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Volumn 12, Issue 9, 2003, Pages 481-511

Synthesis and evaluation of 5-substituted derivatives of 4,5-dihydro-3,3-diethyl-2(3H)-furanone as subtype-selective muscarinic leads

Author keywords

[No Author keywords available]

Indexed keywords

3,3 DIETHYL 4,5 DIHYDRO 5 [(2 ISOPROPYLIMIDAZOL 1 YL)ETHYL] 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 [(2 ISOPROPYLIMIDAZOL 1 YL)METHYL] 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 [(2 METHYLIMIDAZOL 1 YL)METHYL] 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 [(2 PROPYLIMIDAZOL 1 YL)METHYL] 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 [(IMIDAZOL 1 YL)ETHYL] 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 HYDROXYETHYL 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 IODOETHYL 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 MORPHOLINOETHYL 2(3H) FURANONE; 3,3 DIETHYL 4,5 DIHYDRO 5 PIPERIDINOETHYL 2(3H) FURANONE; 3,3 DIETHYL 5 IMIDAZOLYLMETHYL 2(3H) FURANONE; 5 [(2 ETHYLIMIDAZOL 1 YL)METHYL] 3,3 DIETHYL 4,5 DIHYDRO 2(3H) FURANONE; ALKYL GROUP; CHOLINERGIC RECEPTOR; FURANONE DERIVATIVE; IMIDAZOLE DERIVATIVE; MUSCARINIC AGENT; MUSCARINIC M1 RECEPTOR; MUSCARINIC M2 RECEPTOR; MUSCARINIC M3 RECEPTOR; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

EID: 3242878467     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (6)

References (48)
  • 1
    • 0032619996 scopus 로고    scopus 로고
    • Proceedings of the eighth international symposium on subtypes of muscarinic receptors
    • a) Levine, R. R. et al. Proceedings of the eighth international symposium on subtypes of muscarinic receptors. Life Sci. 1999, 64, 355-593.
    • (1999) Life Sci. , vol.64 , pp. 355-593
    • Levine, R.R.1
  • 2
    • 3242886823 scopus 로고    scopus 로고
    • Proceedings of the ninth international symposium on subtypes of muscarinic receptors
    • b) Levine, R. R. et al. Proceedings of the ninth international symposium on subtypes of muscarinic receptors. Life Sci. 2001, 65, 355-593.
    • (2001) Life Sci. , vol.65 , pp. 355-593
    • Levine, R.R.1
  • 3
    • 0031774720 scopus 로고    scopus 로고
    • International union of pharmacology. XVII. Classification of muscarinic acetylcholine receptors
    • c) Caulfield, M. P., Birdsall, N. J. M. International union of pharmacology. XVII. Classification of muscarinic acetylcholine receptors. Pharmacol. Rev. 1998, 50, 279-290.
    • (1998) Pharmacol. Rev. , vol.50 , pp. 279-290
    • Caulfield, M.P.1    Birdsall, N.J.M.2
  • 4
    • 0027398069 scopus 로고
    • The Diversity of neuronal nicotinic receptors
    • Sargent, P. The Diversity of neuronal nicotinic receptors. Annu. Rev. Neurosci. 1993, 16, 403-443.
    • (1993) Annu. Rev. Neurosci. , vol.16 , pp. 403-443
    • Sargent, P.1
  • 5
    • 0042661213 scopus 로고    scopus 로고
    • Novel insights into muscarinic acetylcholine receptor function using gene targeting technology
    • a) Wess, J. Novel insights into muscarinic acetylcholine receptor function using gene targeting technology. T.I.P.S. 2003, 24, 414-420.
    • (2003) T.I.P.S. , vol.24 , pp. 414-420
    • Wess, J.1
  • 6
    • 0034676312 scopus 로고    scopus 로고
    • Therapeutic opportunities for muscarinic receptors in the central nervous system
    • b) Felder, C. C. et al. Therapeutic opportunities for muscarinic receptors in the central nervous system. J. Med. Chem. 2000, 43, 4333-4353.
    • (2000) J. Med. Chem. , vol.43 , pp. 4333-4353
    • Felder, C.C.1
  • 7
    • 0033179509 scopus 로고    scopus 로고
    • Muscarinic receptor ligands and their therapeutic potential
    • c) Eglen, R.M., et al. Muscarinic receptor ligands and their therapeutic potential. Curr. Opin. Chem. Biol. 1999, 3, 426-432.
    • (1999) Curr. Opin. Chem. Biol. , vol.3 , pp. 426-432
    • Eglen, R.M.1
  • 8
    • 0002793827 scopus 로고    scopus 로고
    • Targeting nicotinic acetylcholine receptors: Advances in molecular design and therapies
    • Robertson, Ed., Academic press, Inc, and references cited therein
    • a) Schmitt, J.D.; Bencherif, M. Targeting nicotinic acetylcholine receptors: Advances in molecular design and therapies. In Annual Reports in Med. Chem., Vol 35, Robertson, Ed., Academic press, Inc, 2000, pp 41-51 (and references cited therein).
    • (2000) Annual Reports in Med. Chem. , vol.35 , pp. 41-51
    • Schmitt, J.D.1    Bencherif, M.2
  • 9
    • 0033960085 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors as novel drug targets
    • b) Lloyd, G. K.; Williams, M. Neuronal nicotinic acetylcholine receptors as novel drug targets. J.P.E.T. 2000, 292, 461-467.
    • (2000) J.P.E.T. , vol.292 , pp. 461-467
    • Lloyd, G.K.1    Williams, M.2
  • 10
    • 0034213308 scopus 로고    scopus 로고
    • Novel potent ligands for the central nicotinic acetylcholine receptor: Synthesis, receptor binding, and 3D-QSAR analysis
    • c) Nielsen, S. F.; Nielsen, E. O.; Olsen, G. M.; Liljefors, T.; Peters, D. Novel potent ligands for the central nicotinic acetylcholine receptor: Synthesis, receptor binding, and 3D-QSAR analysis. J. Med. Chem. 2000, 43, 2217-2226.
    • (2000) J. Med. Chem. , vol.43 , pp. 2217-2226
    • Nielsen, S.F.1    Nielsen, E.O.2    Olsen, G.M.3    Liljefors, T.4    Peters, D.5
  • 11
    • 0034732104 scopus 로고    scopus 로고
    • Allosteric modulation of nicotinic acetylcholine receptors as a treatment strategy for Alzheimer's Disease
    • d) Maelicke, A.; Albuquerque, E. X. Allosteric modulation of nicotinic acetylcholine receptors as a treatment strategy for Alzheimer's Disease. Europ. J. Pharmacol. 2000, 393, 165-170.
    • (2000) Europ. J. Pharmacol. , vol.393 , pp. 165-170
    • Maelicke, A.1    Albuquerque, E.X.2
  • 12
    • 0034732362 scopus 로고    scopus 로고
    • The identification of novel structural compound classes exhibiting high affinity for neuronal nicotine acetylcholine receptors and analgesic efficacy in preclinical models of pain
    • e) Meyer, M. D.; Decker, M. W.; Rueter, L. E.; Anderson, D. J.; Dart, M. J.; Kim, K. H.; Sullivan, J. P.; Williams, M. The identification of novel structural compound classes exhibiting high affinity for neuronal nicotine acetylcholine receptors and analgesic efficacy in preclinical models of pain. Europ. J. Pharmacol. 2000, 393, 171-177.
    • (2000) Europ. J. Pharmacol. , vol.393 , pp. 171-177
    • Meyer, M.D.1    Decker, M.W.2    Rueter, L.E.3    Anderson, D.J.4    Dart, M.J.5    Kim, K.H.6    Sullivan, J.P.7    Williams, M.8
  • 13
    • 0031450275 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors as targets for drug discovery
    • f) Holladay, M.W.; Dart, M.J.; Lynch, J.K. Neuronal nicotinic acetylcholine receptors as targets for drug discovery. J. Med. Chem. 1997, 40, 4169-4194.
    • (1997) J. Med. Chem. , vol.40 , pp. 4169-4194
    • Holladay, M.W.1    Dart, M.J.2    Lynch, J.K.3
  • 15
    • 0023134666 scopus 로고
    • Molecular modification of anticholinergics as probes for muscarinic receptors. 3. Conformationally restricted analogues of benactyzine
    • b) Flavin, M.T.; Lu, M.C.; Thompson, E.B.; Bhargava, H.N. Molecular modification of anticholinergics as probes for muscarinic receptors. 3. Conformationally restricted analogues of benactyzine. J. Med. Chem. 1987, 30, 278-285.
    • (1987) J. Med. Chem. , vol.30 , pp. 278-285
    • Flavin, M.T.1    Lu, M.C.2    Thompson, E.B.3    Bhargava, H.N.4
  • 16
    • 0014934202 scopus 로고
    • Structure and activity of acetylcholine
    • Beers, W. H.; Reich, E. Structure and activity of acetylcholine. Nature 1970, 228, 917-922.
    • (1970) Nature , vol.228 , pp. 917-922
    • Beers, W.H.1    Reich, E.2
  • 17
    • 0022485091 scopus 로고
    • The Ensemble approach to distance geometry: Application to the nicotinic pharmacophore
    • Sheridan, R.P.; Nilakantan, R.; Dixon, J.S.; Venkataraghavan, R. The Ensemble approach to distance geometry: Application to the nicotinic pharmacophore. J. Med. Chem. 1986, 29, 899-906.
    • (1986) J. Med. Chem. , vol.29 , pp. 899-906
    • Sheridan, R.P.1    Nilakantan, R.2    Dixon, J.S.3    Venkataraghavan, R.4
  • 18
    • 0000949429 scopus 로고
    • Epibatidine-Aided studies toward definition of a nicotine receptor pharmacophore
    • a) Glennon, R. A.; Herndon J. L.; Dukat, M. Epibatidine-Aided studies toward definition of a nicotine receptor pharmacophore. Med. Chem. Res., 1994, 4, 461-473.
    • (1994) Med. Chem. Res. , vol.4 , pp. 461-473
    • Glennon, R.A.1    Herndon, J.L.2    Dukat, M.3
  • 20
    • 0032719341 scopus 로고    scopus 로고
    • Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d]azepine and related ring-opened analogs at central nicotinic receptors
    • c) Cheng, Y.-X.; Dukat, M.; Dowd, M.; Fiedler, W.; Martin, B.; Damaj, M. I.; Glennon, R.A. Synthesis and binding of 6,7,8,9-tetrahydro-5H-pyrido[3,4-d] azepine and related ring-opened analogs at central nicotinic receptors. Eur. J. Med. Chem. 1999, 34, 177.
    • (1999) Eur. J. Med. Chem. , vol.34 , pp. 177
    • Cheng, Y.-X.1    Dukat, M.2    Dowd, M.3    Fiedler, W.4    Martin, B.5    Damaj, M.I.6    Glennon, R.A.7
  • 21
    • 0034078072 scopus 로고    scopus 로고
    • Central nicotinic receptor ligands and pharmacophores
    • d) Glennon, R.A.; Dukat, M. Central nicotinic receptor ligands and pharmacophores. Pharm. Acta Helv. 2000, 74, 103-114.
    • (2000) Pharm. Acta Helv. , vol.74 , pp. 103-114
    • Glennon, R.A.1    Dukat, M.2
  • 22
    • 0033549847 scopus 로고    scopus 로고
    • Molecular recognition in nicotinic receptor: The importance of π-cation interaction
    • Schmitt, J.D.; Sharpless, C. G. V.; Caldwell, W.S. Molecular recognition in nicotinic receptor: The importance of π-cation interaction. J. Med. Chem. 1999, 42, 3066-3074.
    • (1999) J. Med. Chem. , vol.42 , pp. 3066-3074
    • Schmitt, J.D.1    Sharpless, C.G.V.2    Caldwell, W.S.3
  • 23
    • 0033518276 scopus 로고    scopus 로고
    • Improving the nicotinic pharmacophore with a series of (isoxazole)methylene-1-azacyclic compounds: Synthesis, structure-activity relationship, and molecular modeling
    • a) Tonder, J.E.; Hansen J. B.; Begtrup, M.; Pettersson, I.; Rimvall, K.; Christensen, B.; Ehrbar, U.; Olesen, P. H. Improving the nicotinic pharmacophore with a series of (isoxazole)methylene-1-azacyclic compounds: Synthesis, structure-activity relationship, and molecular modeling. J. Med. Chem. 1999, 42, 4970-4980.
    • (1999) J. Med. Chem. , vol.42 , pp. 4970-4980
    • Tonder, J.E.1    Hansen, J.B.2    Begtrup, M.3    Pettersson, I.4    Rimvall, K.5    Christensen, B.6    Ehrbar, U.7    Olesen, P.H.8
  • 26
    • 0026575010 scopus 로고
    • Muscarinic activity of the thiolactone, lactam, lactol, and thiolactol analogues of pilocarpine and a hypothetical model for the binding of agonists to the ml receptor
    • a) Shapiro, G.; Floersheim, P.; Boelsterilli, J.; Amstutz, R.; Bolliger, G.; Gammenthaler, H.; Gmelin, G.; Supavilai, P.; Walkinshaw, M. Muscarinic activity of the thiolactone, lactam, lactol, and thiolactol analogues of pilocarpine and a hypothetical model for the binding of agonists to the ml receptor. J. Med. Chem. 1992, 35, 15-27.
    • (1992) J. Med. Chem. , vol.35 , pp. 15-27
    • Shapiro, G.1    Floersheim, P.2    Boelsterilli, J.3    Amstutz, R.4    Bolliger, G.5    Gammenthaler, H.6    Gmelin, G.7    Supavilai, P.8    Walkinshaw, M.9
  • 27
    • 0027278101 scopus 로고
    • Binding-Site modeling of the muscarinic ml receptor: A combination or homology-based and indirect approaches
    • b) Nordvall, G.; Hacksell, U. Binding-Site modeling of the muscarinic ml receptor: A combination or homology-based and indirect approaches. J. Med. Chem. 1993, 36, 967-976.
    • (1993) J. Med. Chem. , vol.36 , pp. 967-976
    • Nordvall, G.1    Hacksell, U.2
  • 29
    • 1842421969 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of aminomethyl/amidomethyl derivatives of an anticonvulsant gamma-butyrolactone
    • a) Ahungena, A.; Canney, D.J. Synthesis and biological evaluation of aminomethyl/amidomethyl derivatives of an anticonvulsant gamma-butyrolactone. Med. Chem. Res. 1996, 6:9, 618-634.
    • (1996) Med. Chem. Res. , vol.6 , Issue.9 , pp. 618-634
    • Ahungena, A.1    Canney, D.J.2
  • 30
    • 0001631004 scopus 로고
    • Electrophilic lactonization as a tool in acyclic stereocontrol. Synthesis of Serricomin
    • b) Bartlett, P. A.; Richardson, D. P.; Myerson, J. Electrophilic lactonization as a tool in acyclic stereocontrol. Synthesis of Serricomin. Tetrahedron 1984, 40, 2317-2327.
    • (1984) Tetrahedron , vol.40 , pp. 2317-2327
    • Bartlett, P.A.1    Richardson, D.P.2    Myerson, J.3
  • 31
    • 0021097053 scopus 로고
    • Iodolactonization of allylic alcohol derivatives containing internal nucleophiles. Control of stereoselectivity by substituents in acyclic precursors
    • c) Chamberlin, A.R.; Dezube, M.; Dussault, P.; McMills, M.C. Iodolactonization of allylic alcohol derivatives containing internal nucleophiles. Control of stereoselectivity by substituents in acyclic precursors. J. Am. Chem. Soc. 1983, 105, 5819-5825.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 5819-5825
    • Chamberlin, A.R.1    Dezube, M.2    Dussault, P.3    McMills, M.C.4
  • 32
    • 33947488081 scopus 로고
    • Mechanism of the Prins Reaction. Stereoaspects of the formation of 1,3-Dioxanes
    • Smissman, E.E.; Schnettler, R.A.; Portoghese, P.S. Mechanism of the Prins Reaction. Stereoaspects of the formation of 1,3-Dioxanes. J. Org. Chem. 1965, 30, 797-801.
    • (1965) J. Org. Chem. , vol.30 , pp. 797-801
    • Smissman, E.E.1    Schnettler, R.A.2    Portoghese, P.S.3
  • 33
    • 0013494728 scopus 로고
    • Demethylation of aryl methyl ethers by boron tribromide
    • McOmie, J. F. W.; Watts, M. L.; West, D. E. Demethylation of aryl methyl ethers by boron tribromide. Tetrahedron 1968, 24, 2289-2292.
    • (1968) Tetrahedron , vol.24 , pp. 2289-2292
    • McOmie, J.F.W.1    Watts, M.L.2    West, D.E.3
  • 34
    • 0032578897 scopus 로고    scopus 로고
    • Efficient preparation of E-β-iodovinyl phenylsulfone by Finkelstein reaction at a vinyl center
    • Zoller, T.; Uguen, D.; DeClan, A.; Fischer, J. Efficient preparation of E-β-iodovinyl phenylsulfone by Finkelstein reaction at a vinyl center. Tetrahedron Letters 1998, 39, 8089-8092.
    • (1998) Tetrahedron Letters , vol.39 , pp. 8089-8092
    • Zoller, T.1    Uguen, D.2    DeClan, A.3    Fischer, J.4
  • 35
    • 0027266977 scopus 로고
    • Proposed atomic structure of a truncated human immunodeficiency virus glycoprotein gp120 derived by molecular modeling: Target CD4 recognition and docking mechanism
    • Gabriel, J.L.; Mitchell, W.M. Proposed atomic structure of a truncated human immunodeficiency virus glycoprotein gp120 derived by molecular modeling: Target CD4 recognition and docking mechanism. Proc. Natl. Acad. Sci. USA 1993, 90, 4186-4191.
    • (1993) Proc. Natl. Acad. Sci. USA , vol.90 , pp. 4186-4191
    • Gabriel, J.L.1    Mitchell, W.M.2
  • 36
    • 3242889085 scopus 로고    scopus 로고
    • HIV GP120 docking interactions and inhibitor design based on an atomic structure derived by molecular modeling using the DREIDING II force field
    • Bohr, H.; Brunak, S., Eds.
    • Gabriel, J. L.; Mitchell, W. M. HIV GP120 docking interactions and inhibitor design based on an atomic structure derived by molecular modeling using the DREIDING II force field. In protein folds: A distance-based approach, Bohr, H.; Brunak, S., Eds.; 1996, 294-307.
    • (1996) Protein Folds: A Distance-based Approach , pp. 294-307
    • Gabriel, J.L.1    Mitchell, W.M.2
  • 37
    • 0001178537 scopus 로고    scopus 로고
    • Synthesis and preliminary biological evaluation of 3-substited quinuclidines as nicotinic ligands
    • Canney, D., J., et.al., Synthesis and preliminary biological evaluation of 3-substited quinuclidines as nicotinic ligands. Med Chem Res. 1997, 7:5, 282-300.
    • (1997) Med Chem Res. , vol.7 , Issue.5 , pp. 282-300
    • Canney, D.J.1
  • 39
    • 3242891312 scopus 로고
    • 3H]Pirenzepine and [3H]QNB binding to brain muscarinic cholinergic receptors
    • 3H]Pirenzepine and [3H]QNB binding to brain muscarinic cholinergic receptors. Mol. Pharmacol. 1984, 26, 161-169.
    • (1984) Mol. Pharmacol. , vol.26 , pp. 161-169
    • Luthin, G.R.1    Wolfe, B.B.2
  • 40
    • 0022469652 scopus 로고
    • Binding profile of a novel cardioselective muscarine receptor antagonist, AF-DX 116, to membranes of peripheral tissues and brain in the rat
    • Hammer, R., Giraldo, E. et al. Binding profile of a novel cardioselective muscarine receptor antagonist, AF-DX 116, to membranes of peripheral tissues and brain in the rat. Life Sciences 1986, 38, 1653-1662.
    • (1986) Life Sciences , vol.38 , pp. 1653-1662
    • Hammer, R.1    Giraldo, E.2
  • 43
    • 0025328968 scopus 로고
    • 3 Muscarinic cholinergic receptors: Binding characteristics of agonists and antagonists
    • 3 Muscarinic cholinergic receptors: binding characteristics of agonists and antagonists. J. Neurolog. Sci. 1990, 97, 67-80.
    • (1990) J. Neurolog. Sci. , vol.97 , pp. 67-80
    • Vanderheyden, P.1    Gies, J.-P.2
  • 45
    • 0025924689 scopus 로고
    • [3H] Cytisine binding to nicotinic cholinergic receptors in brain
    • Pabreza, L. A.; Dhawan, S.; Kellar. K. J. [3H] Cytisine binding to nicotinic cholinergic receptors in brain. Molec Pharmacol. 1990, 39, 9-12.
    • (1990) Molec Pharmacol. , vol.39 , pp. 9-12
    • Pabreza, L.A.1    Dhawan, S.2    Kellar, K.J.3
  • 46
    • 0023143354 scopus 로고
    • Pilocarpine-induced reciprocal hindlimb scratching in mice
    • Scott, R. W.; Goode, T. L.; Raffa, R.B. Pilocarpine-induced reciprocal hindlimb scratching in mice. Pharmacol. Biochem. Behav. 1987, 26, 327-331.
    • (1987) Pharmacol. Biochem. Behav. , vol.26 , pp. 327-331
    • Scott, R.W.1    Goode, T.L.2    Raffa, R.B.3
  • 48
    • 0024234784 scopus 로고
    • Reciprocal hindlimb scratching and putative subtype-selective muscarinic agents
    • Raffa, R.B.; Ortegon, M.E.; Watson, M. Reciprocal hindlimb scratching and putative subtype-selective muscarinic agents. Eur. J. Pharmacol. 1988, 158, 289-292.
    • (1988) Eur. J. Pharmacol. , vol.158 , pp. 289-292
    • Raffa, R.B.1    Ortegon, M.E.2    Watson, M.3


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