Title of article :
Synthesis of amino acid esters of the ruthenium naphthalene complex [(C5Me4CH2OH)Ru(C10H8)]+
Author/Authors :
Perekalin، نويسنده , , Dmitry S. and Molotkov، نويسنده , , Alexander P. and Nelyubina، نويسنده , , Yulia V. and Anisimova، نويسنده , , Natalia Yu. and Kudinov، نويسنده , , Alexander R.، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2014
Abstract :
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 [(C5Me4CH2OOCCH(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 [(η5-C5Me4)CH2OOCCH(CH2-η6-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 μM) 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.
Keywords :
Ruthenium , cyclopentadienyl , naphthalene , amino acids , Bioorganometallic chemistry , Anticancer agents
Journal title :
INORGANICA CHIMICA ACTA
Journal title :
INORGANICA CHIMICA ACTA