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Volumn 6, Issue 3-4, 2003, Pages 227-235

Passerini reaction - Amine Deprotection - Acyl Migration (PADAM): A convenient strategy for the solid-phase preparation of peptidomimetic compounds

Author keywords

Multicomponent reactions; N Boc aminoaldehydes; Passerini reaction; Peptidomimetics; Photocleavable linker; Protease inhibitors; Solid phase synthesis

Indexed keywords

9 FLUORENYLMETHYL CHLOROFORMATE; AMINE; AMINOALDEHYDE; BETA ACYLAMINO ALPHA HYDROXYAMIDE; CARBOXYLIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; POLYSTYRENE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0345871014     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000006778.42751.7f     Document Type: Conference Paper
Times cited : (44)

References (25)
  • 1
    • 0032035067 scopus 로고    scopus 로고
    • Isocyanide based multi component reactions in combinatorial chemistry
    • Dömling, A., Isocyanide based multi component reactions in combinatorial chemistry, Comb. Chem. High Throughput Screening, 1 (1998) 1-22.
    • (1998) Comb. Chem. High Throughput Screening , vol.1 , pp. 1-22
    • Dömling, A.1
  • 2
    • 2542509173 scopus 로고    scopus 로고
    • Multicomponent reactions with isocyanides
    • Dömling, A. and Ugi, I., Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. Engl., 39 (2000) 3169-3210.
    • (2000) Angew. Chem. Int. Ed. Engl. , vol.39 , pp. 3169-3210
    • Dömling, A.1    Ugi, I.2
  • 3
    • 0037079610 scopus 로고    scopus 로고
    • Multi-component reactions and evolutionary chemistry
    • Weber, L., multi-component reactions and evolutionary chemistry, Drug Discovery Today, 7 (2002) 143-147.
    • (2002) Drug Discovery Today , vol.7 , pp. 143-147
    • Weber, L.1
  • 4
    • 0034665244 scopus 로고    scopus 로고
    • Maximizing synthetic efficiency: Multi-component transformations lead the way
    • Bienaymé, H., Hulme, C., Oddon, G. and Schmitt, P., Maximizing synthetic efficiency: Multi-component transformations lead the way, Chem. Eur. J., 6 (2000) 3321-3329.
    • (2000) Chem. Eur. J. , vol.6 , pp. 3321-3329
    • Bienaymé, H.1    Hulme, C.2    Oddon, G.3    Schmitt, P.4
  • 5
    • 0345738470 scopus 로고
    • The Passerini condensation was discovered in Florence by Mario Passerini in 1921; [6,7] unfortunately his first reports were written in italian on the Gazzetta Chimica Italiana, and the scientific comunity became aware of this reaction only after Ivar Ugi published, in 1960, the first report [8] on its famous four component condensation between an aldehyde, a carboxylic acid, an isocyanide and an amine, the first three compounds being the ingredients of the Passerini reaction.
    • (1921) Gazzetta Chimica Italiana
    • Passerini, M.1
  • 6
    • 0001685385 scopus 로고
    • Sopra gli Isonitrili (I). Composto del p-Isonitrilazobenzolo con Acetone ed Acido Acetico
    • Passerini, M., Sopra gli Isonitrili (I). Composto del p-Isonitrilazobenzolo con Acetone ed Acido Acetico, Gazz. Chim. Ital., 51-2 (1921) 126-129.
    • (1921) Gazz. Chim. Ital. , vol.51-52 , pp. 126-129
    • Passerini, M.1
  • 7
    • 0001347708 scopus 로고
    • Sopra gli Isonitrili (II). Composti con Aldeidi o con Chetoni ed Acidi Organici Monobasici
    • Passerini, M., Sopra gli Isonitrili (II). Composti con Aldeidi o con Chetoni ed Acidi Organici Monobasici, Gazz. Chim. Ital., 51-2 (1921) 181-188.
    • (1921) Gazz. Chim. Ital. , vol.51-52 , pp. 181-188
    • Passerini, M.1
  • 8
    • 0001008510 scopus 로고
    • Über ein neues Kondensations-Prinzip
    • Ugi, I. and Steinbrueckner, C., Über ein neues Kondensations-Prinzip, Angew. Chem., 72 (1960) 267-268.
    • (1960) Angew. Chem. , vol.72 , pp. 267-268
    • Ugi, I.1    Steinbrueckner, C.2
  • 9
    • 0030939020 scopus 로고    scopus 로고
    • Exploitation of the Ugi 4CC Reaction: Preparation of Small Molecule Combinatorial Libraries via Solid Phase
    • see for example: Short, K. M., Ching, B. W. and Mjalli, A. M. M., Exploitation of the Ugi 4CC Reaction: Preparation of Small Molecule Combinatorial Libraries via Solid Phase, Tetrahedron, 53 (1997) 6653-6679.
    • (1997) Tetrahedron , vol.53 , pp. 6653-6679
    • Short, K.M.1    Ching, B.W.2    Mjalli, A.M.M.3
  • 10
    • 0032578740 scopus 로고    scopus 로고
    • Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy
    • see for example: Hulme, C., Peng, J., Louridas, B., Menard, P., Krolikowski, P. and Kumar, N. V., Applications of N-BOC-diamines for the solution phase synthesis of ketopiperazine libraries utilizing a Ugi/De-BOC/Cyclization (UDC) strategy, Tetrahedron Lett., 39 (1998) 8047-8050.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8047-8050
    • Hulme, C.1    Peng, J.2    Louridas, B.3    Menard, P.4    Krolikowski, P.5    Kumar, N.V.6
  • 11
    • 84952146812 scopus 로고
    • Studies on Isocyanides and Related Compounds. Synthesis of Oxazole Derivatives via the Passerini Reaction
    • see for example: Bossio, R., Marcaccini, S. and Pepino, R., Studies on Isocyanides and Related Compounds. Synthesis of Oxazole Derivatives via the Passerini Reaction, Liebigs Ann. Chem., 10 (1991) 1107-1108.
    • (1991) Liebigs Ann. Chem. , vol.10 , pp. 1107-1108
    • Bossio, R.1    Marcaccini, S.2    Pepino, R.3
  • 12
    • 0034616838 scopus 로고    scopus 로고
    • Passerini multicomponent reaction of protected alpha-aminoaldehydes as a tool for combinatorial synthesis of enzyme inhibitors
    • Banfi, L., Guanti, G. and Riva, R., Passerini multicomponent reaction of protected alpha-aminoaldehydes as a tool for combinatorial synthesis of enzyme inhibitors, Chem. Comm., (2000) 985-986.
    • (2000) Chem. Comm. , pp. 985-986
    • Banfi, L.1    Guanti, G.2    Riva, R.3
  • 13
    • 0035801852 scopus 로고    scopus 로고
    • Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy
    • Owens, T. D., Araldi, G.-L., Nutt, R. F. and Semple, J. E., Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy, Tetrahedron Lett., 42 (2001) 6271-6274.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6271-6274
    • Owens, T.D.1    Araldi, G.-L.2    Nutt, R.F.3    Semple, J.E.4
  • 14
    • 0343433408 scopus 로고    scopus 로고
    • Cysteine proteases and their inhibitors
    • Otto, H.-H. and Schirmeister, T., Cysteine proteases and their inhibitors, Chem. Rev., 97 (1997) 133-171.
    • (1997) Chem. Rev. , vol.97 , pp. 133-171
    • Otto, H.-H.1    Schirmeister, T.2
  • 15
    • 0032087776 scopus 로고    scopus 로고
    • Discovery of protease inhibitors using targeted libraries
    • Whittaker, M., Discovery of protease inhibitors using targeted libraries, Curr. Opin. Chem. Biol., 2 (1998) 386-396.
    • (1998) Curr. Opin. Chem. Biol. , vol.2 , pp. 386-396
    • Whittaker, M.1
  • 16
    • 0037430642 scopus 로고    scopus 로고
    • Solid-phase synthesis of modified oligopeptides via Passerini multicomponent reaction
    • Basso, A., Banfi, L., Riva, R., Piaggio, P. and Guanti, G., Solid-phase synthesis of modified oligopeptides via Passerini multicomponent reaction, Tetrahedron Lett., 44 (2003) 2367-2370.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2367-2370
    • Basso, A.1    Banfi, L.2    Riva, R.3    Piaggio, P.4    Guanti, G.5
  • 17
    • 0033683359 scopus 로고    scopus 로고
    • Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry
    • Guillier, F., Orain, D. and Bradley, M., Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry, Chem. Rev., 100 (2000) 2091-2157.
    • (2000) Chem. Rev. , vol.100 , pp. 2091-2157
    • Guillier, F.1    Orain, D.2    Bradley, M.3
  • 18
    • 0001294786 scopus 로고
    • Convergent solid phase peptide synthesis. II. Synthesis of the 1-6 apamin protected segment on a NBB-resin. Synthesis of apamin
    • Giralt, E., Albericio, F., Pedroso, E., Granier, C. and van Rietschoten, J., Convergent solid phase peptide synthesis. II. Synthesis of the 1-6 apamin protected segment on a NBB-resin. Synthesis of apamin, Tetrahedron, 38 (1982) 1193-1201.
    • (1982) Tetrahedron , vol.38 , pp. 1193-1201
    • Giralt, E.1    Albericio, F.2    Pedroso, E.3    Granier, C.4    Van Rietschoten, J.5
  • 19
    • 0034898816 scopus 로고    scopus 로고
    • Multi-component synthesis of imidazo[1,2-a] annulated heterocycles on alpha-isocyano resin esters
    • Chen, J. J., Golebiowski, A., Klopfenstein, S. R., J., M., Peng, S. X., Portlock, D. E. and West, L., Multi-component synthesis of imidazo[1,2-a] annulated heterocycles on alpha-isocyano resin esters, Synlett, 8 (2001) 1263-1265.
    • (2001) Synlett , vol.8 , pp. 1263-1265
    • Chen, J.J.1    Golebiowski, A.2    Klopfenstein, S.R.J.M.3    Peng, S.X.4    Portlock, D.E.5    West, L.6
  • 20
    • 0030059786 scopus 로고    scopus 로고
    • Synthesis of Tetrasubstituted Imidazoles via [alpha]-(N-acyl-N-alkylamino)-[beta]-ketoamides on Wang Resin
    • Chengzhi, Z., Moran, E. J., Woiwode, T. F., Short, K. M. and Mjalli, A. M. M., Synthesis of Tetrasubstituted Imidazoles via [alpha]-(N-acyl-N-alkylamino)-[beta]-ketoamides on Wang Resin, Tetrahedron Lett., 37 (1996) 751-754.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 751-754
    • Chengzhi, Z.1    Moran, E.J.2    Woiwode, T.F.3    Short, K.M.4    Mjalli, A.M.M.5
  • 21
    • 0033166824 scopus 로고    scopus 로고
    • A Solid-phase Equivalent of van Leusen's TosMIC, and its Application in Oxazole Synthesis
    • Kulkarni, B. A. and Ganesan, A., A Solid-phase Equivalent of van Leusen's TosMIC, and its Application in Oxazole Synthesis, Tetrahedron Lett., 40 (1999) 5633-5636.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5633-5636
    • Kulkarni, B.A.1    Ganesan, A.2
  • 22
    • 0025932811 scopus 로고
    • Albericio Fernando and Giralt, Ernest, Convergent solid-phase peptide synthesis. X. Synthesis and purification of protected peptide fragments using the photolabile Nbb-resin
    • Lloyd-Williams, P., Gairi, M., Albericio, Fernando and Giralt, Ernest, Convergent solid-phase peptide synthesis. X. Synthesis and purification of protected peptide fragments using the photolabile Nbb-resin., Tetrahedron, 47 (1991) 9867-9880.
    • (1991) Tetrahedron , vol.47 , pp. 9867-9880
    • Lloyd-Williams, P.1    Gairi, M.2
  • 23
    • 0000683556 scopus 로고    scopus 로고
    • Photoacoustic FTIR spectroscopy, a nondestructive method for sensitive analysis of solid-phase organic chemistry
    • Gosselin, F., Di Renzo, M., Ellis, T. H. and Lubell, W. D., Photoacoustic FTIR spectroscopy, a nondestructive method for sensitive analysis of solid-phase organic chemistry, J. Org. Chem., 61 (1996) 7980-7981.
    • (1996) J. Org. Chem. , vol.61 , pp. 7980-7981
    • Gosselin, F.1    Di Renzo, M.2    Ellis, T.H.3    Lubell, W.D.4
  • 24
    • 0035901676 scopus 로고    scopus 로고
    • Oxoammonium resins as metal-free, highly reactive, versatile polymeric oxidation reagents
    • Weik, S., Nicholson, G., Jung, G. and Rademann, J., Oxoammonium resins as metal-free, highly reactive. versatile polymeric oxidation reagents, Angew. Chem. Int. Ed. Engl., 40 (2001) 1436-1439.
    • (2001) Angew. Chem. Int. Ed. Engl. , vol.40 , pp. 1436-1439
    • Weik, S.1    Nicholson, G.2    Jung, G.3    Rademann, J.4
  • 25
    • 0000234498 scopus 로고    scopus 로고
    • A simple and advantageous protocol for the oxidation of alcohols with, o-iodoxybenzoic acid (IBX)
    • More, J. D. and Finney, N. S., A simple and advantageous protocol for the oxidation of alcohols with, o-iodoxybenzoic acid (IBX), Organic Letters, 4 (2002) 3001-3003.
    • (2002) Organic Letters , vol.4 , pp. 3001-3003
    • More, J.D.1    Finney, N.S.2


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