophore in antipsychotics, Bioorganic & Medicinal Chemistry Letters 19 (2009) 538-542.
23. J.M. Keith, L.A. Gomez, M.A. Letavic, K.S. Ly, J.A. Jablonowski, M. Seierstad, A.J. Barbier, S.J. Wilson, J.D. Boggs, I.C. Fraser, C. Mazur, T.W. Lovenberg, N.I. Carruthers, Dual serotonin transporter/histamine H3 ligands: optimization of the H3 pharmacophore, Bioorganic & Medicinal Chemistry Letters 17 (2007) 702-706. (Pubitemid 46108568)
24. R.J. Altenbach, L.A. Black, M.I. Strakhova, A.M. Manelli, T.L. Carr, K.C. Marsh, J.M. Wetter, E.J. Wensink, G.C. Hsieh, P. Honore, T.R. Garrison, J.D. Brioni, M.D. Cowart, Diaryldiamines with dual inhibition of the histamine H(3) receptor and the norepinephrine transporter and the efficacy of 4-(3-(methyl-amino)-1-phenylpropyl)-6-(2-(pyrrolidin-1-yl)ethoxy) naphthalen-1-ol in pain, Journal of Medicinal Chemistry 53 (2010) 7869-7873.
25. H. Biltz, Über die Konstitution der Einwirkungsprodukte von substituierten Harnstoffen auf Benzil und über einige neue Methoden zur Darstellung der 5.5-Diphenyl-hydantoine (New preparation methods of 5.5 Diphenylhydantoin with substituted urea and benzil), Chemische Berichte 41 (1908) 1379-1393.
26. M.J. Stocks, D.R. Cheshire, R. Reynolds, Efficient and regiospecific one-pot synthesis of substituted 1,2,4-triazoles, Organic Letters 6 (2004) 2969-2971. (Pubitemid 39178052)
27. K. Isensee, M. Amon, A. Galaparti, X. Ligneau, J.C. Camelin, M. Capet, J.C. Schwartz, H. Stark, Fluorinated non-imidazole histamine H3 receptor antagonists, Bioorganic & Medicinal Chemistry Letters 19 (2009) 2172-2175.
28. G. Meier, J. Apelt, U. Reichert, S. Grassmann, X. Ligneau, S. Elz, F. Leurquin, C.R. Ganellin, J.C. Schwartz, W. Schunack, H. Stark, Influence of imidazole replacement in different structural classes of histamine H(3)-receptor antagonists, European Journal of Pharmaceutical Sciences 13 (2001) 249-259. (Pubitemid 32522577)
29. (a) M. Tomasch, J.S. Schwed, A. Paulke, H. Stark, Bodilisant - a novel fluorescent, highly affine histamine H3 receptor ligand, ACS Medicinal Chemistry Letters 4 (2013) 269-273;
30. (b) M. Amon, X. Ligneau, J.C. Camelin, I. Berrebi-Bertrand, J.C. Schwartz, H. Stark, Highly potent fluorescence-tagged nonimidazole histamine H3 receptor ligands, ChemMedChem 2 (2007) 708-716.
31. A. Williamson, About the theory of the formation of ethers, Justus Liebigs Ann. Chem. 77 (1851) 37-49.
32. H. Finkelstein, Darstellung organischer Jodide aus den entsprechenden Bromiden und Chloriden, Berichte der Deutschen Chemischen Gesellschaft 43 (1910) 1528-1532.
33. R. Seifert, A. Strasser, E.H. Schneider, D. Neumann, S. Dove, A. Buschauer, Molecular and cellular analysis of human histamine receptor subtypes, Trends in Pharmacological Sciences 34 (2013) 33-58.
34. A. Strasser, H.J. Wittmann, A. Buschauer, E.H. Schneider, R. Seifert, Speciesdependent activities of G-protein-coupled receptor ligands: lessons from histamine receptor orthologs, Trends in Pharmacological Sciences 34 (2013) 13-32.
35. T. Curtius, H. Franzen, Darstellung von Säurehydraziden aus Diammoniumsalzen (Preparation of acid hydrazides from diammonium salts), Chemische Berichte 35 (1902) 3239-3241.
36. K.M. Khan, M. Rasheed, U. Zia, S. Hayat, F. Kaukab, M.I. Choudhary, A. urRahman, S. Perveen, Synthesis and in vitro leishmanicidal activity of some hydrazides and their analogues, Bioorganic & Medicinal Chemistry 11 (2003) 1381-1387. (Pubitemid 36293532)
37. M. Walter, Y. von Coburg, K. Isensee, K. Sander, X. Ligneau, J.-C. Camelin, J.-C. Schwartz, H. Stark, Azole derivatives as histamine H3 receptor antagonists, part 2: C-C and C-S coupled heterocycles, Bioorganic & Medicinal Chemistry Letters 20 (2010) 5883-5886.
38. K. Sander, T. Kottke, L. Weizel, H. Stark, Kojic acid derivatives as histamine H3 receptor ligands, Chemical & Pharmaceutical Bulletin (Tokyo) 58 (2010) 1353-1361.
39. K. Sander, T. Kottke, C. Hoffend, M. Walter, L. Weizel, J.C. Camelin, X. Ligneau, E.H. Schneider, R. Seifert, J.C. Schwartz, H. Stark, First metal-containing histamine H3 receptor ligands, Organic Letters 12 (2012) 2578-2581.
40. X. Ligneau, D. Perrin, L. Landais, J.C. Camelin, T.P. Calmels, I. Berrebi-Bertrand, J.M. Lecomte, R. Parmentier, C. Anaclet, J.S. Lin, V. Bertaina-Anglade, C.D. la Rochelle, F. d'Aniello, A. Rouleau, F. Gbahou, J.M. Arrang, C.R. Ganellin, H. Stark, W. Schunack, J.C. Schwartz, BF2.649 [1-{3-[3-(4-Chlorophenyl)propoxy]propyl}piperidine, hydrochloride], a nonimidazole inverse agonist/antagonist at the human histamine H3 receptor: preclinical pharmacology, Journal of Pharmacology and Experimental Therapeutics 320 (2007) 365-375. (Pubitemid 46025751)
41. Y.C. Cheng, W.H. Prusoff, Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction, Biochemical Pharmacology 22 (1973) 3099-3108.
42. (a) K. Schlotter, F. Boeckler, H. Hubner, P. Gmeiner, Fancy bioisosteres: metallocene-derived G-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles, Journal of Medicinal Chemistry 48 (2005) 3696-3699;
43. (b) M.F.R. Fouda, M.M. Abd-Elzaher, R.A. Abdelsamaia, A.A. Labib, On the medicinal chemistry of ferrocene, Applied Organometallic Chemistry 21 (2007) 613-625;
44. (c) D.R. van Staveren, N. Metzler-Nolte, Bioorganometallic chemistry of ferrocene, Chemical Reviews 104 (2004) 5931-5985;
45. (d) R. Schibli, P.A. Schubiger, Current use and future potential of organometallic radiopharmaceuticals, European Journal of Nuclear Medicine and Molecular Imaging 29 (2002) 1529-1542.
46. B. Sadek, S. Shehab, M. Wiecek, S. Dhanasekaran, M. Shafiullah, K. Kieć-Kononowicz, A. Adem, Anticonvulsant properties of histamine H3 receptor ligands belonging to N-substituted carbamates of imidazopropanol, Bioorganic & Medicinal Chemistry Letters 23 (2013) 4886-4891.
47. K.H. Reeta, J. Mehla, M. Pahuja, Y.K. Gupta, Pharmacokinetic and pharmacodynamic interactions of valproate, phenytoin, phenobarbitone and carbamazepine with curcumin in experimental models of epilepsy in rats, Pharmacology Biochemistry and Behavior 99 (2011) 399-407.
48. G.M. Keserü, G.M. Makara, The influence of lead discovery strategies on the properties of drug candidates, Nature Reviews Drug Discovery 8 (2009) 203-312.
49. W. Loescher, Critical review of current animal models of seizures and epilepsy used in the discovery and development of new antiepileptic drugs, Seizure 20 (2011) 359-368.