Hetarylamidines derived from PtIV-mediated coupling of nitriles with aminoheterocycles

Abstract

The trans [PtCl 4 (EtCN) 2 ] complex is involved in coupling reactions (CH 2 Cl 2 , 30-35 °C, 10-15 min) with 2 amino derivatives of heterocyclic compounds (2 NH 2 Het, where Het is pyridyl, 4 methylpyridyl, 5 methylpyridyl, 6 methylpyridyl, or thiazolyl) to form the trans [PtCl 4 {N(H)=C(Et)NHHet} 2 ] complexes (1-5) with κ 1 (N ) coordinated hetarylamidine ligands. The reaction with the use of 2 aminopyrimidine (2 NH 2 Pym) produces the [PtCl 4 (2 NH 2 Pym) 2 ] complex (6) as a result of complete replacement of the nitrile ligands in the [PtCl 4 (EtCN) 2 ] complex. The compositions and structures of compounds 1-6 were con firmed by elemental analysis (C, H, N), IR spectroscopy, 1 H, 13 C{ 1 H}, and 195 Pt{ 1 H} NMR spectroscopy, and FAB mass spectrometry. Complex 1 was additionally characterized by X ray diffraction.

A New Class of Antitumortrans-Amine-Amidine-Pt(II) Cationic Complexes: Influence of Chemical Structure and Solvent on in Vitro and in Vivo Tumor Cell Proliferation

“…This value was in agreement with what was reported for one of the two crystalline forms of trans -[Pt(Pr i NH 2 ) 2 { Z -N(H)C(NHPr i )Me} 2 ][Cl 2 ], with a Pt−N(amidine) distance of 1.988(7) Å. The other one had an Pt−N(amidine) bond distance of 2.035(8) Å, which is comparable to the reported values of Pt−N bonds in [Pt(NHSPh 2 ) 2 {NHC(Me)NSPh 2 } 2 ][PF 6 ] and trans -[PtCl 4 {N(H)C(Et)(NHC 5 H 4 N)} 2 ] …”

“…The N(2)-C(4) and N(3)-C(4) bond distances were 1.297(6) and 1.341(7) Å , respectively, suggesting the presence of an electronic delocalization along the N-C-N system. The C-N bond distances were in the range that has been observed for trans-bis-amidine complexes such as 84 Solution Behavior. To improve the solubility, 85 the biological activity of the amidine complexes 1-3 was investigated by dissolving them in DMSO, water, PEG 400 (average molecular weight = 380-420), and PEG-DME (average molecular weight = 500).…”

“…78 The N(2)-Pt(1)-N(2) 0 (180°), N(1)-Pt(1)-N(1) 0 (180°), and N(1)-Pt-N(2), N(1)-Pt-N(2) 0 (87.7(2)°and 92.3(2)°) angles showed the expected values for a square planar coordination geometry around the Pt atom. 79,80 In the cyclopropylamine ligands, the Pt-N distance (2. 84 Solution Behavior. To improve the solubility, 85 the biological activity of the amidine complexes 1-3 was investigated by dissolving them in DMSO, water, PEG 400 (average molecular weight = 380-420), and PEG-DME (average molecular weight = 500).…”

Coordination Aspects in Modern Inorganic Chemistry

“…Reactions of coordinated inorganic and organic ligands are of the high interest. In particular, in 1998-2007 reactivity of such ligands as nitriles (RCN) and oximes, coordinated to the ion Pt(IV) is intensively studied [50][51][52][53][54][55][56][57][58][59][60][61][62]. The main attention in these studies is given to the reactions of nucleophylic addition of various nucleophiles on the carbon atom of triple CN-bond of the nitrile fragment, whose electrophylic activation was reached because of its coordination to Pt(IV) 96.…”