SAR-studies on the importance of aromatic ring topologies in search for selective 5-HT7 receptor ligands among phenylpiperazine hydantoin derivatives

European Journal of Medicinal Chemistry

Volumn 78, Issue , 2014, Pages 324-339

  Handzlik, Jadwiga ^a   Bojarski, Andrzej J ^b   Satała, Grzegorz ^b   Kubacka, Monika ^a   Sadek, Bassem ^c   Ashoor, Abrar ^c   Siwek, Agata ^a   Wiȩcek, Małgorzata ^a   Kucwaj, Katarzyna ^a   Filipek, Barbara ^a   Kieć Kononowicz, Katarzyna ^a  

^a JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

^b INSTITUTE OF PHARMACOLOGY   (Poland)

^c UNITED ARAB EMIRATES UNIVERSITY   (United Arab Emirates)

Author keywords

Alpha1 adrenoceptor; Hydantoins; Mitsunobu reaction; Phenylpiperazines

Indexed keywords

1 METHYL 3 INDAZOLECARBOXYLIC ACID N TROPANYLAMIDE; 5 [ 4 FLUOROPHENYL] 3 [ HYDROXY 3 [ 4 ( 2 METHOXYPHENYL)PIPERAZIN 1 YL]PROPYL] 5 METHYLIMIDAZOLIDINE 2,4 DIONE; ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 1D ADRENERGIC RECEPTOR; AROMATIC COMPOUND; BUSPIRONE; CLOZAPINE; HYDANTOIN DERIVATIVE; OLANZAPINE; PHENTOLAMINE; RADIOLIGAND; SEROTONIN 1A RECEPTOR; SEROTONIN 3A RECEPTOR; SEROTONIN 6 RECEPTOR; SEROTONIN 7 RECEPTOR; SEROTONIN ANTAGONIST; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG; LIGAND; PHENYLPIPERAZINE; PIPERAZINE DERIVATIVE;

ALKYLATION; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL STRAIN HEK293; CONTROLLED STUDY; DRUG EFFECT; DRUG INHIBITION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MITSUNOBU REACTION; NONHUMAN; OOCYTE; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN LOCALIZATION; RADIOASSAY; RING OPENING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; XENOPUS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; METABOLISM; SYNTHESIS;

DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; HYDANTOINS; LIGANDS; MOLECULAR STRUCTURE; PIPERAZINES; RECEPTORS, SEROTONIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84897397587     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.01.065     Document Type: Article

References (32)

1. Y.B. Lee, Y.D. Gong, D.J. Kim, C.H. Ahn, J.Y. Kong, and N.S. Kang Synthesis, anticancer activity and pharmacokinetic analysis of 1-[(substituted 2-alkoxyquinoxalin-3-yl)aminocarbonyl]-4-(hetero)arylpiperazine derivatives Bioorganic & Medicinal Chemistry 20 2012 1303 1309
2. A. Blaser, B.D. Palmer, H.S. Sutherland, I. Kmentova, S.G. Franzblau, B. Wan, Y. Wang, Z. Ma, A.M. Thompson, and W.A. Denny Structure-activity relationships for amide-, carbamate- and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro- 5H-imidazo[2,1-b][1,3]oxazine Journal of Medicinal Chemistry 55 2012 312 326
3. 1-adrenoceptor affinities Bioorganic & Medicinal Chemistry 20 2012 2290 2303
4. J. Handzlik, E. Szymańska, J. Chevalier, E. Otrȩbska, K. Kieć-Kononowicz, J.-M. Pagès, and S. Alibert Amine-alkyl derivatives of hydantoin: new tool to combat resistant bacteria European Journal of Medicinal Chemistry 46 2011 5807 5816
5. G. Spengler, M. Evaristo, J. Handzlik, J. Serly, J. Molnár, M. Viveiros, K. Kieć-Kononowicz, and L. Amaral Biological activity of hydantoin derivatives on p-glycoprotein (ABCB1) of mouse lymphoma cells Anticancer Research 30 2010 4867 4871
6. G. Spengler, J. Handzlik, I. Ocsovszki, M. Viveiros, K. Kieć-Kononowicz, J. Molnar, and L. Amaral Modulation of multidrug efflux pump activity by new hydantoin derivatives on colon adenocarcinoma cells without inducing apoptosis Anticancer Research 31 2011 3285 3288
7. J. Handzlik, E. Szymańska, S. Alibert, J. Chevalier, E. Otrȩbska, E. Pȩkala, J.-M. Pagès, and K. Kieć-Kononowicz Search for new tools to combat gram-negative resistant bacteria among amine derivatives of 5-arylidenehydantoin Bioorganic & Medicinal Chemistry 21 2013 135 145
8. R. Romagnoli, P.G. Baraldi, M.D. Carrion, C.L. Cara, O. Cruz-Lopez, M.K. Salvador, D. Preti, M.A. Tabrizi, A.R. Moorman, F. Vincenzi, P.A. Borea, and K. Varani Synthesis and biological evaluation of 2-amino-3-(4-chlorobenzoyl)-4-[(4- arylpiperazin-1-yl)methyl]-5-substituted-thiophenes. effect of the 5-modification on allosteric enhancer activity at the A1 adenosine receptor Journal of Medicinal Chemistry 55 2012 7719 7735
9. D. Ignjatović, D. Vojnović Milutinović, A. Nikolić-Kokić, M. Slavić, D. Andrić, M. Tomić, and S. Kostić-Rajačić The mechanisms responsible for neuroprotective capacity of arylpiperazine dopaminergic ligands against cell death induced by sodium nitroprusside European Journal of Pharmacology 683 2012 93 100
10. P. Zajdel, K. Marciniec, A. Maślankiewicz, G. Satała, B. Duszyńska, A.J. Bojarski, A. Partyka, M. Jastrzȩbska- Wiȩsek, D. Wróbel, A. Wesołowska, and M. Pawłowski Quinoline- and isoquinoline-sulfonamide derivatives of LCAP as potent CNS multi-receptor - 5-HT1A/5-HT2A/5-HT7 and D2/D3/D4 - agents: the synthesis and pharmacological evaluation Bioorganic & Medicinal Chemistry 20 2012 1545 1556
11. 7 receptor agents: structure-activity relationships and potential therapeutic applications in central nervous system disorders Pharmacology & Therapeutics 129 2011 120 148
12. 1-adrenoceptor antagonistic properties Bioorganic & Medicinal Chemistry 20 2012 4245 4257
13. M.L. López-Rodríguez, D. Ayala, B. Benhamú, M.J. Morcillo, and A. Viso Arylpiperazine derivatives acting at 5-HT(1A) receptors Current Medicinal Chemistry 9 2002 443 469
14. 7 receptor ligands Bioorganic & Medicinal Chemistry 19 2011 6750 6759
15. 7 receptor antagonists Bioorganic & Medicinal Chemistry 16 2008 5405 5412
16. J.H. Bremner, B. Coban, R. Griffith, K.M. Groenewoud, and B.F. Yates Ligand design for alpha1 adrenoceptor subtype selective antagonists Bioorganic & Medicinal Chemistry 8 2000 201 214
17. L. Du, and M. Li Modeling the interactions between alpha(1)-adrenergic receptors and their antagonists Current Computer-Aided Drug Design 6 2010 165 178
18. G. Romeo, L. Materia, M.N. Modica, V. Pittalà, L. Salerno, M.A. Siracusa, F. Manetti, M. Botta, and K.P. Minneman Novel 4-phenylpiperidine-2,6- dione derivatives. Ligands for-adrenoceptor subtypes European Journal of Medicinal Chemistry 46 2011 2676 2690
19. 1-adrenoceptor subtypes for phenylpiperazine derivatives of phenytoin Bioorganic & Medicinal Chemistry Letters 20 2010 6152 6156
20. 6 receptors Bioorganic & Medicinal Chemistry 19 2011 5255 5259
21. S. Yoshida, T. Watanabe, and Y. Sato Regulatory molecules for the 5-HT3 receptor ion channel gating system Bioorganic & Medicinal Chemistry 15 2007 3515 3523
22. R. Barbaro, L. Betti, M. Botta, F. Corelli, G. Giannaccini, L. Maccari, F. Manetti, G. Strappaghetti, and S. Corsano Synthesis, biological evaluation, and pharmacophore generation of new pyridazinone derivatives with affinity toward alpha(1)- and alpha(2)-adrenoceptors Journal of Medicinal Chemistry 44 2001 2118 2132
23. A.J. Bojarski Pharmacophore models for metabotropic 5-HT receptor ligands Current Topics in Medicinal Chemistry 6 2006 2005 2026
24. A. Lepailleur, R. Bureau, M. Paillet-Loilier, F. Fabis, N. Saettel, S. Lemaitre, F. Dauphin, A. Lesnard, J.-Ch Lancelot, and S. Rault Molecular modeling studies focused on 5-HT7 versus 5-HT1A selectivity. Discovery of novel phenylpyrrole derivatives with high affinity for 5-HT7 receptors Journal of Chemical Information and Modeling 45 2005 1075 1081
25. 1-adrenergic receptors among arylpiperazine derivatives of phenytoin Bioorganic & Medicinal Chemistry 19 2011 1349 1360
26. 1- adrenoceptor antagonist activity and SAR-study for novel arylpiperazine derivatives of phenytoin Bioorganic & Medicinal Chemistry 16 2008 5982 5998
27. W.G. Lachnit, A.M. Tran, D.E. Clarke, and A.P. Ford Pharmacological characterization of an alpha 1A-adrenoceptor mediating contractile responses to noradrenaline in isolated caudal artery of rat British Journal of Pharmacology 120 1997 819 826
28. S. Jähnichen, M. Eltze, and H.H. Pertz Evidence that alpha(1B)-adrenoceptors are involved in noradrenaline-induced contractions of rat tail artery European Journal of Pharmacology 488 2004 157 167
29. M. Eltze, R. Boer, M.C. Michel, P. Hein, R. Testa, W.R. Ulrich, N. Kolassa, and K.H. Sanders In vitro and in vivo uroselectivity of B8805-033, an antagonist with high affinity at prostatic alpha1A- vs. alpha1B- and alpha1D-adrenoceptors Naunyn-Schmiedeberg's Archives of Pharmacology 363 2001 649 662
30. Y. Cheng, and W. 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
31. 3 receptor-mediated responses in Xenopus oocytes Synapse 46 2002 150 156
32. 2+ sensors Molecular Pharmacology 54 1998 1106 1112