Synthesis of potential platinum(II) anti-tumor complexes: Complexes containing bidentate pyridyl and imidazolyl donors

Canty, Allan J.; Stevens, Elizabeth A.

doi:10.1016/s0020-1693(00)90768-0

Cited by 26 publications

(3 citation statements)

References 15 publications

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“…In the former case, salt complexes of general formula [M(LH) n ] m + are obtained, whereas the latter should lead to neutral chelates of the type ML n . The few known examples concerning the coordinating properties of simple bisheteroarylmethanes are basically limited to bis(quinol-2-yl)methane and bis(pyrid-2-yl)methane . However, with very few exceptions, in none of these studies were neutral chelates ML n reported.…”

Section: Introductionmentioning

confidence: 99%

Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands¹

et al. 2002

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We describe the synthesis of a number of 1,3-azol-2-yl-, 1,3-benzazol-2-yl-, and azinyl-based bis(o-azaheteroaryl)methanes (LH, L(-) = Het(2)CH(-)) and their coordinating properties toward divalent transition metals (Zn, Cu, Co, Ni, Hg, Pd). This extended investigation includes both symmetrical and unsymmetrical ligands based on several substituted and/or unsubstituted thiazole, benzothiazole, benzoxazole, benzimidazole, pyridine, and quinoline derivatives. Depending on the structure and electron properties of the ligand, a vast set of neutral chelates ML(2) were obtained, where the ligand is present in its carbanionic form L(-). Additionally, we have prepared salt complexes [M(LH)(n)]X(m), where the ligand is present as a neutral system. Neutral chelates were typically obtained by the reaction of the ligand with metal acetates in alcoholic solution; salt complexes were formed by reaction with other metal salts such as chlorides. By exploring the coordinating properties of several bisheteroarylmethane ligands based on heteroaromatics of variable pi-electron structure and substitution pattern, we demonstrate that the formation of neutral chelates is strictly dependent on the electron-withdrawing capacity (charge demand) of the heteroaromatic moiety. The latter primarily dictates the efficiency by which the negative charge of the anionic ligand L(-) is stabilized by delocalization in ML(2) and, therefore, the stability of the chelate itself. On the basis of the large number and the variable nature of the nitrogen ligands used, we confirm the general validity of the charge-demand-dependent formation of chelates. This key factor can therefore be used for the efficient design of new pi-deficient heteroaromatic nitrogen ligands in chelates of great potential in many synthetic, catalytic, and technological fields.

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Section: Introductionmentioning

confidence: 99%

Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands¹

et al. 2002

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“…( SP ‐4‐2)‐Dichlorido[2,2′‐(methane‐1,1‐diyl)dipyridine]platinum(II) (L 1 PtCl 2 ): The complex was synthesised as described previously, with slight modifications . L 1 (41 mg, 0.24 mmol) in MeOH (1 mL) was added to a solution of K 2 [PtCl 4 ] (100 mg, 0.24 mmol) in H 2 O (3 mL).…”

Section: Methodsmentioning

confidence: 99%

“…The complex was synthesised as described previously, with slight modifications. [31] L 1 (41 mg, 0.24 mmol) in MeOH (1 mL) was added to a solution of K 2 [PtCl 4 ] (100 mg, 0.24 mmol) in H 2 O (3 mL). The mixture was stirred overnight in a light-protected flask.…”

Section: (Sp-4-2)-dichlorido[22′-(methane -11-diyl)dipyridine]platinu...mentioning

confidence: 99%

Antiproliferative Copper(II) and Platinum(II) Complexes with Bidentate N,N‐Donor Ligands

et al. 2017

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Three copper(II) complexes of a series of bidentate dipyridylmethane ligands, as well as their structurally related platinum(II) analogues, have been synthesised and fully characterised to evaluate their coordination chemistry and antiproliferative properties. New crystal structures of the complexes L3CuCl2, L2PtCl2 and L3PtCl2, where L2, L3 have one and two methyl substituents on the bridgehead carbon atom between the coordinated pyridine ligands, respectively, were obtained. The in vitro cytotoxicity of the free ligands and their corresponding platinum and copper complexes was evaluated in the cisplatin‐sensitive ovarian teratocarcinoma cell line CH1/PA1, as well as in rather cisplatin‐insensitive colon (SW480) and lung (A549) carcinoma cells, using the MTT assay. All six complexes showed higher cytotoxicity than the ligands L1–L3 alone, giving IC50 values in the low micromolar range.

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ChemInform Abstract: SYNTHESIS OF POTENTIAL PLATINUM(II) ANTITUMOR COMPLEXES: COMPLEXES CONTAINING BIDENTATE PYRIDYL AND IMIDAZOLYL DONORS

Canty¹,

Stevens²

1981

Chemischer Informationsdienst

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Synthesis of potential platinum(II) anti-tumor complexes: Complexes containing bidentate pyridyl and imidazolyl donors

Cited by 26 publications

References 15 publications

Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands¹

Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands¹

Antiproliferative Copper(II) and Platinum(II) Complexes with Bidentate N,N‐Donor Ligands

ChemInform Abstract: SYNTHESIS OF POTENTIAL PLATINUM(II) ANTITUMOR COMPLEXES: COMPLEXES CONTAINING BIDENTATE PYRIDYL AND IMIDAZOLYL DONORS

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Synthesis of potential platinum(II) anti-tumor complexes: Complexes containing bidentate pyridyl and imidazolyl donors

Cited by 26 publications

References 15 publications

Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands1

Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands1

Antiproliferative Copper(II) and Platinum(II) Complexes with Bidentate N,N‐Donor Ligands

ChemInform Abstract: SYNTHESIS OF POTENTIAL PLATINUM(II) ANTITUMOR COMPLEXES: COMPLEXES CONTAINING BIDENTATE PYRIDYL AND IMIDAZOLYL DONORS

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Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands¹

Metal Chelation Aptitudes of Bis(o-azaheteroaryl)methanes As Tuned by Heterocycle Charge Demands¹