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Volumn 5, Issue 5, 2014, Pages 550-555

Design, synthesis, and optimization of balanced dual NK1/NK 3 receptor antagonists

Author keywords

molecular hybridization; peptidomimetic; Schizophrenia

Indexed keywords

NEUROKININ 1 RECEPTOR ANTAGONIST; NEUROKININ 3 RECEPTOR ANTAGONIST;

EID: 84900461848     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400528y     Document Type: Article
Times cited : (15)

References (60)
  • 2
    • 4544243318 scopus 로고    scopus 로고
    • The NK(1) receptor antagonist WIN51708 reduces sensitization after chronic cocaine
    • Davidson, C.; Lee, T. H.; Ellinwood, E. H. The NK(1) receptor antagonist WIN51708 reduces sensitization after chronic cocaine Eur. J. Pharmacol. 2004, 499, 55
    • (2004) Eur. J. Pharmacol. , vol.499 , pp. 55
    • Davidson, C.1    Lee, T.H.2    Ellinwood, E.H.3
  • 3
    • 33644671816 scopus 로고    scopus 로고
    • Opinion: NK3 receptor antagonists: The next generation of antipsychotics?
    • Spooren, W.; Riemer, C.; Meltzer, H. Opinion: NK3 receptor antagonists: the next generation of antipsychotics? Nat. Rev. Drug Discovery 2005, 4, 967
    • (2005) Nat. Rev. Drug Discovery , vol.4 , pp. 967
    • Spooren, W.1    Riemer, C.2    Meltzer, H.3
  • 4
    • 77949429901 scopus 로고    scopus 로고
    • Therapeutic utility of NK3 receptor antagonists for the treatment of schizophrenia
    • Dawson, L. A.; Smith, P. W. Therapeutic utility of NK3 receptor antagonists for the treatment of schizophrenia Curr. Pharm. Des. 2010, 16, 344
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 344
    • Dawson, L.A.1    Smith, P.W.2
  • 7
    • 84863085673 scopus 로고    scopus 로고
    • Multi-target drugs: The trend of drug research and development
    • Lu, J.-J.; Pan, W.; Hu, Y.-J.; Wang, Y.-T. Multi-target drugs: the trend of drug research and development PLoS One 2012, 7, e40262
    • (2012) PLoS One , vol.7 , pp. 40262
    • Lu, J.-J.1    Pan, W.2    Hu, Y.-J.3    Wang, Y.-T.4
  • 8
    • 57749090403 scopus 로고    scopus 로고
    • Dual- and triple-acting agents for treating core and co-morbid symptoms of major depression: Novel concepts, new drugs
    • Millan, M. J. Dual- and triple-acting agents for treating core and co-morbid symptoms of major depression: novel concepts, new drugs Neurotherapeutics 2009, 6, 53
    • (2009) Neurotherapeutics , vol.6 , pp. 53
    • Millan, M.J.1
  • 9
    • 58149088865 scopus 로고    scopus 로고
    • Discovery of multitarget inhibitors by combining molecular docking with common pharmacophore matching
    • Wei, D.; Jiang, X.; Zhou, L.; Chen, J.; Chen, Z.; He, C.; Yang, K.; Liu, Y.; Pei, J.; Lai, L. Discovery of multitarget inhibitors by combining molecular docking with common pharmacophore matching J. Med. Chem. 2008, 51, 7882
    • (2008) J. Med. Chem. , vol.51 , pp. 7882
    • Wei, D.1    Jiang, X.2    Zhou, L.3    Chen, J.4    Chen, Z.5    He, C.6    Yang, K.7    Liu, Y.8    Pei, J.9    Lai, L.10
  • 13
    • 84900442710 scopus 로고    scopus 로고
    • Pyrrolidine derivatives as dual NK1/NK3 receptor antagonists. PCT Int. Appl. WO2008128891.
    • Bissantz, C.; Hoffmann, T.; Jablonski, P.; Knust, H.; Nettekoven, M.; Ratni, H.; Wu, X. Pyrrolidine derivatives as dual NK1/NK3 receptor antagonists. PCT Int. Appl., WO2008128891, 2008.
    • (2008)
    • Bissantz, C.1    Hoffmann, T.2    Jablonski, P.3    Knust, H.4    Nettekoven, M.5    Ratni, H.6    Wu, X.7
  • 17
    • 11144336770 scopus 로고    scopus 로고
    • Synthetic preparation of N -methyl-α-amino acids
    • Aurelio, L.; Brownlee, R. T. C.; Hughes, A. B. Synthetic preparation of N -methyl-α-amino acids Chem. Rev. 2004, 104, 5823
    • (2004) Chem. Rev. , vol.104 , pp. 5823
    • Aurelio, L.1    Brownlee, R.T.C.2    Hughes, A.B.3
  • 22
    • 0027512532 scopus 로고
    • A facile synthesis of the novel Neurokinin A antagonist SR 48968
    • Hale, J. J.; Finke, P. E.; MacCoss, M. A facile synthesis of the novel Neurokinin A antagonist SR 48968 Bioorg. Med. Chem. Lett. 1993, 3, 319
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 319
    • Hale, J.J.1    Finke, P.E.2    Maccoss, M.3
  • 23
  • 24
    • 80052328305 scopus 로고    scopus 로고
    • Enantioselective α-arylation of N -acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts
    • Bigot, A.; Williamson, A. E.; Gaunt, M. J. Enantioselective α-arylation of N -acyloxazolidinones with copper(II)-bisoxazoline catalysts and diaryliodonium salts J. Am. Chem. Soc. 2011, 133, 13778
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 13778
    • Bigot, A.1    Williamson, A.E.2    Gaunt, M.J.3
  • 25
    • 77956083484 scopus 로고    scopus 로고
    • Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: Stereoconvergent suzuki reactions of racemic acylated halohydrins
    • Owston, N. A.; Fu, G. C. Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent suzuki reactions of racemic acylated halohydrins J. Am. Chem. Soc. 2010, 132, 11908
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11908
    • Owston, N.A.1    Fu, G.C.2
  • 26
    • 77955573357 scopus 로고    scopus 로고
    • Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: Arylations of racemic α-chloroamides
    • Lundin, P. M.; Fu, G. C. Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic α-chloroamides J. Am. Chem. Soc. 2010, 132, 11027
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11027
    • Lundin, P.M.1    Fu, G.C.2
  • 28
    • 41449104100 scopus 로고    scopus 로고
    • Catalytic asymmetric Hiyama cross-couplings of racemic α-bromo esters
    • Dai, X.; Strotman, N. A.; Fu, G. C. Catalytic asymmetric Hiyama cross-couplings of racemic α-bromo esters J. Am. Chem. Soc. 2008, 130, 3302
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 3302
    • Dai, X.1    Strotman, N.A.2    Fu, G.C.3
  • 29
    • 53349112702 scopus 로고
    • Mono-protected diamines. N - Tert -Butoxycarbonyl-α, -alkanediamines from α, -alkanediamines
    • Krapcho, A. P.; Kuell, C. S. Mono-protected diamines. N-tert -Butoxycarbonyl-α,I-alkanediamines from α,I-alkanediamines Synth. Commun. 1990, 20, 2559
    • (1990) Synth. Commun. , vol.20 , pp. 2559
    • Krapcho, A.P.1    Kuell, C.S.2
  • 31
    • 33845349490 scopus 로고    scopus 로고
    • Effective methods for the synthesis of N -methyl β - amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones
    • Hughes, A. B.; Sleebs, B. E. Effective methods for the synthesis of N -methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones Helv. Chim. Acta 2006, 89, 2611
    • (2006) Helv. Chim. Acta , vol.89 , pp. 2611
    • Hughes, A.B.1    Sleebs, B.E.2
  • 32
    • 0002840747 scopus 로고
    • Synthesis of 9-fluorenylmethyloxycarbonyl-protected N -alkyl amino acids by reduction of oxazolidinones
    • Freidinger, R. M.; Hinkle, J. S.; Perlow, D. S.; Arison, B. H. Synthesis of 9-fluorenylmethyloxycarbonyl-protected N -alkyl amino acids by reduction of oxazolidinones J. Org. Chem. 1983, 48, 77
    • (1983) J. Org. Chem. , vol.48 , pp. 77
    • Freidinger, R.M.1    Hinkle, J.S.2    Perlow, D.S.3    Arison, B.H.4
  • 33
    • 84862869077 scopus 로고    scopus 로고
    • Fragment-based approaches in drug discovery and chemical biology
    • Scott, D. E.; Coyne, A. G.; Hudson, S. A.; Abell, C. Fragment-based approaches in drug discovery and chemical biology Biochemistry 2012, 51, 4990
    • (2012) Biochemistry , vol.51 , pp. 4990
    • Scott, D.E.1    Coyne, A.G.2    Hudson, S.A.3    Abell, C.4
  • 34
    • 49549139072 scopus 로고
    • Reactifs de couplage peptidique i (1)-l′hexafluorophosphate de benzotriazolyl N -oxytrisdimethylamino phosphonium (B.O.P.)
    • Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Reactifs de couplage peptidique I (1)-l′hexafluorophosphate de benzotriazolyl N -oxytrisdimethylamino phosphonium (B.O.P.) Tetrahedron Lett. 1979, 16, 1219
    • (1979) Tetrahedron Lett. , vol.16 , pp. 1219
    • Castro, B.1    Dormoy, J.R.2    Evin, G.3    Selve, C.4
  • 35
    • 0000441415 scopus 로고
    • Rhodium(I)- and iridium(I)-catalyzed hydroboration reactions: Scope and synthetic applications
    • Evans, D. A.; Fu, G. C.; Hoveyda, A. H. Rhodium(I)- and iridium(I)-catalyzed hydroboration reactions: scope and synthetic applications J. Am. Chem. Soc. 1992, 114, 6671
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6671
    • Evans, D.A.1    Fu, G.C.2    Hoveyda, A.H.3
  • 36
    • 0000526264 scopus 로고
    • Mechanistic study of the rhodium(I)-catalyzed hydroboration reaction
    • Evans, D. A.; Fu, G. C.; Anderson, B. A. Mechanistic study of the rhodium(I)-catalyzed hydroboration reaction J. Am. Chem. Soc. 1992, 114, 6679
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6679
    • Evans, D.A.1    Fu, G.C.2    Anderson, B.A.3
  • 37
    • 3042741556 scopus 로고
    • A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species
    • Dess, D. B.; Martin, J. C. A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species J. Am. Chem. Soc. 1991, 113, 7277
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277
    • Dess, D.B.1    Martin, J.C.2
  • 38
    • 33644528891 scopus 로고
    • Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
    • Dess, D. B.; Martin, J. C. Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones J. Org. Chem. 1983, 48, 4155
    • (1983) J. Org. Chem. , vol.48 , pp. 4155
    • Dess, D.B.1    Martin, J.C.2
  • 39
    • 65549137900 scopus 로고    scopus 로고
    • Synthesis of 5-amino and 4-hydroxy-2-phenylsulfonylmethylpiperidines
    • Massé, J.; Langlois, N. Synthesis of 5-amino and 4-hydroxy-2-phenylsulfonylmethylpiperidines Heterocycles 2009, 77, 417
    • (2009) Heterocycles , vol.77 , pp. 417
    • Massé, J.1    Langlois, N.2
  • 40
    • 0034693175 scopus 로고    scopus 로고
    • Pd/C(en)-Catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations
    • Hattori, K.; Sajiki, H.; Hirota, K. Pd/C(en)-Catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations Tetrahedron 2000, 56, 8433
    • (2000) Tetrahedron , vol.56 , pp. 8433
    • Hattori, K.1    Sajiki, H.2    Hirota, K.3
  • 41
    • 53849102615 scopus 로고    scopus 로고
    • Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors
    • Boyer, N.; Gloanec, P.; De Nanteuil, G.; Jubault, P.; Quirion, J.-C. Synthesis of α,α-difluoro-β-amino esters or gem-difluoro-β-lactams as potential metallocarboxypeptidase inhibitors Eur. J. Org. Chem. 2008, 4277
    • (2008) Eur. J. Org. Chem. , pp. 4277
    • Boyer, N.1    Gloanec, P.2    De Nanteuil, G.3    Jubault, P.4    Quirion, J.-C.5
  • 42
    • 33845437508 scopus 로고    scopus 로고
    • Synthesis of 3,3-disubstituted oxindoles
    • Liu, K. G.; Robichaud, A. J. Synthesis of 3,3-disubstituted oxindoles Tetrahedron Lett. 2007, 48, 461
    • (2007) Tetrahedron Lett. , vol.48 , pp. 461
    • Liu, K.G.1    Robichaud, A.J.2
  • 43
    • 33749314877 scopus 로고    scopus 로고
    • An efficient synthesis of a spirocyclic oxindole analogue
    • Teng, D.; Zhang, H.; Mendonca, A. An efficient synthesis of a spirocyclic oxindole analogue Molecules 2006, 11, 700
    • (2006) Molecules , vol.11 , pp. 700
    • Teng, D.1    Zhang, H.2    Mendonca, A.3
  • 45
    • 0034125221 scopus 로고    scopus 로고
    • A convenient synthetic route to spiro[indole-3,4′-piperidin]-2-ones
    • Freund, R. A convenient synthetic route to spiro[indole-3,4′- piperidin]-2-ones Helv. Chim. Acta 2000, 83, 1247
    • (2000) Helv. Chim. Acta , vol.83 , pp. 1247
    • Freund, R.1
  • 50
    • 33750116951 scopus 로고    scopus 로고
    • A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes
    • Abdel-Magid, A. F.; Mehrman, S. J. A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes Org. Process Res. Dev. 2006, 10, 971
    • (2006) Org. Process Res. Dev. , vol.10 , pp. 971
    • Abdel-Magid, A.F.1    Mehrman, S.J.2
  • 51
    • 0000844109 scopus 로고    scopus 로고
    • Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride studies on direct and indirect reductive amination procedures
    • Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. studies on direct and indirect reductive amination procedures J. Org. Chem. 1996, 61, 3849
    • (1996) J. Org. Chem. , vol.61 , pp. 3849
    • Abdel-Magid, A.F.1    Carson, K.G.2    Harris, B.D.3    Maryanoff, C.A.4    Shah, R.D.5
  • 52
    • 35048885691 scopus 로고    scopus 로고
    • Chiral counteranions in asymmetric transition-metal catalysis: Highly enantioselective Pd/Brønsted acid-catalyzed direct α-allylation of aldehydes
    • Mukherjee, S.; List, B. Chiral counteranions in asymmetric transition-metal catalysis: highly enantioselective Pd/Brønsted acid-catalyzed direct α-allylation of aldehydes J. Am. Chem. Soc. 2007, 129, 11336
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 11336
    • Mukherjee, S.1    List, B.2
  • 53
    • 0037051609 scopus 로고    scopus 로고
    • Nickel-BINAP catalyzed enantioselective α-arylation of α-substituted γ-butyrolactones
    • Spielvogel, D. J.; Buchwald, S. L. Nickel-BINAP catalyzed enantioselective α-arylation of α-substituted γ-butyrolactones J. Am. Chem. Soc. 2002, 124, 3500
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3500
    • Spielvogel, D.J.1    Buchwald, S.L.2
  • 54
    • 0000265129 scopus 로고
    • Asymmetric construction of quaternary carbons from chiral malonates: Selective and versatile total syntheses of the enantiomers of α- And β-cuparenones from a common optically active precursor
    • Canet, J.-L.; Fadel, A.; Salaün, J. Asymmetric construction of quaternary carbons from chiral malonates: selective and versatile total syntheses of the enantiomers of α- and β-cuparenones from a common optically active precursor J. Org. Chem. 1992, 57, 3463
    • (1992) J. Org. Chem. , vol.57 , pp. 3463
    • Canet, J.-L.1    Fadel, A.2    Salaün, J.3
  • 56
    • 0021159751 scopus 로고
    • O -Benzotriazolyl- N, N, N ′, N ′-tetramethyluronium hexafluorophosphate as coupling reagent for the synthesis of peptides of biological interest
    • Dourtoglou, V.; Gross, B.; Lambropoulou, V.; Zioudrou, C. O -Benzotriazolyl- N, N, N ′, N ′-tetramethyluronium hexafluorophosphate as coupling reagent for the synthesis of peptides of biological interest Synthesis 1984, 572
    • (1984) Synthesis , pp. 572
    • Dourtoglou, V.1    Gross, B.2    Lambropoulou, V.3    Zioudrou, C.4
  • 57
    • 0025014627 scopus 로고
    • PyBOP: A new peptide coupling reagent devoid of toxic by-product
    • Coste, J.; Le-Nguyen, D.; Castro, B. PyBOP: a new peptide coupling reagent devoid of toxic by-product Tetrahedron Lett. 1990, 31, 205
    • (1990) Tetrahedron Lett. , vol.31 , pp. 205
    • Coste, J.1    Le-Nguyen, D.2    Castro, B.3
  • 59
    • 78649852683 scopus 로고    scopus 로고
    • Chemical modifications designed to improve peptide stability: Incorporation of non-natural amino acids, pseudo-peptide bonds, and cyclization
    • Gentilucci, L.; De Marco, R.; Cerisoli, L. Chemical modifications designed to improve peptide stability: incorporation of non-natural amino acids, pseudo-peptide bonds, and cyclization Curr. Pharm. Des. 2010, 16, 3185
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 3185
    • Gentilucci, L.1    De Marco, R.2    Cerisoli, L.3
  • 60
    • 70350173842 scopus 로고    scopus 로고
    • Peptidomimetics: A versatile route to biologically active compounds
    • Grauer, A.; König, B. Peptidomimetics: a versatile route to biologically active compounds Eur. J. Org. Chem. 2009, 5099
    • (2009) Eur. J. Org. Chem. , pp. 5099
    • Grauer, A.1    König, B.2


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