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Volumn 49, Issue 12, 2006, Pages 3628-3635

Fancy bioisosteres: Novel paracyclophane derivatives as super-affinity dopamine D3 receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; DOPAMINE 3 RECEPTOR BLOCKING AGENT; GPCR LIGAND; GUANINE NUCLEOTIDE BINDING PROTEIN; LIGAND; N [4 [4 (2 METHOXYPHENYL)PIPERAZIN 1 YL]BUTYL[2,2]PARACYCLOPHANE 4 CARBOXAMIDE; PARACYCLOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33745182275     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060138d     Document Type: Article
Times cited : (29)

References (37)
  • 1
    • 36148959779 scopus 로고    scopus 로고
    • The use of bioisosteric groups in lead optimization
    • Chen, X.; Wang, W. The use of bioisosteric groups in lead optimization. Annu. Rep. Med. Chem. 2003, 38, 333-346.
    • (2003) Annu. Rep. Med. Chem. , vol.38 , pp. 333-346
    • Chen, X.1    Wang, W.2
  • 2
    • 0038248584 scopus 로고    scopus 로고
    • Conjugated enynes as nonaromatic catechol bioisosteres: Synthesis, binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D3 subtype
    • (a) Hübner, H.; Haubmann, C.; Utz, W.; Gmeiner, P. Conjugated enynes as nonaromatic catechol bioisosteres: synthesis, binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D3 subtype. J. Med. Chem. 2000, 43, 756-762.
    • (2000) J. Med. Chem. , vol.43 , pp. 756-762
    • Hübner, H.1    Haubmann, C.2    Utz, W.3    Gmeiner, P.4
  • 3
    • 9644276854 scopus 로고    scopus 로고
    • Fancy bioisosteres: Synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel nonaromatic D3 agonist
    • (b) Lenz, C.; Haubmann, C.; Huebner, H.; Boeckler, F.; Gmeiner, P. Fancy bioisosteres: synthesis and dopaminergic properties of the endiyne FAUC 88 as a novel nonaromatic D3 agonist. Bioorg. Med. Chem. 2005, 13, 185-191.
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 185-191
    • Lenz, C.1    Haubmann, C.2    Huebner, H.3    Boeckler, F.4    Gmeiner, P.5
  • 4
    • 0035794960 scopus 로고    scopus 로고
    • Indoloparacyclophanes: Synthesis and dopamine receptor binding of a novel arylbioisostere
    • (a) Ortner, B.; Waibel, R.; Gmeiner, P. Indoloparacyclophanes: synthesis and dopamine receptor binding of a novel arylbioisostere. Angew. Chem., Int. Ed. 2001, 40. 1283-1285.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1283-1285
    • Ortner, B.1    Waibel, R.2    Gmeiner, P.3
  • 5
    • 0035842876 scopus 로고    scopus 로고
    • Planar chiral indoles: Synthesis and biological effects of the enantiomers
    • (b) Ortner, B.; Hübner, H.; Gmeiner, P. Planar chiral indoles: synthesis and biological effects of the enantiomers. Tetrahedron: Asymmetry 2001, 12, 3205-3208.
    • (2001) Tetrahedron: Asymmetry , vol.12 , pp. 3205-3208
    • Ortner, B.1    Hübner, H.2    Gmeiner, P.3
  • 6
    • 0037057547 scopus 로고    scopus 로고
    • Interactive SAR studies: Rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists
    • (a) Bettinetti, L.; Schlotter, K.; Hübner, H.; Gmeiner, P. Interactive SAR studies: rational discovery of super-potent and highly selective dopamine D3 receptor antagonists and partial agonists. J. Med. Chem. 2002, 45, 4594-4597.
    • (2002) J. Med. Chem. , vol.45 , pp. 4594-4597
    • Bettinetti, L.1    Schlotter, K.2    Hübner, H.3    Gmeiner, P.4
  • 7
    • 0043264004 scopus 로고    scopus 로고
    • Attenuation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxicity by the novel selective dopamine D3-receptor partial agonist FAUC 329 predominantly in the nucleus accumbens of mice
    • (b) Boeckler, F.; Leng, A.; Mura, A. Bettinetti, L.; Feldon, J.; Gmeiner, P.; Ferger, B. Attenuation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxicity by the novel selective dopamine D3-receptor partial agonist FAUC 329 predominantly in the nucleus accumbens of mice. Biochem. Pharmacol. 2003, 66, 1025-1032.
    • (2003) Biochem. Pharmacol. , vol.66 , pp. 1025-1032
    • Boeckler, F.1    Leng, A.2    Mura, A.3    Bettinetti, L.4    Feldon, J.5    Gmeiner, P.6    Ferger, B.7
  • 8
    • 20144375764 scopus 로고    scopus 로고
    • Fancy bioisosteres: Metallocene-derived G-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles
    • Schlotter, K.; Boeckler, F.; Hübner, H.; Gmeiner, P. Fancy bioisosteres: metallocene-derived G-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles. J. Med. Chem. 2005, 48, 3696-3699.
    • (2005) J. Med. Chem. , vol.48 , pp. 3696-3699
    • Schlotter, K.1    Boeckler, F.2    Hübner, H.3    Gmeiner, P.4
  • 11
    • 0037137596 scopus 로고    scopus 로고
    • Structure-affinity relationship study on N-[4-(4-arylpiperazin-1-yl) butyl]arylcarboxamides as potent and selective dopamine D3 receptor ligands
    • Leopoldo, M.; Berardi, F.; Colabufo, N. A.; De Giorgio, P.; Lacivita, E.; Perrone, R.; Tortorella, V. Structure-affinity relationship study on N-[4-(4-arylpiperazin-1-yl)butyl]arylcarboxamides as potent and selective dopamine D3 receptor ligands. J. Med. Chem. 2002, 45, 5727-5735.
    • (2002) J. Med. Chem. , vol.45 , pp. 5727-5735
    • Leopoldo, M.1    Berardi, F.2    Colabufo, N.A.3    De Giorgio, P.4    Lacivita, E.5    Perrone, R.6    Tortorella, V.7
  • 12
    • 0034712156 scopus 로고    scopus 로고
    • Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates
    • (a) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. J. Org. Chem. 2000, 65, 1158-1174.
    • (2000) J. Org. Chem. , vol.65 , pp. 1158-1174
    • Wolfe, J.P.1    Tomori, H.2    Sadighi, J.P.3    Yin, J.4    Buchwald, S.L.5
  • 13
    • 0032541260 scopus 로고    scopus 로고
    • Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and Inflates: Scope and mechanism
    • (b) Hartwig, J. F. Transition metal catalyzed synthesis of arylamines and aryl ethers from aryl halides and Inflates: scope and mechanism. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2046-2067
    • Hartwig, J.F.1
  • 14
    • 0032510005 scopus 로고    scopus 로고
    • Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst
    • (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst. Tetrahedron Lett. 1998, 39, 617-620.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 617-620
    • Nishiyama, M.1    Yamamoto, T.2    Koie, Y.3
  • 15
    • 0036973460 scopus 로고    scopus 로고
    • Progress in arylpiperazine synthesis by the catalytic amination reaction
    • (b) Torisawa, Y.; Nishi, T.; Minamikawa, J.-i. Progress in arylpiperazine synthesis by the catalytic amination reaction. Bioorg. Med. Chem. 2002, 10, 4023-4027.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 4023-4027
    • Torisawa, Y.1    Nishi, T.2    Minamikawa, J.-I.3
  • 17
    • 0038579160 scopus 로고    scopus 로고
    • Attenuation of levodopa-induced dyskinesia by normalizing dopamine D3 receptor function
    • (b) Bezard, E.; Ferry, S.; Mach, U.; Stark, H.; Leriche, L.; Boraud, T.; Gross, C.; Sokoloff, P. Attenuation of levodopa-induced dyskinesia by normalizing dopamine D3 receptor function. Nat. Med. 2003, 9, 762-767.
    • (2003) Nat. Med. , vol.9 , pp. 762-767
    • Bezard, E.1    Ferry, S.2    Mach, U.3    Stark, H.4    Leriche, L.5    Boraud, T.6    Gross, C.7    Sokoloff, P.8
  • 18
    • 0026695537 scopus 로고
    • Structural subtypes of the dopamine D2 receptor are functionally distinct: Expression of the cloned D2A and D2B subtypes in a heterologous cell line
    • Hayes, G.; Biden, T. J.; Selbie, L. A.; Shine, J. Structural subtypes of the dopamine D2 receptor are functionally distinct: expression of the cloned D2A and D2B subtypes in a heterologous cell line. Mol. Endocrinol. 1992, 6, 920-926.
    • (1992) Mol. Endocrinol. , vol.6 , pp. 920-926
    • Hayes, G.1    Biden, T.J.2    Selbie, L.A.3    Shine, J.4
  • 20
    • 0029120447 scopus 로고
    • Modulation of intracellular cyclic AMP levels by different human dopamine D4 receptor variants
    • Asghari, V.; Sanyal, S.; Buchwaldt, S.; Paterson, A.; Jovanovic, V.; Van Tol, H. H. M. Modulation of intracellular cyclic AMP levels by different human dopamine D4 receptor variants. J. Neurochem. 1995, 65, 1157-1165.
    • (1995) J. Neurochem. , vol.65 , pp. 1157-1165
    • Asghari, V.1    Sanyal, S.2    Buchwaldt, S.3    Paterson, A.4    Jovanovic, V.5    Van Tol, H.H.M.6
  • 22
    • 0034676321 scopus 로고    scopus 로고
    • Cyanoindole derivatives as highly selective dopamine D4 receptor partial agonists: Solid-phase synthesis, binding assays, and functional experiments
    • (b) Hübner, H.; Kraxner, J.; Gmeiner, P. Cyanoindole derivatives as highly selective dopamine D4 receptor partial agonists: solid-phase synthesis, binding assays, and functional experiments. J. Med. Chem. 2000, 43, 4563-4569.
    • (2000) J. Med. Chem. , vol.43 , pp. 4563-4569
    • Hübner, H.1    Kraxner, J.2    Gmeiner, P.3
  • 23
    • 0028012102 scopus 로고
    • Activation of heterologously expressed D3 dopamine receptors: Comparison with D2 dopamine receptors
    • Chio, C.; Lajiness, M. E.; Huff, R. M. Activation of heterologously expressed D3 dopamine receptors: comparison with D2 dopamine receptors. Mol. Pharmacol. 1994, 45, 51-60.
    • (1994) Mol. Pharmacol. , vol.45 , pp. 51-60
    • Chio, C.1    Lajiness, M.E.2    Huff, R.M.3
  • 26
    • 0346671325 scopus 로고    scopus 로고
    • Analogues of FAUC 73 revealing new insights into the structural requirements of nonaromatic dopamine D3 receptor agonists
    • Lenz, C.; Boeckler, F.; Hubner, H.; Gmeiner, P. Analogues of FAUC 73 revealing new insights into the structural requirements of nonaromatic dopamine D3 receptor agonists. Bioorg. Med. Chem. 2004, 12, 113-117.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 113-117
    • Lenz, C.1    Boeckler, F.2    Hubner, H.3    Gmeiner, P.4
  • 27
    • 20444468075 scopus 로고    scopus 로고
    • Fancy bioisosteres: Synthesis, SAR, and pharmacological investigations of novel non-aromatic dopamine D3 receptor ligands
    • Lenz, C.; Boeckler, F.; Hübner, H.; Gmeiner, P. Fancy bioisosteres: synthesis, SAR, and pharmacological investigations of novel non-aromatic dopamine D3 receptor ligands. Bioorg. Med. Chem. 2005, 13, 4434-4442.
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 4434-4442
    • Lenz, C.1    Boeckler, F.2    Hübner, H.3    Gmeiner, P.4
  • 28
    • 11744305193 scopus 로고
    • Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations
    • Wolinski, K.; Hinton, J. F.; Pulay, P. Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 1990, 112, 8251-8260.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8251-8260
    • Wolinski, K.1    Hinton, J.F.2    Pulay, P.3
  • 29
    • 0242417008 scopus 로고    scopus 로고
    • Interactions with Aromatic Rings in Chemical and Biological Recognition
    • Meyer, E. A.; Castellano, R. K.; Diederich, F. Interactions with Aromatic Rings in Chemical and Biological Recognition. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 1210-1250
    • Meyer, E.A.1    Castellano, R.K.2    Diederich, F.3
  • 30
    • 0001752768 scopus 로고    scopus 로고
    • The Cambridge Structural Database: A quarter of a million crystal structures and rising
    • Allen, F. H. The Cambridge Structural Database: a quarter of a million crystal structures and rising. Acta Crystallogr., Sect. B 2002, 58, 380-388.
    • (2002) Acta Crystallogr., Sect. B , vol.58 , pp. 380-388
    • Allen, F.H.1
  • 31
    • 0003547702 scopus 로고    scopus 로고
    • Wave Function, Inc.: Irvine, CA
    • PC Spartan Plus, version 1.5; Wave Function, Inc.: Irvine, CA, 1998.
    • (1998) PC Spartan Plus, Version 1.5
  • 32
    • 33745169096 scopus 로고    scopus 로고
    • Tripos Inc.: St. Louis, MO
    • SYBYL6.9: Tripos Inc.: St. Louis, MO, 2003.
    • (2003) SYBYL6.9
  • 33
    • 0000700630 scopus 로고
    • Macro Rings. XII. Stereochemical consequences of steric compression in the smallest paracyclophane
    • Cram, D. J.; Allinger, N. L. Macro Rings. XII. Stereochemical consequences of steric compression in the smallest paracyclophane. J. Am. Chem. Soc. 1955, 77, 6289-6294.
    • (1955) J. Am. Chem. Soc. , vol.77 , pp. 6289-6294
    • Cram, D.J.1    Allinger, N.L.2
  • 34
    • 33947337088 scopus 로고
    • Macro Rings. XXXI. Quinone derived from [2.2]paracyclophane, an intramolecular-molecular complex
    • Cram, D. J.; Day, A. C. Macro Rings. XXXI. Quinone derived from [2.2]paracyclophane, an intramolecular-molecular complex. J. Org. Chem. 1966, 31, 1227-1232.
    • (1966) J. Org. Chem. , vol.31 , pp. 1227-1232
    • Cram, D.J.1    Day, A.C.2
  • 35
    • 0000018043 scopus 로고
    • Absolute configuration and circular dichroism of optically active [2.2]paracyclophane derivatives
    • Falk, H.; Reich-Rohrwig, P.; Schlogl, K. Absolute configuration and circular dichroism of optically active [2.2]paracyclophane derivatives. Tetrahedron 1970, 26, 511-527.
    • (1970) Tetrahedron , vol.26 , pp. 511-527
    • Falk, H.1    Reich-Rohrwig, P.2    Schlogl, K.3


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