Novel carboplatin analogs containing flexible and potentially intercalating ligands: preparation and X-ray crystal structures of di-2-pyridyl ketone cyclobutanedicarboxylate platinum(II) and of 2,3-bis(2-pyridyl)pyrazine cyclobutane dicarboxylate platinum(II)

Ferreira, Alba D.Q.; Bino, Avi; Gibson, Dan

doi:10.1016/s0020-1693(97)05742-3

Cited by 29 publications

(19 citation statements)

References 23 publications

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“…The 195 Pt NMR spectrum of complex 11 showed a single peak at -1950 ppm, which belongs to the 195 Pt chemical shift range of other Pt(biamine)(CBDCA) (biamine = bidentate diamine) complexes. 20,33,34 Even though the carboplatin analogs 9, 10 and 11 showed slightly increased aqueous solubility in comparison to that of the corresponding cisplatin analogs 7 and 8, as expected, all three compounds still showed good solubility in most organic solvents such as methylene chloride, acetone, and THF. Interestingly, Pt(5)(CBDCA) (10) containing 4,4¢-substituted 2,2-bipyridine, was found to be very stable in DMSO solvent, while complexes 9 and 11, which contain 3,3¢-substituted 2,2-bipyridine, exhibited a rapid solvolysis reaction in DMSO, leading to the replacement of one of the coordinated imines of the bidentate bipyridine rings with one DMSO solvent molecule.…”

Section: Methodssupporting

confidence: 66%

Synthesis of stable platinum complexes containing carborane in a carrier group for potential BNCT agents

Yoo

2009

Dalton Trans.

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A series of stable platinum complexes containing closo-carborane cages in a 'carrier group', which could be potentially utilized for boron neutron capture therapy (BNCT), was successfully synthesized and characterized by various spectroscopic methods. Two ortho-closo-carborane cages were connected to the 3,3' or 4,4'-positions of 2,2'-bipyridine through ester bonds to give three carborane-linked bipyridine ligands, 3,3'-(3-(1,2-dicarba-closo-dodecaborane-1-yl)propoxycarbonyl)-2,2'-bipyridine (3) and n,n-(3-(1-methyl-1,2-dicarba-closo-dodecaborane-1-yl)propoxycarbonyl)-2,2-bipyridine (n = 3 4; n = 4 5). The prepared ligands successfully replaced the labile benzonitrile groups of [Pt(PhCN)2Cl2] to afford three cisplatin analogs [Pt(L)Cl2] (L = 3-5). In order to increase their aqueous solubility, three carboplatin analogs, [Pt(L)(CBDCA), L = 4 and 5, CBDCA = 1,1-cyclobutanedicarboxylate] and [Pt( 4)(oxalate)], were synthesized by employing [Pt(DMSO)2(CBDCA)] or [Pt(DMSO)2(oxalate)] as a starting platinum(II) source. Two platinum(IV) complexes [Pt(L)Cl4, L = 4 and 5] were also successfully prepared from Na2[PtCl6] x 6H2O. All of the synthesized platinum complexes containing closo-carboranes exhibited excellent stability in both the solid and solution states and could be stored in air for several months. Even though the three closo-carborane ligands were successfully deboronated to the corresponding nido-mono anions by employing a mild degradation method involving CsF/ethanol, all attempts at the incorporation of nido-carborane-linked bipyridine into the platinum complexes failed, leading to the formation of black precipitates of reduced platinum.

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Section: Methodssupporting

confidence: 66%

Synthesis of stable platinum complexes containing carborane in a carrier group for potential BNCT agents

Yoo

2009

Dalton Trans.

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“…It confirms the presence of an octahedral platinum(IV) centre with chelating cyclobutane malonate group, as expected for the product of cis oxidative addition. This PtO 2 C 3 six-membered chelate ring adopts a twist boat conformation, similar to that observed in other platinum cyclobutane malonate complexes, [49][50][51][52][53] with the cyclobutane carbon atom C(22) oriented away from the bubpy group. The bond distances trans to the methyl groups are long, so that Pt(1)−O(1) is longer than Pt(1)−O(4) and Pt(1)−N(2) is longer than Pt(1)−N(1) (Fig.…”

Section: Oxidative Addition Reactions and Product Characterizationsupporting

confidence: 77%

Oxidation of dimethylplatinum(II) complexes with malonyl peroxide derivatives

et al. 2015

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The reaction of the cyclic peroxides cyclobutane malonoyl peroxide and cyclopentane malonoyl peroxide to dimethylplatinum(II) complexes with the bidentate nitrogen donor ligand 4,4=-di-t-butyl-2,2=-bipyridine (bubpy) gave a mixture of the products of cis and trans oxidative addition, [PtMe 2 {(O 2 C) 2 C(C 3 H 6 )}(bubpy)] and [PtMe 2 {(O 2 C) 2 C(C 4 H 8 )}(bubpy)], respectively. The cis isomers exist with a chelating dicarboxylate ligand, forming a six-membered ring, while the trans isomers are thought to exist as oligomers, which may react with water or solvent to give complexes containing a monodentate dicarboxylate ligand. Equilibration of the product of cis oxidative addition, cis-[PtMe 2 {(O 2 C) 2 C(C 3 H 6 )}(bubpy)], with oxalic or phthalic acid to give equilibria with the oxalate cis-[PtMe 2 (O 4 C 2 )(bubpy)] or phthalate cis-[PtMe 2 {(O 2 C) 2 C 6 H 4 }(bubpy)] derivative, respectively, indicated the expected sequence of chelate stability oxalate > cyclobutane malonate > phthalate. Résumé: La réaction de peroxydes cycliques, le peroxyde de cyclobutane malonoyle et le peroxyde de cyclopentane malonoyle, avec des complexes de diméthylplatine (II) en présence du 4,4=-di-t-butyl-2,2=-bipyridine (bubpy), ligand bidentate donneur d'azote, a formé un mélange de produits d'addition oxydante cis et trans, le [PtMe 2 {(O 2 C) 2 C(C 3 H 6 )}(bubpy)] et le [PtMe 2 {(O 2 C) 2 C(C 4 H 8 )}(bubpy)], respectivement. Les complexes avec un ligand dicarboxylate chélatant existent sous forme d'isomères cis et forment un cycle à six atomes, tandis qu'on croit que les isomères trans existent sous forme d'oligomères qui peuvent réagir avec l'eau ou un solvant pour produire des complexes comprenant un ligand dicarboxylate monodentate. L'équilibration du produit d'addition oxydante cis, le cis-[PtMe 2 {(O 2 C) 2 C(C 3 H 6 )}(bubpy)], avec l'acide oxalique ou phtalique qui se produit pour former respectivement à l'état d'équilibre les dérivés cis-[PtMe 2 (O 4 C 2 )(bubpy)] oxalate ou cis-[PtMe 2 {(O 2 C) 2 C 6 H 4 }(bubpy)] phtalate, révèle la séquence de stabilité attendue des chélates : oxalate > malonate de cyclobutane > phthalate. [Traduit par la Rédaction]

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“…The search for novel metallo-supramolecular materials has also directed much attention towards ligands containing two non-equivalent metal binding units. For example, the ligand dipyridylketone (dpk), has been studied extensively [21][22][23][24][25][26][27][28][29][30][31][32][33][34][35] and has been shown to readily hydrate upon co-ordination to give (2-py) 2 C(OH) 2 , (2-py) 2 C(OR)(OH), (2py) 2 C(OH)O -, (2-py) 2 C(OR)O -, and (2-py) 2 CO 2 2-(Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

The co-ordination chemistry of bis(2,2′-bipyrid-6′-yl)ketone with first row transition metals: The reversible interconversion of a mononuclear complex and a dinuclear hemiketal containing species

et al. 2010

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Bis(2,2'-bipyrid-6'-yl)ketone has been shown to co-ordinate to Zn(II) to form either a dinuclear hemiketal complex in methanol solutions or mononuclear complexes in acetonitrile. The ligand readily complexes to the late transition metals in acetonitrile to yield mononuclear complexes (Mn(II), Co(II), Ni(II),Zn(II) and Cd(II)) however for Fe(II) only dinuclear complexes [Fe(2){(2-bipy)(2)C(OMe)O(-)}(2)][ClO(4)](2) could be isolated. The solid state structures of the mononuclear complexes exhibit varying degrees of distortion compared to an anticipated planar array of bipyridyl donors.

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Novel carboplatin analogs containing flexible and potentially intercalating ligands: preparation and X-ray crystal structures of di-2-pyridyl ketone cyclobutanedicarboxylate platinum(II) and of 2,3-bis(2-pyridyl)pyrazine cyclobutane dicarboxylate platinum(II)

Cited by 29 publications

References 23 publications

Synthesis of stable platinum complexes containing carborane in a carrier group for potential BNCT agents

Synthesis of stable platinum complexes containing carborane in a carrier group for potential BNCT agents

Oxidation of dimethylplatinum(II) complexes with malonyl peroxide derivatives

The co-ordination chemistry of bis(2,2′-bipyrid-6′-yl)ketone with first row transition metals: The reversible interconversion of a mononuclear complex and a dinuclear hemiketal containing species

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