메뉴 건너뛰기




Volumn 57, Issue 7, 2014, Pages 2884-2894

Synthesis, pharmacological evaluation, and σ1 receptor interaction analysis of hydroxyethyl substituted piperazines

Author keywords

[No Author keywords available]

Indexed keywords

(S)2 [4 (CYCLOHEXYLMETHYL) 1 (NAPHTHALEN 2 YLMETHYL)PIPERAZIN 2 YL]ETHANOL; (S)METHYL 2 [4 (CYCLOHEXYLMETHYL) 1 (NAPHTHALEN 2 YLMETHYL) 3,6 DIOXO PIPERAZIN 2 YL]ACETATE; ASPARTIC ACID; CHEMICAL COMPOUND; DIMETHYL(S) 2 AMINOBUTANEDIOATE HYDROCHLORIDE; DIMETHYL(S) 2 [2 CHLORO N(NAPHTHALEN 2 YLMETHYL)ACETYLAMINO]BUTANEDIOATE; HYDROXYETHYL; PIPERAZINE DERIVATIVE; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG;

EID: 84898444903     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm401707t     Document Type: Article
Times cited : (16)

References (55)
  • 1
    • 0141610329 scopus 로고
    • Naloxone-inaccessible σ receptor in rat central nervous system
    • Tam, S. W. Naloxone-inaccessible σ receptor in rat central nervous system Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 6703-6707
    • (1983) Proc. Natl. Acad. Sci. U.S.A. , vol.80 , pp. 6703-6707
    • Tam, S.W.1
  • 2
    • 0020619765 scopus 로고
    • Naltrexone fails to antagonize the σ effects of PCP and SKF 10,047 in the dog
    • Vaupel, D. B. Naltrexone fails to antagonize the σ effects of PCP and SKF 10,047 in the dog Eur. J. Pharmacol. 1983, 92, 269-274
    • (1983) Eur. J. Pharmacol. , vol.92 , pp. 269-274
    • Vaupel, D.B.1
  • 3
    • 0028180570 scopus 로고
    • Rat liver and kidney contain high densities of sigma 1 and sigma 2 receptors: Characterization by ligand binding and photoaffinity labeling
    • Hellewell, S. B.; Bruce, A.; Feinstein, G.; Orringer, J.; Williams, W.; Bowen, W. D. Rat liver and kidney contain high densities of sigma 1 and sigma 2 receptors: characterization by ligand binding and photoaffinity labeling Eur. J. Pharmacol. 1994, 268, 9-18
    • (1994) Eur. J. Pharmacol. , vol.268 , pp. 9-18
    • Hellewell, S.B.1    Bruce, A.2    Feinstein, G.3    Orringer, J.4    Williams, W.5    Bowen, W.D.6
  • 8
    • 57749085501 scopus 로고    scopus 로고
    • PGRMC1 (progesterone receptor membrane component 1): A targetable protein with multiple functions in steroid signaling, P450 activation and drug binding
    • Rohe, H. J.; Ahmed, I. S.; Twist, K. E.; Craven, R. J. PGRMC1 (progesterone receptor membrane component 1): A targetable protein with multiple functions in steroid signaling, P450 activation and drug binding Pharmacol ther. 2009, 121, 14-19
    • (2009) Pharmacol ther. , vol.121 , pp. 14-19
    • Rohe, H.J.1    Ahmed, I.S.2    Twist, K.E.3    Craven, R.J.4
  • 10
    • 0034680912 scopus 로고    scopus 로고
    • 1 receptor is not directly coupled to G proteins
    • 1 receptor is not directly coupled to G proteins Eur. J. Pharmacol. 2000, 408, 117-125
    • (2000) Eur. J. Pharmacol. , vol.408 , pp. 117-125
    • Hong, W.1    Werling, L.L.2
  • 11
    • 0034053453 scopus 로고    scopus 로고
    • Modulation of cellular calcium by sigma-2 receptors: Release from intracellular stores in human SK-N-SH neuroblastoma cells
    • Vilner, B. J.; Bowen, W. D. Modulation of cellular calcium by sigma-2 receptors: release from intracellular stores in human SK-N-SH neuroblastoma cells J. Pharm. Exp ther. 2000, 292, 900-911
    • (2000) J. Pharm. Exp ther. , vol.292 , pp. 900-911
    • Vilner, B.J.1    Bowen, W.D.2
  • 12
    • 0028795145 scopus 로고
    • Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines
    • Vilner, B. J.; John, C. S.; Bowen, W. D. Sigma-1 and sigma-2 receptors are expressed in a wide variety of human and rodent tumor cell lines Cancer Res. 1995, 55, 408-413
    • (1995) Cancer Res. , vol.55 , pp. 408-413
    • Vilner, B.J.1    John, C.S.2    Bowen, W.D.3
  • 14
    • 33748291765 scopus 로고    scopus 로고
    • Cyclohexylpiperazine derivative PB28, a sigma2 agonist and sigma1 antagonist receptor, inhibits cell growth, modulates p-glycoprotein, and synergizes with antracyclines in breast cancer
    • Azzariti, A.; Colabufo, N. A.; Berardi, F.; Porcelli, L.; Niso, M.; Simone, G. M.; Perrone, R.; Paradiso, A. Cyclohexylpiperazine derivative PB28, a sigma2 agonist and sigma1 antagonist receptor, inhibits cell growth, modulates p-glycoprotein, and synergizes with antracyclines in breast cancer Mol. Cancer Ther. 2006, 5, 1807-1816
    • (2006) Mol. Cancer Ther. , vol.5 , pp. 1807-1816
    • Azzariti, A.1    Colabufo, N.A.2    Berardi, F.3    Porcelli, L.4    Niso, M.5    Simone, G.M.6    Perrone, R.7    Paradiso, A.8
  • 15
    • 84885149491 scopus 로고    scopus 로고
    • Homologous piperazine-alcanols: Chiral pool synthesis and pharmacological evaluation
    • Holl, R.; Schepmann, D.; Wünsch, B. Homologous piperazine-alcanols: chiral pool synthesis and pharmacological evaluation Med. Chem. Commun. 2012, 3, 673-679
    • (2012) Med. Chem. Commun. , vol.3 , pp. 673-679
    • Holl, R.1    Schepmann, D.2    Wünsch, B.3
  • 17
    • 0027078540 scopus 로고
    • Characterization of the binding of [3H]-(+)-pentazocine to σ recognition sites in guinea pig brain
    • De Haven Hudkins, D. L.; Fleissner, L. C.; Ford-Rice, F. Y. Characterization of the binding of [3H]-(+)-pentazocine to σ recognition sites in guinea pig brain Eur. J. Pharmacol. 1992, 227, 371-378
    • (1992) Eur. J. Pharmacol. , vol.227 , pp. 371-378
    • De Haven Hudkins, D.L.1    Fleissner, L.C.2    Ford-Rice, F.Y.3
  • 18
    • 84865521227 scopus 로고    scopus 로고
    • Characterization of ligand binding to the σ1 receptor in a human tumor cell line (RPMI 8226) and establishment of a competitive receptor binding assay
    • Brune, S.; Schepmann, D.; Lehmkuhl, K.; Frehland, B.; Wünsch, B. Characterization of ligand binding to the σ1 receptor in a human tumor cell line (RPMI 8226) and establishment of a competitive receptor binding assay Assay Drug Dev. Technol. 2012, 10, 365-374
    • (2012) Assay Drug Dev. Technol. , vol.10 , pp. 365-374
    • Brune, S.1    Schepmann, D.2    Lehmkuhl, K.3    Frehland, B.4    Wünsch, B.5
  • 19
    • 79956138579 scopus 로고    scopus 로고
    • Expression of sigma receptors of human urinary bladder tumor cells (RT-4 cells) and development of a competitive receptor binding assay for the determination of ligand affinity to human sigma2 receptors
    • Schepmann, D.; Lehmkuhl, K.; Brune, S.; Wünsch, B. Expression of sigma receptors of human urinary bladder tumor cells (RT-4 cells) and development of a competitive receptor binding assay for the determination of ligand affinity to human sigma2 receptors J. Pharm. Biomed. Anal. 2011, 55, 1136-1141
    • (2011) J. Pharm. Biomed. Anal. , vol.55 , pp. 1136-1141
    • Schepmann, D.1    Lehmkuhl, K.2    Brune, S.3    Wünsch, B.4
  • 21
    • 84891495609 scopus 로고    scopus 로고
    • Involvement of apoptosis and autophagy in the death of RPMI 8226 multiple myeloma cells by two enantiomeric sigma receptor ligands
    • Korpis, K.; Weber, F.; Brune, S.; Wünsch, B.; Bednarski, P. J. Involvement of apoptosis and autophagy in the death of RPMI 8226 multiple myeloma cells by two enantiomeric sigma receptor ligands Bioorg. Med. Chem. 2014, 22, 221-233
    • (2014) Bioorg. Med. Chem. , vol.22 , pp. 221-233
    • Korpis, K.1    Weber, F.2    Brune, S.3    Wünsch, B.4    Bednarski, P.J.5
  • 23
    • 84868585563 scopus 로고    scopus 로고
    • Another brick in the wall. Validation of the σ1 receptor 3D model by computer-assisted design, synthesis, and activity of new σ1 ligands
    • Laurini, E.; Marson, D.; Dal Col, V.; Fermeglia, M.; Mamolo, M. G.; Zampieri, D.; Vio, L.; Pricl, S. Another brick in the wall. Validation of the σ1 receptor 3D model by computer-assisted design, synthesis, and activity of new σ1 ligands Mol. Pharmaceutics 2012, 9, 3107-3126
    • (2012) Mol. Pharmaceutics , vol.9 , pp. 3107-3126
    • Laurini, E.1    Marson, D.2    Dal Col, V.3    Fermeglia, M.4    Mamolo, M.G.5    Zampieri, D.6    Vio, L.7    Pricl, S.8
  • 24
    • 84866856929 scopus 로고    scopus 로고
    • Pd-catalyzed direct C-H bond functionalization of spirocyclic sigma-1 ligands: Generation of a pharmacophore model and analysis of reverse binding mode by docking into a 3D homology model of the sigma-1 receptor
    • Meyer, C.; Schepmann, D.; Yanagisawa, S.; Yamaguchi, J.; Dal Col, V.; Laurini, E.; Itami, K.; Pricl, S.; Wünsch, B. Pd-catalyzed direct C-H bond functionalization of spirocyclic sigma-1 ligands: generation of a pharmacophore model and analysis of reverse binding mode by docking into a 3D homology model of the sigma-1 receptor J. Med. Chem. 2012, 55, 8047-8065
    • (2012) J. Med. Chem. , vol.55 , pp. 8047-8065
    • Meyer, C.1    Schepmann, D.2    Yanagisawa, S.3    Yamaguchi, J.4    Dal Col, V.5    Laurini, E.6    Itami, K.7    Pricl, S.8    Wünsch, B.9
  • 28
    • 35048894323 scopus 로고    scopus 로고
    • Synthesis, antifungal and antimycobacterial activities of new bis-imidazole derivatives, and prediction of their binding to P450(14DM) by molecular docking and MM/PBSA method
    • Zampieri, D.; Mamolo, M. G.; Vio, L.; Banfi, E.; Scialino, G.; Fermeglia, M.; Ferrone, M.; Pricl, S. Synthesis, antifungal and antimycobacterial activities of new bis-imidazole derivatives, and prediction of their binding to P450(14DM) by molecular docking and MM/PBSA method Bioorg. Med. Chem. 2007, 15, 7444-7458
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 7444-7458
    • Zampieri, D.1    Mamolo, M.G.2    Vio, L.3    Banfi, E.4    Scialino, G.5    Fermeglia, M.6    Ferrone, M.7    Pricl, S.8
  • 29
    • 33846708825 scopus 로고    scopus 로고
    • Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenanthrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses
    • Carta, A.; Loriga, M.; Paglietti, G.; Ferrone, M.; Fermeglia, M.; Pricl, S.; Sanna, T.; Ibba, C.; La Colla, P.; Loddo, R. Design, synthesis, and preliminary in vitro and in silico antiviral activity of [4,7]phenanthrolines and 1-oxo-1,4-dihydro-[4,7]phenantrolines against single-stranded positive-sense RNA genome viruses Bioorg. Med. Chem. 2007, 15, 1914-1927
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 1914-1927
    • Carta, A.1    Loriga, M.2    Paglietti, G.3    Ferrone, M.4    Fermeglia, M.5    Pricl, S.6    Sanna, T.7    Ibba, C.8    La Colla, P.9    Loddo, R.10
  • 32
    • 0142227149 scopus 로고    scopus 로고
    • Studying enzyme enantioselectivity using combined ab initio and free energy calculations: Alfa-chymotrypsin and methyl cis- and trans-5-oxo-2- pentylpirrolidine-3-carboxylates
    • Felluga, F.; Pitacco, G.; Valentin, E.; Coslanich, A.; Fermeglia, M.; Ferrone, M.; Pricl, S. Studying enzyme enantioselectivity using combined ab initio and free energy calculations: alfa-chymotrypsin and methyl cis- and trans-5-oxo-2-pentylpirrolidine-3-carboxylates Tetrahedron: Asymmetry 2003, 14, 3385-3399
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 3385-3399
    • Felluga, F.1    Pitacco, G.2    Valentin, E.3    Coslanich, A.4    Fermeglia, M.5    Ferrone, M.6    Pricl, S.7
  • 35
    • 3042524904 scopus 로고
    • A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: The RESP model
    • Bayly, C. I.; Cieplak, P.; Cornell, W.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model J. Phys. Chem. 1993, 97, 10269-10280
    • (1993) J. Phys. Chem. , vol.97 , pp. 10269-10280
    • Bayly, C.I.1    Cieplak, P.2    Cornell, W.3    Kollman, P.A.4
  • 36
    • 0000667030 scopus 로고
    • Application of the RESP charges to calculate conformational energies, hydrogen bond energies, and free energies of solvatation
    • Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Kollman, P. A. Application of the RESP charges to calculate conformational energies, hydrogen bond energies, and free energies of solvatation J. Am. Chem. Soc. 1993, 115, 9620-9631
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9620-9631
    • Cornell, W.D.1    Cieplak, P.2    Bayly, C.I.3    Kollman, P.A.4
  • 37
    • 84986516411 scopus 로고
    • Application of the multimolecule and multiconformational RESP methodology to biopolymers: Charge derication for DNA; RNA, and proteins
    • Cieplak, P.; Cornell, W.; Bayly, C.; Kollman, P. Application of the multimolecule and multiconformational RESP methodology to biopolymers: charge derication for DNA; RNA, and proteins J. Comput. Chem. 1995, 116, 1357-1376
    • (1995) J. Comput. Chem. , vol.116 , pp. 1357-1376
    • Cieplak, P.1    Cornell, W.2    Bayly, C.3    Kollman, P.4
  • 40
    • 0030038849 scopus 로고    scopus 로고
    • Structure, energetics, and dynamics of lipid-protein interactions: A molecular dynamics study of the gramicidin A channel in a DMPC bilayer
    • Woolf, T. B.; Roux, B. Structure, energetics, and dynamics of lipid-protein interactions: A molecular dynamics study of the gramicidin A channel in a DMPC bilayer Proteins 1996, 24, 92-114
    • (1996) Proteins , vol.24 , pp. 92-114
    • Woolf, T.B.1    Roux, B.2
  • 41
    • 41149134824 scopus 로고    scopus 로고
    • Automated builder and database of protein/membrane complexes for molecular dynamics simulations
    • Jo, S.; Kim, T.; Im, W. Automated builder and database of protein/membrane complexes for molecular dynamics simulations PLoS One 2007, 2, 880
    • (2007) PLoS One , vol.2 , pp. 880
    • Jo, S.1    Kim, T.2    Im, W.3
  • 42
    • 68949149548 scopus 로고    scopus 로고
    • CHARMM-GUI membrane builder for mixed bilayers and its application to yeast membranes
    • Jo, S.; Lim, J. B.; Klauda, J. B.; Im, W. CHARMM-GUI membrane builder for mixed bilayers and its application to yeast membranes Biophys. J. 2009, 97, 50-8
    • (2009) Biophys. J. , vol.97 , pp. 50-58
    • Jo, S.1    Lim, J.B.2    Klauda, J.B.3    Im, W.4
  • 43
    • 84866397847 scopus 로고    scopus 로고
    • LIPID11: A Modular framework for lipid simulations using Amber
    • Skjevik, Å. A.; Madej, B.D.; Walker, R. C.; Teigen, K. LIPID11: A Modular framework for lipid simulations using Amber J. Phys. Chem. B. 2012, 116, 11124-36
    • (2012) J. Phys. Chem. B. , vol.116 , pp. 11124-11136
    • Skjevik, Å.A.1    Madej . B, D.2    Walker, R.C.3    Teigen, K.4
  • 45
    • 79957865467 scopus 로고    scopus 로고
    • 2-Difluoromethylene-4-methylenepentanoic acid, A paradoxical probe able to mimic the signaling role of 2-oxoglutaric acid in cyanobacteria
    • Liu, X.; Chen, H.; Laurini, E.; Wang, Y.; Dal Col, V.; Posocco, P.; Ziarelli, F.; Fermeglia, M.; Zhang, C. C.; Pricl, S.; Peng, L. 2-Difluoromethylene-4-methylenepentanoic acid, A paradoxical probe able To mimic the signaling role of 2-oxoglutaric acid in cyanobacteria Org. Lett. 2011, 13, 2924-2927
    • (2011) Org. Lett. , vol.13 , pp. 2924-2927
    • Liu, X.1    Chen, H.2    Laurini, E.3    Wang, Y.4    Dal Col, V.5    Posocco, P.6    Ziarelli, F.7    Fermeglia, M.8    Zhang, C.C.9    Pricl, S.10    Peng, L.11
  • 46
    • 77955473941 scopus 로고    scopus 로고
    • Synergistic experimental/computational studies on arylazoenamine derivatives that target the bovine viral diarrhea virus RNA-dependent RNA polymerase
    • Giliberti, G.; Ibba, C.; Marongiu, E.; Loddo, R.; Tonelli, M.; Boido, V.; Laurini, E.; Posocco, P.; Fermeglia, M.; Pricl, S. Synergistic experimental/computational studies on arylazoenamine derivatives that target the bovine viral diarrhea virus RNA-dependent RNA polymerase Bioorg. Med. Chem. 2010, 18, 6055-6068
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 6055-6068
    • Giliberti, G.1    Ibba, C.2    Marongiu, E.3    Loddo, R.4    Tonelli, M.5    Boido, V.6    Laurini, E.7    Posocco, P.8    Fermeglia, M.9    Pricl, S.10
  • 47
    • 77949273812 scopus 로고    scopus 로고
    • Pharmacophore modeling, resistant mutant isolation, docking, and MM-PBSA analysis: Combined experimental/computer-assisted approaches to identify new inhibitors of the bovine viral diarrhea virus (BVDV)
    • Tonelli, M.; Boido, V.; La Colla, P.; Loddo, R.; Posocco, P.; Paneni, M. S.; Fermeglia, M.; Pricl, S. Pharmacophore modeling, resistant mutant isolation, docking, and MM-PBSA analysis: Combined experimental/computer-assisted approaches to identify new inhibitors of the bovine viral diarrhea virus (BVDV) Bioorg. Med. Chem. 2010, 18, 2304-2316
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 2304-2316
    • Tonelli, M.1    Boido, V.2    La Colla, P.3    Loddo, R.4    Posocco, P.5    Paneni, M.S.6    Fermeglia, M.7    Pricl, S.8
  • 48
    • 70449631074 scopus 로고    scopus 로고
    • Activity and molecular modeling of a new small molecule active against NNRTI-resistant HIV-1 mutants
    • Carta, A.; Pricl, S.; Piras, S.; Fermeglia, M.; La Colla, P.; Loddo, R. Activity and molecular modeling of a new small molecule active against NNRTI-resistant HIV-1 mutants Eur. J. Med. Chem. 2009, 44, 5117-5122
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 5117-5122
    • Carta, A.1    Pricl, S.2    Piras, S.3    Fermeglia, M.4    La Colla, P.5    Loddo, R.6
  • 50
    • 20644449471 scopus 로고    scopus 로고
    • Modification of the generalized born model suitable for macromolecules
    • Onufriev, A.; Bashford, D.; Case, D. A. Modification of the generalized born model suitable for macromolecules J. Phys. Chem. B 2000, 104, 3712-3720
    • (2000) J. Phys. Chem. B , vol.104 , pp. 3712-3720
    • Onufriev, A.1    Bashford, D.2    Case, D.A.3
  • 51
    • 0346971105 scopus 로고    scopus 로고
    • Performance comparison of generalized born and poisson methods in the calculation of electrostatic solvation energies for protein structures
    • Feig, M.; Onufriev, A.; Lee, M. S.; Im, W.; Case, D. A.; Brooks, C. L., III Performance comparison of generalized born and poisson methods in the calculation of electrostatic solvation energies for protein structures J. Comput. Chem. 2004, 25, 265-284
    • (2004) J. Comput. Chem. , vol.25 , pp. 265-284
    • Feig, M.1    Onufriev, A.2    Lee, M.S.3    Im, W.4    Case, D.A.5
  • 53
    • 33646940952 scopus 로고
    • Numerical integration of the cartesian equations of motion of a system with constraints: Molecular dynamics of n-alkanes
    • Ryckaert, J.-P.; Ciccotti, G.; Berendsen, H. J. C. Numerical integration of the cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes J. Comput. Phys. 1977, 23, 327-341
    • (1977) J. Comput. Phys. , vol.23 , pp. 327-341
    • Ryckaert, J.-P.1    Ciccotti, G.2    Berendsen, H.J.C.3
  • 54
    • 0034506266 scopus 로고    scopus 로고
    • Efficient particle-mesh Ewald based approach to fixed and induced dipolar interactions
    • Toukmaji, A.; Sagui, C.; Board, J.; Darden, T. Efficient particle-mesh Ewald based approach to fixed and induced dipolar interactions J. Chem. Phys. 2000, 113, 10913-10927
    • (2000) J. Chem. Phys. , vol.113 , pp. 10913-10927
    • Toukmaji, A.1    Sagui, C.2    Board, J.3    Darden, T.4
  • 55
    • 84898425229 scopus 로고    scopus 로고
    • http://www.esteco.com/home/mode-frontier/mode-frontier.html.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.