Synthesis of amino acid esters of the ruthenium naphthalene complex [(C5Me4CH2OH)Ru(C10H8)]+

被引：12

作者：

Perekalin, Dmitry S. ^{[1
]}

Molotkov, Alexander P. ^{[1
]}

Nelyubina, Yulia V. ^{[1
]}

Anisimova, Natalia Yu ^{[2
]}

Kudinov, Alexander R. ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

[2] Russian Acad Med Sci, NN Blokhin Russian Canc Res Ctr, Moscow 115478, Russia

来源：

INORGANICA CHIMICA ACTA | 2014年 / 409卷

基金：

俄罗斯基础研究基金会;

关键词：

Ruthenium; Cyclopentadienyl; Naphthalene; Amino acids; Bioorganometallic chemistry; Anticancer agents; SANDWICH COMPLEXES; LIGANDS;

D O I：

10.1016/j.ica.2013.10.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Ruthenium naphthalene complex [(C5Me4CH2OH)Ru(C10H8)](+) (2) with hydroxy-substituted cyclopentadienyl ligand reacts with N-Boc-protected alanine, methionine, phenylalanine, and tryptophan in the presence of dicyclohexylcarbodiimide giving organometallic esters of amino acids [(C5Me4CH2-OOCCH(CH2R)NHBoc)Ru(C10H8)](+) (3a-d) in 70-86% yields. Irradiation of phenylalanine derivative 3c at 365 nm results in replacement of the naphthalene ligand by the phenyl group giving ansa-complex [(eta(5)-C5Me4)CH2OOCCH(CH2-eta(6)-Ph)NHBoc)Ru](+) (4) in 47% yield. Complexes [3c,d] BF4 containing phenylalanine and tryptophan residues effectively inhibit growth of cancer cell lines B16, MeWo, SCOV3, SKBR3, and A549 (IC50 = 21-96 mu M) with activity and selectivity being close to those of the cisplatin. The structure of the alanine derivative [3a]BPh4 was established by X-ray diffraction. (C) 2013 Elsevier B.V. All rights reserved.

引用

页码：390 / 393

页数：4

共 25 条

[1] Ruthenium half-sandwich complexes as protein kinase inhibitors:: An N-succinimidyl ester for rapid derivatizations of the cyclopentadienyl moiety [J].

Bregman, Howard ;

Meggers, Eric .

ORGANIC LETTERS, 2006, 8 (24) :5465-5468

[2] Arene binding affinities in [CpRu(η6-arene)]+ complexes:: Models for the adsorption of arenes on hydrodesulfurization catalysts [J].

Choi, Moon-Gun ;

Ho, Teh C. ;

Angelici, Robert J. .

ORGANOMETALLICS, 2008, 27 (06) :1098-1105

[3] [(η5-C5Me4CH2R)Ru(η6-arene)]+ and [η5-C5Me4CH2R)Ru(CH3CN)3]+ compounds possessing pendant arms [J].

Fairchild, Robert M. ;

Holman, K. Travis .

ORGANOMETALLICS, 2008, 27 (08) :1823-1833

[4] Ring-methyl activation in pentamethylcyclopentadienyl complexes .5. Syntheses and structures of tetramethylfulvene complexes of ruthenium(II) [J].

Fan, L ;

Wei, CH ;

Aigbirhio, FI ;

Turner, ML ;

Gusev, OV ;

Morozova, LN ;

Knowles, DRT ;

Maitlis, PM .

ORGANOMETALLICS, 1996, 15 (01) :98-104

[5] Organometallic Anticancer Compounds [J].

Gasser, Gilles ;

Ott, Ingo ;

Metzler-Nolte, Nils .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (01) :3-25

[6] Challenges and Opportunities in the Development of Organometallic Anticancer Drugs [J].

Hartinger, Christian G. ;

Metzler-Nolte, Nils ;

Dyson, Paul J. .

ORGANOMETALLICS, 2012, 31 (16) :5677-5685

[7] Bioorganometallic chemistry-from teaching paradigms to medicinal applications [J].

Hartinger, Christian G. ;

Dyson, Paul J. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) :391-401

[8] New ruthenium(II) mixed metallocene derived complexes: Synthesis, characterization by X-ray diffraction and evaluation on DNA interaction by atomic force microscopy [J].

Helena Garcia, M. ;

Valente, Andreia ;

Florindo, Pedro ;

Morais, Tania S. ;

Piedade, M. Fatima M. ;

Teresa Duarte, M. ;

Moreno, Virtudes ;

Aviles, Francesc X. ;

Loreno, Julia .

INORGANICA CHIMICA ACTA, 2010, 363 (14) :3765-3775

[9] Photochemical arene exchange in the naphthalene complex [CpRu(η6-C10H8)]+ [J].

Karslyan, E. E. ;

Perekalin, D. S. ;

Petrovskii, P. V. ;

Borisova, A. O. ;

Kudinov, A. R. .

RUSSIAN CHEMICAL BULLETIN, 2009, 58 (03) :585-588

[10] Arene ruthenium dichloro complexes containing isonicotinic ester ligands: Synthesis, molecular structure and cytotoxicity [J].

Khan, Farooq-Ahmad ;

Therrien, Bruno ;

Suess-Fink, Georg ;

Zava, Olivier ;

Dyson, Paul J. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 730 :49-56

← 1 2 3 →