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Volumn 37, Issue 3, 2009, Pages 537-541

Synthesis and characterization of new Pd(II) complexes of l-ethylphenylalanate

Author keywords

Cyclopalladation; Orthometallate; Phenylalanine

Indexed keywords

ACETONITRILE; COLLIDINE; ETHYLPHENYLALANATE; PALLADIUM COMPLEX; PHENYLALANINE; PIPERIDINE; PYRIDINE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

EID: 69249245335     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-009-0258-3     Document Type: Article
Times cited : (20)

References (35)
  • 1
    • 0030937048 scopus 로고    scopus 로고
    • Cyclopalladation of the primary amine (R)-(+)-1-(1-naphthyl)ethylamine: A new resolving agent for monodentate phosphines
    • DOI 10.1016/S0957-4166(97)00087-6, PII S0957416697000876
    • J Albert JM Cadena J Granell 1997 Cyclopalladation of the primary amine (R)-(+)-1-(1-naphthyl)ethylamine: a new resolving agent for monodentate phosphines Tetrahedron Asymmetry 8 991 994 10.1016/S0957-4166(97)00087-6 (Pubitemid 27163287)
    • (1997) Tetrahedron Asymmetry , vol.8 , Issue.7 , pp. 991-994
    • Albert, J.1    Cadena, J.M.2    Granell, J.3
  • 3
    • 33646112143 scopus 로고    scopus 로고
    • Synthesis and applications of optically active metallacycles derived from primary amines
    • 10.1016/j.jorganchem.2005.10.041
    • J Albert J Granell G Muller 2006 Synthesis and applications of optically active metallacycles derived from primary amines J Organomet Chem 691 2101 2106 10.1016/j.jorganchem.2005.10.041
    • (2006) J Organomet Chem , vol.691 , pp. 2101-2106
    • Albert, J.1    Granell, J.2    Muller, G.3
  • 4
    • 17144466749 scopus 로고    scopus 로고
    • Ferrocene compounds part XXXIII. Synthesis and characterization of amino acids containing skeletal 1,1-ferrocenylene unit
    • 10.1016/S0022-328X(03)00774-5
    • L Barisic V Rapic H Pritzkow G Pavlovic I Nemet 2003 Ferrocene compounds part XXXIII. Synthesis and characterization of amino acids containing skeletal 1,1-ferrocenylene unit J Organomet Chem 682 131 142 10.1016/S0022-328X(03)00774- 5
    • (2003) J Organomet Chem , vol.682 , pp. 131-142
    • Barisic, L.1    Rapic, V.2    Pritzkow, H.3    Pavlovic, G.4    Nemet, I.5
  • 5
    • 33749136881 scopus 로고    scopus 로고
    • Complexes of platinum(II) and palladium(II) with aminomethylphosphonic acid and glycylaminomethylphosphonic acid
    • doi: 10.1039/a607736f
    • Blaha T, Lukes I, Rohovec J, Hermann P (1997) Complexes of platinum(II) and palladium(II) with aminomethylphosphonic acid and glycylaminomethylphosphonic acid. J Chem Soc Dalton Trans 2621-2628. doi: 10.1039/a607736f
    • (1997) J Chem Soc Dalton Trans , pp. 2621-2628
    • Blaha, T.1    Lukes, I.2    Rohovec, J.3    Hermann, P.4
  • 6
    • 0034472076 scopus 로고    scopus 로고
    • Determination of enantiomer purity of β- and γ-amino acids by NMR analysis of diastereoisomeric palladium complexes
    • DOI 10.1002/1522-2675(20001220)83:12<3262::AID-HLCA3262>3.0.CO;2-P
    • A Bohm D Seebach 2000 Determination of enantiomer purity of β- and γ-amino acids by NMR analysis of diastereoisomeric palladium complexes Helv Chim Acta 83 3262 3277 10.1002/1522-2675(20001220)83:12<3262::AID- HLCA3262>3.0.CO;2-P (Pubitemid 32178912)
    • (2000) Helvetica Chimica Acta , vol.83 , Issue.12 , pp. 3262-3278
    • Bohm, A.1    Seebach, D.2
  • 7
    • 0039521807 scopus 로고    scopus 로고
    • Metal complexes of biologically important ligands, CXXIV [1]. NMR-Spectroscopic determination of the enantiomeric ratio of α-amino acids by use of a chiral orthometallated palladium complex
    • A Bohm T Hauck W Beck 1999 Metal complexes of biologically important ligands, CXXIV [1]. NMR-Spectroscopic determination of the enantiomeric ratio of α-amino acids by use of a chiral orthometallated palladium complex Z Naturforsch 54b 1360 1362
    • (1999) Z Naturforsch , vol.54 , pp. 1360-1362
    • Bohm, A.1    Hauck, T.2    Beck, W.3
  • 8
    • 16244376782 scopus 로고    scopus 로고
    • Crystal engineering based on preferred mirror image recognition in square planar Pd(II) complexes
    • B Calmuschi E Englert 2005 Crystal engineering based on preferred mirror image recognition in square planar Pd(II) complexes Cryst Eng Comm 7 171 176
    • (2005) Cryst Eng Comm , vol.7 , pp. 171-176
    • Calmuschi, B.1    Englert, E.2
  • 9
    • 14644430932 scopus 로고    scopus 로고
    • Resolution of β-aminophosphines with chiral cyclopalladated complexes
    • DOI 10.1016/j.jorganchem.2005.01.023, PII S0022328X05000549
    • JM Camus P Roy-GarcIa J Andrieu P Richard R Poli 2005 Resolution of β-aminophosphines with chiral cyclopalladated complexes J Organomet Chem 690 1659 1668 10.1016/j.jorganchem.2005.01.023 (Pubitemid 40320502)
    • (2005) Journal of Organometallic Chemistry , vol.690 , Issue.6 , pp. 1659-1668
    • Camus, J.-M.1    Garcia, P.R.2    Andrieu, J.3    Richard, P.4    Poli, R.5
  • 10
    • 0040997380 scopus 로고
    • Electrophilic aromatic substitution reactions by platinum(II) and palladium(II) chlorides on N, N-dimethylbenzylamines
    • 10.1021/ja01006a012
    • AC Cope EC Friedrich 1968 Electrophilic aromatic substitution reactions by platinum(II) and palladium(II) chlorides on N, N-dimethylbenzylamines J Am Chem Soc 90 909 913 10.1021/ja01006a012
    • (1968) J Am Chem Soc , vol.90 , pp. 909-913
    • Cope, A.C.1    Friedrich, E.C.2
  • 11
    • 21944441002 scopus 로고    scopus 로고
    • The potential of palladacycles: More than just precatalysts
    • DOI 10.1021/cr030681r
    • J Dupont CS Consorti J Spencer 2005 The potential of palladacycles: more than just precatalysts Chem Rev 105 2527 2572 10.1021/cr030681r (Pubitemid 40947954)
    • (2005) Chemical Reviews , vol.105 , Issue.6 , pp. 2527-2571
    • Dupont, J.1    Consorti, C.S.2    Spencer, J.3
  • 12
    • 0038002231 scopus 로고    scopus 로고
    • Bioorganometallic chemistry: Structural diversity of organometallic complexes with bioligands and molecular recognition studies of several supramolecular hosts with biomolecules, alkali-metal ions, and organometallic pharmaceuticals
    • 10.1021/om0300777
    • RH Fish G Jaouen 2003 Bioorganometallic chemistry: structural diversity of organometallic complexes with bioligands and molecular recognition studies of several supramolecular hosts with biomolecules, alkali-metal ions, and organometallic pharmaceuticals Organometallics 22 2166 2177 10.1021/om0300777
    • (2003) Organometallics , vol.22 , pp. 2166-2177
    • Fish, R.H.1    Jaouen, G.2
  • 13
    • 0029116883 scopus 로고
    • Metal complexes of biologically important ligands, LXXVIII. Synthesis of palladium complexes of ferrocenyl substituted amino acid derivatives
    • 10.1139/v95-143
    • D Freiesleben K Polborn C Robl K Sunkel W Beck 1995 Metal complexes of biologically important ligands, LXXVIII. Synthesis of palladium complexes of ferrocenyl substituted amino acid derivatives Can J Chem 73 1164 1174 10.1139/v95-143
    • (1995) Can J Chem , vol.73 , pp. 1164-1174
    • Freiesleben, D.1    Polborn, K.2    Robl, C.3    Sunkel, K.4    Beck, W.5
  • 14
    • 0003161814 scopus 로고
    • Cyclopalladation of secondary and primary benzylamines
    • 10.1016/0020-1693(94)04440-7
    • Y Fuchita H Tsuchiya A Miyafuji 1995 Cyclopalladation of secondary and primary benzylamines Inorg Chim Acta 233 91 96 10.1016/0020-1693(94)04440-7
    • (1995) Inorg Chim Acta , vol.233 , pp. 91-96
    • Fuchita, Y.1    Tsuchiya, H.2    Miyafuji, A.3
  • 15
    • 33748390756 scopus 로고    scopus 로고
    • Synthesis of optically active cyclopalladated complexes of primary benzylamine derivatives, (R)-(2)-2-phenylglycine methyl ester and (±)-l-phenylethylamine
    • doi: 10.1039/a608622e
    • Fuchita Y, Yoshinaga K, Ikeda Y, Kinoshita-Kawashima J (1997) Synthesis of optically active cyclopalladated complexes of primary benzylamine derivatives, (R)-(2)-2-phenylglycine methyl ester and (±)-l- phenylethylamine. J Chem Soc Dalton Trans 2495-2500. doi: 10.1039/a608622e
    • (1997) J Chem Soc Dalton Trans , pp. 2495-2500
    • Fuchita, Y.1    Yoshinaga, K.2    Ikeda, Y.3    Kinoshita-Kawashima, J.4
  • 16
    • 48949089457 scopus 로고    scopus 로고
    • Synthesis of the unnatural amino acid Nα-Nε-(ferrocene-1- acetyl)-l-lysine: A novel organometallic nuclease
    • 10.1016/j.jorganchem.2008.06.012
    • AM Gellett PW Huber PJ Higgins 2008 Synthesis of the unnatural amino acid Nα-Nε-(ferrocene-1-acetyl)-l-lysine: a novel organometallic nuclease J Organomet Chem 693 2959 2962 10.1016/j.jorganchem.2008.06.012
    • (2008) J Organomet Chem , vol.693 , pp. 2959-2962
    • Gellett, A.M.1    Huber, P.W.2    Higgins, P.J.3
  • 17
    • 34547862836 scopus 로고    scopus 로고
    • Synthesis, characterization and crystal structures of two cis/trans pyridine-cyclopalladated ferrocenylimine complexes
    • JF Gong C Xu YH Zhang Y Zhu W Yang-Jie 2007 Synthesis, characterization and crystal structures of two cis/trans pyridine-cyclopalladated ferrocenylimine complexes Transit Met Chem 32 1000 1004
    • (2007) Transit Met Chem , vol.32 , pp. 1000-1004
    • Gong, J.F.1    Xu, C.2    Zhang, Y.H.3    Zhu, Y.4    Yang-Jie, W.5
  • 18
    • 0034615133 scopus 로고    scopus 로고
    • Resolution of racemic Sb-chiral stibindoles using an optically active ortho-palladated benzylamine derivative, via their diastereomeric complexes
    • doi: 10.1039/a909200e
    • Kurita J, Usuda F, Yasuike S, Tsuchiya T, Tsuda Y, Kiuchi F, Hosoi S (2000) Resolution of racemic Sb-chiral stibindoles using an optically active ortho-palladated benzylamine derivative, via their diastereomeric complexes. Chem Commun (Camb) 191-192. doi: 10.1039/a909200e
    • (2000) Chem Commun (Camb) , pp. 191-192
    • Kurita, J.1    Usuda, F.2    Yasuike, S.3    Tsuchiya, T.4    Tsuda, Y.5    Kiuchi, F.6    Hosoi, S.7
  • 19
    • 0026028535 scopus 로고
    • Synthesis, characterization, DNA binding, and cytotoxic studies of some mixed-ligand palladium(II) and platinum(II) complexes of α-diimine and amino acids
    • 10.1016/0162-0134(91)80003-Z
    • R Mital TS Srivastava HK Parekh MP Chitnis 1991 Synthesis, characterization, DNA binding, and cytotoxic studies of some mixed-ligand palladium(II) and platinum(II) complexes of α-diimine and amino acids J Inorg Biochem 41 93 103 10.1016/0162-0134(91)80003-Z
    • (1991) J Inorg Biochem , vol.41 , pp. 93-103
    • Mital, R.1    Srivastava, T.S.2    Parekh, H.K.3    Chitnis, M.P.4
  • 20
    • 13444268124 scopus 로고
    • Platinum(II) and palladium(II) complexes with amino acid derivatives. Synthesis, interpretation of IR and 1H NMR spectra and conformational implications
    • 10.1016/S0020-1693(00)90793-X
    • S Mylonas A Valavanidis V Voukouvalidis 1981 Platinum(II) and palladium(II) complexes with amino acid derivatives. Synthesis, interpretation of IR and 1H NMR spectra and conformational implications Inorg Chim Acta 55 125 128 10.1016/S0020-1693(00)90793-X
    • (1981) Inorg Chim Acta , vol.55 , pp. 125-128
    • Mylonas, S.1    Valavanidis, A.2    Voukouvalidis, V.3
  • 21
    • 0037103033 scopus 로고    scopus 로고
    • Synthesis of Sb-chiral organoantimony compounds having intramolecular Sb-N interaction and their separation into optically pure compounds via ortho-palladated benzylamine complexes
    • DOI 10.1016/S0022-328X(02)01622-4, PII S0022328X02016224
    • Okajima S, Yasuike S, Kakusawa N, Osada A, Yamaguchi K, Seki H, Kurita (2002) Synthesis of Sb-chiral organoantimony compounds having intramolecular Sb-N interaction and their separation into optically pure compounds via ortho-palladated benzylamine complexes. J Organomet Chem 656:234-242. doi: 10.1016/S0022-328X(02)01622-4 (Pubitemid 34831044)
    • (2002) Journal of Organometallic Chemistry , vol.656 , Issue.1-2 , pp. 234-242
    • Okajima, S.1    Yasuike, S.2    Kakusawa, N.3    Osada, A.4    Yamaguchi, K.5    Seki, H.6    Kurita, J.7
  • 22
    • 4544321309 scopus 로고    scopus 로고
    • Coordination chemistry of 1, 3, 5-triaza-7-phosphaadamantane (PTA): Transition metal complexes and related catalytic, medicinal and photoluminescent applications
    • 10.1016/j.ccr.2004.05.011
    • I Omae 2004 Coordination chemistry of 1, 3, 5-triaza-7-phosphaadamantane (PTA): transition metal complexes and related catalytic, medicinal and photoluminescent applications Coord Chem Rev 248 955 993 10.1016/j.ccr.2004.05. 011
    • (2004) Coord Chem Rev , vol.248 , pp. 955-993
    • Omae, I.1
  • 23
    • 0027467523 scopus 로고
    • Some potential antitumor 2, 2-dipyridylamine Pt(II)/Pd(II) complexes with amino acids: Their synthesis, spectroscopy, DNA binding, and cytotoxic studies
    • 10.1016/0162-0134(93)80010-7
    • AK Paul H Mansuri-Torshizi TS Srivastava SJ Chavan MP Chitnis 1993 Some potential antitumor 2, 2-dipyridylamine Pt(II)/Pd(II) complexes with amino acids: their synthesis, spectroscopy, DNA binding, and cytotoxic studies J Inorg Biochem 50 9 20 10.1016/0162-0134(93)80010-7
    • (1993) J Inorg Biochem , vol.50 , pp. 9-20
    • Paul, A.K.1    Mansuri-Torshizi, H.2    Srivastava, T.S.3    Chavan, S.J.4    Chitnis, M.P.5
  • 24
    • 84950082606 scopus 로고
    • Selected applications to organic synthesis of intramolecular C-H activation reactions by transition metals
    • 10.1351/pac199264030335
    • M Pfeffer 1992 Selected applications to organic synthesis of intramolecular C-H activation reactions by transition metals Pure Appl Chem 64 335 342 10.1351/pac199264030335
    • (1992) Pure Appl Chem , vol.64 , pp. 335-342
    • Pfeffer, M.1
  • 25
    • 77749235787 scopus 로고
    • Cyclopalladated complexes in organic synthesis
    • doi: 10.1055/s-1985-31169
    • Ryabov AD (1985) Cyclopalladated complexes in organic synthesis. Synthesis 233-252. doi: 10.1055/s-1985-31169
    • (1985) Synthesis , pp. 233-252
    • Ryabov, A.D.1
  • 26
    • 0012671834 scopus 로고
    • Some complexes of palladium(II) with C-phenylglycine and its derivatives. Cyclopalladation of N, N-dimethyl-C-phenylglycine ethyl ester
    • 10.1016/S0020-1693(00)84220-6
    • AD Ryabov VA Polyakov AK Yatsimirsky 1984 Some complexes of palladium(II) with C-phenylglycine and its derivatives. Cyclopalladation of N, N-dimethyl-C-phenylglycine ethyl ester Inorg Chim Acta 91 59 65 10.1016/S0020-1693(00)84220-6
    • (1984) Inorg Chim Acta , vol.91 , pp. 59-65
    • Ryabov, A.D.1    Polyakov, V.A.2    Yatsimirsky, A.K.3
  • 27
    • 37049087521 scopus 로고
    • Kinetics and mechanism of halogen-bridge cleavage in dimethylaminomethylphenyl-C,N pallada- and platina-cycles by pyridines. Pressure effects, and crystal structures of the N,N-cis reaction product, its N,N-trans orthometallated analogue and a dimer of similar reactivity
    • doi: 10.1039/dt9950000999
    • Ryabov AD, Kuzmina LG, Polyakov VA, Kazankov GM, Ryabova ES, Pfeffer M, van Eldik R (1995) Kinetics and mechanism of halogen-bridge cleavage in dimethylaminomethylphenyl-C,N pallada- and platina-cycles by pyridines. Pressure effects, and crystal structures of the N,N-cis reaction product, its N,N-trans orthometallated analogue and a dimer of similar reactivity. J Chem Soc Dalton Trans 999-1006. doi: 10.1039/dt9950000999
    • (1995) J Chem Soc Dalton Trans , pp. 999-1006
    • Ryabov, A.D.1    Kuzmina, L.G.2    Polyakov, V.A.3    Kazankov, G.M.4    Ryabova, E.S.5    Pfeffer, M.6    Van Eldik, R.7
  • 28
    • 0032479389 scopus 로고    scopus 로고
    • Bioorganometallic chemistry-transition metal complexes with α-amino acids and peptides
    • DOI 10.1002/(SICI)1521-3773(19980703)37:12<1634::AID-ANIE1634>3.0. CO;2-C
    • K Severin R Bergs W Beck 1998 Bioorganometallic chemistry-transition metal complexes with α-amino acids and peptides Angew Chem Int Ed Engl 37 1634 1654 10.1002/(SICI)1521-3773(19980703)37:12<1634::AID-ANIE1634>3.0. CO;2-C (Pubitemid 28348534)
    • (1998) Angewandte Chemie - International Edition , vol.37 , Issue.12 , pp. 1634-1654
    • Severin, K.1    Bergs, R.2    Beck, W.3
  • 29
    • 37049084917 scopus 로고
    • The first orthopalladation of a primary nitrobenzylamine. Synthesis of chiral cyclopalladated complexes derived from (S)-±- methyl-4- nitrobenzylamine
    • doi: 10.1039/dt9950002535
    • Vicente J, Saura-Llamas I, Palin MG, Jones PG (1995) The first orthopalladation of a primary nitrobenzylamine. Synthesis of chiral cyclopalladated complexes derived from (S)-±- methyl-4-nitrobenzylamine. J Chem Soc Dalton Trans 2535-2539. doi: 10.1039/dt9950002535
    • (1995) J Chem Soc Dalton Trans , pp. 2535-2539
    • Vicente, J.1    Saura-Llamas, I.2    Palin, M.G.3    Jones, P.G.4
  • 30
    • 0001509959 scopus 로고    scopus 로고
    • Orthometallation of primary amines. 4. Orthopalladation of primary benzylamines and (2-phenylethyl)amine
    • 10.1021/om9609574
    • J Vicente I Saura-Llamas MG Palin PG Jones MC de Ramírez Arellano 1997 Orthometallation of primary amines. 4. Orthopalladation of primary benzylamines and (2-phenylethyl)amine Organometallics 16 826 833 10.1021/om9609574
    • (1997) Organometallics , vol.16 , pp. 826-833
    • Vicente, J.1    Saura-Llamas, I.2    Palin, M.G.3    Jones, P.G.4    De Ramírez Arellano, M.C.5
  • 31
    • 0347568508 scopus 로고    scopus 로고
    • Ortho-metalated primary amines. 6. the first synthesis of six-membered palladacycles from primary amines containing electron-withdrawing substituents: End of the limiting rules of Cope and Friedrich on cyclopalladation of benzyl- and phenethylamines
    • 10.1021/om030480d
    • J Vicente I Saura-Llamas J Cuadrado MC de Ramírez Arellano 2003 Ortho-metalated primary amines. 6. The first synthesis of six-membered palladacycles from primary amines containing electron-withdrawing substituents: end of the limiting rules of Cope and Friedrich on cyclopalladation of benzyl- and phenethylamines Organometallics 22 5513 5517 10.1021/om030480d
    • (2003) Organometallics , vol.22 , pp. 5513-5517
    • Vicente, J.1    Saura-Llamas, I.2    Cuadrado, J.3    De Ramírez Arellano, M.C.4
  • 32
    • 28944448163 scopus 로고    scopus 로고
    • Regiospecific functionalization of pharmaceuticals and other biologically active molecules through cyclopalladated compounds. 2-Iodination of phentermine and l-tryptophan methyl ester
    • 10.1021/om0506522
    • J Vicente I Saura-Llamas D Bautista 2005 Regiospecific functionalization of pharmaceuticals and other biologically active molecules through cyclopalladated compounds. 2-Iodination of phentermine and l-tryptophan methyl ester Organometallics 24 6001 6004 10.1021/om0506522
    • (2005) Organometallics , vol.24 , pp. 6001-6004
    • Vicente, J.1    Saura-Llamas, I.2    Bautista, D.3
  • 33
    • 34249065461 scopus 로고    scopus 로고
    • Ortho palladation and functionalization of L-phenylalanine methyl ester
    • DOI 10.1021/om070127y
    • J Vicente I Saura-Llamas JA Garcia-Lopez B Calmuschi-Cula D Bautista 2007 Orthopalladation and functionalization of l-phenylalanine methyl ester Organometallics 26 2768 2776 10.1021/om070127y (Pubitemid 46787371)
    • (2007) Organometallics , vol.26 , Issue.10 , pp. 2768-2776
    • Vicente, J.1    Saura-Llamas, I.2    Garcia-Lopez, J.-A.3    Calmuschi-Cula, B.4    Bautista, D.5
  • 34
    • 0031267871 scopus 로고    scopus 로고
    • Resolutions of tertiary phosphines and arsines with orthometallated palladium(II) amine complexes
    • DOI 10.1016/S0010-8545(97)00046-5
    • SB Wild 1997 Resolutions of tertiary phosphines and arsines with orthometallated palladium(II)-amine complexes Coord Chem Rev 166 291 311 10.1016/S0010-8545(97)00046-5 (Pubitemid 128021935)
    • (1997) Coordination Chemistry Reviews , vol.166 , pp. 291-312
    • Wild, S.B.1
  • 35
    • 0006955648 scopus 로고    scopus 로고
    • Pd(II) and Pt(II) complexes of 2-phenyl- and 2-benzyl-imidazoline: Synthesis, structural characterization, DNA modification and in vitro antileukaemic activity
    • 10.1002/(SICI)1099-0739(199708)11:8<659::AID-AOC614>3.0.CO;2-B
    • F Zamora VM Gonzalez JM Perez JR Masaguer C Navarro Ranninger 1997 Pd(II) and Pt(II) complexes of 2-phenyl- and 2-benzyl-imidazoline: synthesis, structural characterization, DNA modification and in vitro antileukaemic activity Appl Organomet Chem 11 659 666 10.1002/(SICI)1099-0739(199708)11: 8<659::AID-AOC614>3.0.CO;2-B
    • (1997) Appl Organomet Chem , vol.11 , pp. 659-666
    • Zamora, F.1    Gonzalez, V.M.2    Perez, J.M.3    Masaguer, J.R.4    Navarro Ranninger, C.5


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