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Volumn 25, Issue 11, 2013, Pages 814-822

Studies on the Enantiomers of RC-33 as Neuroprotective Agents: Isolation, Configurational Assignment, and Preliminary Biological Profile

Author keywords

1 receptor agonists; absolute configuration assignment; asymmetric hydrogenation; chemical correlation; enantioselective HPLC; neuroprotective agents

Indexed keywords

1 [3 (1,1' BIPHEN) 4 YL]BUTYL PIPERIDINE; NEUROPROTECTIVE AGENT; OPIATE AGONIST; PIPERIDINE DERIVATIVE; SIGMA 1 OPIATE RECEPTOR; UNCLASSIFIED DRUG;

EID: 84886639929     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22223     Document Type: Article
Times cited : (26)

References (33)
  • 3
    • 84155163741 scopus 로고    scopus 로고
    • A mutation in sigma-1 receptor causes juvenile amyotrophic lateral sclerosis
    • Al-Saif A, Al-Mohanna F, Bohlega S,. A mutation in sigma-1 receptor causes juvenile amyotrophic lateral sclerosis. Ann Neurol 2011; 70: 913-919.
    • (2011) Ann Neurol , vol.70 , pp. 913-919
    • Al-Saif, A.1    Al-Mohanna, F.2    Bohlega, S.3
  • 4
    • 0024400276 scopus 로고
    • Ras-Induced neuronal differentiation of PC12 cells: Possible involvement of fos and jun
    • Sassone-Corsi P, Der CJ, Verma IM,. ras-Induced neuronal differentiation of PC12 cells: possible involvement of fos and jun. Mol Cell Biol 1989; 9: 3174-3183.
    • (1989) Mol Cell Biol , vol.9 , pp. 3174-3183
    • Sassone-Corsi, P.1    Der, C.J.2    Verma, I.M.3
  • 5
    • 0036894824 scopus 로고    scopus 로고
    • Nerve growth factor-induced neurite sprouting in PC12 cells involves σ-1 receptors: Implications for antidepressants
    • Takebayashi M, Hayashi T, Su TP,. Nerve growth factor-induced neurite sprouting in PC12 cells involves σ-1 receptors: implications for antidepressants. J Pharmacol Exp Ther 2002; 303: 1227-1237.
    • (2002) J Pharmacol Exp Ther , vol.303 , pp. 1227-1237
    • Takebayashi, M.1    Hayashi, T.2    Su, T.P.3
  • 6
    • 3042759702 scopus 로고    scopus 로고
    • σ-1 receptors potentiate epidermal growth factor signaling towards neuritogenesis in PC12 cells: Potential relation to lipid raft reconstitution
    • Takebayashi M, Hayashi T, Su TP,. σ-1 receptors potentiate epidermal growth factor signaling towards neuritogenesis in PC12 cells: potential relation to lipid raft reconstitution. Synapse 2004; 53: 90-103.
    • (2004) Synapse , vol.53 , pp. 90-103
    • Takebayashi, M.1    Hayashi, T.2    Su, T.P.3
  • 7
    • 67349112448 scopus 로고    scopus 로고
    • Selective sigma receptor agonist 2-(4-morpholinethyl)1- phenylcyclohexanecarboxylate (PRE084) promotes neuroprotection and neurite elongation through protein kinase C (PKC) signaling on motoneurons
    • Guzmán-Lenis MS, Navarro X, Casas C,. Selective sigma receptor agonist 2-(4-morpholinethyl)1-phenylcyclohexanecarboxylate (PRE084) promotes neuroprotection and neurite elongation through protein kinase C (PKC) signaling on motoneurons. Neuroscience 2009; 162: 31-38.
    • (2009) Neuroscience , vol.162 , pp. 31-38
    • Guzmán-Lenis, M.S.1    Navarro, X.2    Casas, C.3
  • 14
    • 68949158949 scopus 로고    scopus 로고
    • Polymer-assisted solution-phase synthesis under combined ultrasound and microwave irradiation: Preparation of alpha,beta-unsaturated esters and carboxylic acids, key intermediates of novel sigma ligands
    • Rossi D, Urbano M, Carnevale Baraglia A, Serra M, Bergamelli F, Iannelli M, Azzolina O, Collina S,. Polymer-assisted solution-phase synthesis under combined ultrasound and microwave irradiation: preparation of alpha,beta-unsaturated esters and carboxylic acids, key intermediates of novel sigma ligands. Synth Comm 2009; 39: 3254-3262.
    • (2009) Synth Comm , vol.39 , pp. 3254-3262
    • Rossi, D.1    Urbano, M.2    Carnevale Baraglia, A.3    Serra, M.4    Bergamelli, F.5    Iannelli, M.6    Azzolina, O.7    Collina, S.8
  • 15
    • 36148930964 scopus 로고    scopus 로고
    • Microwave and polymer assisted synthesis of a small library of α,β-unsaturated methyl esters via the Wittig reaction
    • Collina S, Rossi D, Urbano M, Carnevale Baraglia A, Azzolina O,. Microwave and polymer assisted synthesis of a small library of α,β-unsaturated methyl esters via the Wittig reaction. Lett Org Chem 2007; 4: 384-387.
    • (2007) Lett Org Chem , vol.4 , pp. 384-387
    • Collina, S.1    Rossi, D.2    Urbano, M.3    Carnevale Baraglia, A.4    Azzolina, O.5
  • 16
    • 0037124758 scopus 로고    scopus 로고
    • Asymmetric hydrogenations
    • Knowles WS,. Asymmetric hydrogenations. Angew Chem Int Ed Engl 2002; 41: 1998-2007.
    • (2002) Angew Chem Int Ed Engl , vol.41 , pp. 1998-2007
    • Knowles, W.S.1
  • 18
    • 0000701744 scopus 로고    scopus 로고
    • Hydrogenation of funtionalized carbon-carbon double bonds
    • Jacobsen E.N. Pfaltz A. Yamamoto Y. editors. Chapter 5.1. Berlin: Springer.
    • Brown JM,. Hydrogenation of funtionalized carbon-carbon double bonds. In:, Jacobsen EN, Pfaltz A, Yamamoto Y, editors. Comprehensive asymmetric catalysis, Vol. I, Chapter 5.1. Berlin: Springer; 1999.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1
    • Brown, J.M.1
  • 19
    • 0037124885 scopus 로고    scopus 로고
    • Asymmetric catalysis: Science and opportunities
    • Noyori R,. Asymmetric catalysis: science and opportunities. Angew Chem Int Ed Engl 2002; 41: 2008-2022.
    • (2002) Angew Chem Int Ed Engl , vol.41 , pp. 2008-2022
    • Noyori, R.1
  • 20
    • 56549116899 scopus 로고    scopus 로고
    • Chiral HPLC for efficient resolution of enantiomers
    • Okamoto Y, Ikai T,. Chiral HPLC for efficient resolution of enantiomers. Chem Soc Rev 2008; 37 (12): 2593-2608.
    • (2008) Chem Soc Rev , vol.37 , Issue.12 , pp. 2593-2608
    • Okamoto, Y.1    Ikai, T.2
  • 21
    • 33646244248 scopus 로고    scopus 로고
    • Enantioselective chromatography and absolute configuration of N,N-dimethyl-3-(naphthalen-2-yl)-butan-1-amines: Potential sigma1 ligands
    • Collina S, Loddo G, Urbano M, Rossi D, Mamolo MG, Zampieri D, Alcaro S, Gallelli AA, Azzolina O,. Enantioselective chromatography and absolute configuration of N,N-dimethyl-3-(naphthalen-2-yl)-butan-1-amines: potential sigma1 ligands. Chirality 2006; 18: 245-253.
    • (2006) Chirality , vol.18 , pp. 245-253
    • Collina, S.1    Loddo, G.2    Urbano, M.3    Rossi, D.4    Mamolo, M.G.5    Zampieri, D.6    Alcaro, S.7    Gallelli, A.A.8    Azzolina, O.9
  • 22
    • 79960368560 scopus 로고    scopus 로고
    • Quick development of an analytical enantioselective high performance liquid chromatography separation and preparative scale-up for the flavonoid Naringenin
    • Gaggeri R, Rossi D, Collina S, Mannucci B, Baierl M, Juza M,. Quick development of an analytical enantioselective high performance liquid chromatography separation and preparative scale-up for the flavonoid Naringenin. J Chromatogr A 2011; 1218: 5414-5422.
    • (2011) J Chromatogr A , vol.1218 , pp. 5414-5422
    • Gaggeri, R.1    Rossi, D.2    Collina, S.3    Mannucci, B.4    Baierl, M.5    Juza, M.6
  • 23
    • 43249092579 scopus 로고    scopus 로고
    • The use of X-ray crystallography to determine absolute configuration
    • Flack HD, Bernardinelli G,. The use of X-ray crystallography to determine absolute configuration. Chirality 2008; 20: 681-690.
    • (2008) Chirality , vol.20 , pp. 681-690
    • Flack, H.D.1    Bernardinelli, G.2
  • 24
    • 74049088627 scopus 로고    scopus 로고
    • Enantiomer separation and indirect chromatographic absolute configuration prediction of chiral pirinixic acid derivatives: Limitations of polysaccharide-type chiral stationary phases in comparison to chiral anion-exchangers
    • Lämmerhofer M, Pell R, Mahut M, Richter M, Schiesel S, Zettl H, Dittrich M, Schubert-Zsilavecz M, Lindner W,. Enantiomer separation and indirect chromatographic absolute configuration prediction of chiral pirinixic acid derivatives: limitations of polysaccharide-type chiral stationary phases in comparison to chiral anion-exchangers. J Chromatogr A 2010; 1217: 1033-1040.
    • (2010) J Chromatogr A , vol.1217 , pp. 1033-1040
    • Lämmerhofer, M.1    Pell, R.2    Mahut, M.3    Richter, M.4    Schiesel, S.5    Zettl, H.6    Dittrich, M.7    Schubert-Zsilavecz, M.8    Lindner, W.9
  • 25
    • 60849101555 scopus 로고    scopus 로고
    • Absolute configurational assignment in chiral compounds through vibrational circular dichroism (VCD) spectroscopy
    • Uncuta C, Ion S, Gherase D, Bartha E, Teodorescu F, Filip P,. Absolute configurational assignment in chiral compounds through vibrational circular dichroism (VCD) spectroscopy. Rev Chim 2009; 60: 86-98.
    • (2009) Rev Chim , vol.60 , pp. 86-98
    • Uncuta, C.1    Ion, S.2    Gherase, D.3    Bartha, E.4    Teodorescu, F.5    Filip, P.6
  • 26
    • 79955453089 scopus 로고    scopus 로고
    • A vibrational circular dichroism approach to the determination of the absolute configurations of flavorous 5-substituted-2(5H)-furanones
    • Nakahashi A, Yaguchi Y, Miura N, Emura M, Monde K,. A vibrational circular dichroism approach to the determination of the absolute configurations of flavorous 5-substituted-2(5H)-furanones. J Nat Prod 2011; 74: 707-711.
    • (2011) J Nat Prod , vol.74 , pp. 707-711
    • Nakahashi, A.1    Yaguchi, Y.2    Miura, N.3    Emura, M.4    Monde, K.5
  • 28
    • 0002636574 scopus 로고    scopus 로고
    • Threonine-derived phosphinite-oxazoline ligands for the Ir-catalyzed enantioselective hydrogenation
    • Menges F, Pfaltz A,. Threonine-derived phosphinite-oxazoline ligands for the Ir-catalyzed enantioselective hydrogenation. Adv Synth Catal 2002; 344: 40-44.
    • (2002) Adv Synth Catal , vol.344 , pp. 40-44
    • Menges, F.1    Pfaltz, A.2
  • 29
    • 48149115998 scopus 로고    scopus 로고
    • Single-isomer trisubstituted olefins from a novel reaction of (E)-β-chloro-α-iodo-α,β-unsaturated esters and amides
    • Simard-Mercier J, Jiang JL, Ho ML, Flynn AB, Ogilvie WW,. Single-isomer trisubstituted olefins from a novel reaction of (E)-β-chloro-α-iodo- α,β-unsaturated esters and amides. J Org Chem 2008; 73: 5899-5906.
    • (2008) J Org Chem , vol.73 , pp. 5899-5906
    • Simard-Mercier, J.1    Jiang, J.L.2    Ho, M.L.3    Flynn, A.B.4    Ogilvie, W.W.5
  • 30
    • 33646261427 scopus 로고    scopus 로고
    • Single-isomer tetrasubstituted olefins from regioselective and stereospecific palladium-catalyzed coupling of β-chloro-α-iodo- α,β-unsaturated esters
    • Lemay AB, Vulic KS, Ogilvie WW,. Single-isomer tetrasubstituted olefins from regioselective and stereospecific palladium-catalyzed coupling of β-chloro-α-iodo-α,β-unsaturated esters. J Org Chem 2006; 71: 3615-3618.
    • (2006) J Org Chem , vol.71 , pp. 3615-3618
    • Lemay, A.B.1    Vulic, K.S.2    Ogilvie, W.W.3
  • 31
    • 0033552259 scopus 로고    scopus 로고
    • Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst
    • Appella DH, Moritani Y, Shintani R, Ferreira EM, Buchwald SL,. Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst. J Am Chem Soc 1999; 121: 9473-9474.
    • (1999) J Am Chem Soc , vol.121 , pp. 9473-9474
    • Appella, D.H.1    Moritani, Y.2    Shintani, R.3    Ferreira, E.M.4    Buchwald, S.L.5
  • 32
    • 75449101399 scopus 로고    scopus 로고
    • Semipreparative HPLC enantioseparation, chiroptical properties, and absolute configuration of two novel cyclooxygenase-2 inhibitors
    • Cirilli R, Fiore S, La Torre F, Maccioni E, Secci D, Sanna ML, Faggi C,. Semipreparative HPLC enantioseparation, chiroptical properties, and absolute configuration of two novel cyclooxygenase-2 inhibitors. Chirality 2010; 22: 56-62.
    • (2010) Chirality , vol.22 , pp. 56-62
    • Cirilli, R.1    Fiore, S.2    La Torre, F.3    Maccioni, E.4    Secci, D.5    Sanna, M.L.6    Faggi, C.7
  • 33
    • 84869878432 scopus 로고    scopus 로고
    • The sigma-1 receptor: Roles in neuronal plasticity and disease
    • Kourrich S, Su T-P, Fujimoto M, Bonci A,. The sigma-1 receptor:roles in neuronal plasticity and disease. Trends Neurosci 2012; 35: 762-771.
    • (2012) Trends Neurosci , vol.35 , pp. 762-771
    • Kourrich, S.1    Su, T.-P.2    Fujimoto, M.3    Bonci, A.4


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