Antitumor activity of platinum(II) and palladium(II) complexes with ethyl quinolylmethylphosphonates

Nakon otkrića antitumorske aktivnosti cisplatine i njezinih analoga, te njihove vrlo uspješne kliničke primjene u liječenju određenih tipova tumora, intenzivno se istražuju novi platinski kompleksi i kompleksi drugih metala s ciljem dobivanja citostatika s boljim antitumorskim djelovanjem i manje izraženim nuspojavama. Naša istraživanja u tom području usmjerena su na komplekse platine i paladija s derivatima aminofosfonskih kiselina. U ovom radu dan je pregled kompleksa platine(II) i paladija(II) s dietil i monoetil 2- i 8-kinolilmetilfosfonatima te rezultati testiranja njihove in vitro antitumorske aktivnosti prema KB stanicama karcinoma kože kod ljudi i L1210 stanicama leukemije kod miša. Nekoliko kompleksa pokazalo je visoku aktivnost. Razmatranje odnos antitumorske aktivnosti kompleksa o njihovim strukturnim i fizičko-kemijskih svojstvima.After the discovery of antitumor activity of cisplatin and its analogues, as well as their successful medical application in the treatment of a variety of tumors, there is a continuing interest in development of new platinum- or other metal-based drugs with improved antitumor activity and less pronounced side effects. Our specific interest in this field is focused on platinum and palladium complexes with derivatives of aminophosphonic acids. The purpose of this review is to describe the platinum (II) and palladium(II) complexes of diethyl and monoethyl 2- and 8-quinolylmethylphosphonates and the results obtained by evaluation for their ability to inhibit the cancer growth in vitro in the epidermoid human carcinoma (KB) and murine leukemia (L1210) cell lines. Some complexes have shown high cell growth inhibitory effects. Relation between the activity of complexes and their physico-chemical and structural properties has been discussed

Antitumor activity of platinum(II) and palladium(II) complexes with ethyl quinolylmethylphosphonates

Nakon otkrića antitumorske aktivnosti cisplatine i njezinih analoga, te njihove vrlo uspješne kliničke primjene u liječenju određenih tipova tumora, intenzivno se istražuju novi platinski kompleksi i kompleksi drugih metala s ciljem dobivanja citostatika s boljim antitumorskim djelovanjem i manje izraženim nuspojavama. Naša istraživanja u tom području usmjerena su na komplekse platine i paladija s derivatima aminofosfonskih kiselina. U ovom radu dan je pregled kompleksa platine(II) i paladija(II) s dietil i monoetil 2- i 8-kinolilmetilfosfonatima te rezultati testiranja njihove in vitro antitumorske aktivnosti prema KB stanicama karcinoma kože kod ljudi i L1210 stanicama leukemije kod miša. Nekoliko kompleksa pokazalo je visoku aktivnost. Razmatranje odnos antitumorske aktivnosti kompleksa o njihovim strukturnim i fizičko-kemijskih svojstvima.After the discovery of antitumor activity of cisplatin and its analogues, as well as their successful medical application in the treatment of a variety of tumors, there is a continuing interest in development of new platinum- or other metal-based drugs with improved antitumor activity and less pronounced side effects. Our specific interest in this field is focused on platinum and palladium complexes with derivatives of aminophosphonic acids. The purpose of this review is to describe the platinum (II) and palladium(II) complexes of diethyl and monoethyl 2- and 8-quinolylmethylphosphonates and the results obtained by evaluation for their ability to inhibit the cancer growth in vitro in the epidermoid human carcinoma (KB) and murine leukemia (L1210) cell lines. Some complexes have shown high cell growth inhibitory effects. Relation between the activity of complexes and their physico-chemical and structural properties has been discussed

Conductance Study of Ion-Pairing of Alkali Picrate and Tetraphenylborate Complexes with Some Macrocyclic Polyethers in Methanol

The conductance of dibenzo-18-cmwn-6 (DB18C6), bis (3,5-di-,tert-butylbenzo)-18-crown-6 (dtbDB18C6) and dibenzo- 24-crown-8 (DB24C8) complexes with sodium and potassium picrates and tetr-a;phenylborates was investigated in methanol at 25 •c. Shedlovsky plots gave straight lines from which the limiting conductances, .Ao, and ion-pai.r dissociation constants, Kv, were calculated. Generally, tetraphenylbora:te complexes are slightly more dissociated than the corrnsponding picrate complexes, as are also the potassium complexes compared to those of the sodium salts. The results obtained are compared with !those obtaillled for the conductance of sodium and po.tassium picrates and tetraphenylborates in methanol, and are discussed in terms of the polyether interactions with al•kali cation which are controlled by their size, solvent interactions with the polyether- cation complexes, size and charge density of the counterion, and the steric factors caused by the presence of the bulky tert-butyl substituents in the polyether molecule

Synthesis and characterization of metallocyclic complexes of palladium(II) with monoalkyl (alpha-anilino-N-benzyl)phosphonates

The synthesis, spectroscopic and thermal properties of the novel five-membered [N,O] metallocyclic complexes of palladium(II) with monoethyl (HL1) and monobutyl (HL2) esters of (alpha -amino-N-benzyl)phosphonic acid are reported. Binuclear complexes Pd(2)L(4) (L = L1, L2) were obtained by reaction of sodium salts of monoalkyl phosphonates with PdCl(4)(2-) in aqueous solution. Four organophosphorus ligands bridge two palladium atoms by coordination through the aniline nitrogen and the deprotonated phosphonic acid oxygen. The complexes were identified and characterized by elemental analysis, magnetic and conductance measurements, as well as by spectroscopic (ESI-MS, IR, UV-VIS, (1)H and (31)P NMR) and thermal (TG, DTA) studies. The properties of the complexes are discussed with respect to those of palladium(II) metallocyclic complexes reported for monoalkyl 4-azobenzene-substituted anilinobenzylphosphonates

Synthesis and Characterization of Metallocyclic Complexes of Palladium(II) with Monoalkyl (α-Anilino-N-benzyl)phosphonates

The synthesis, spectroscopic and thermal properties of the novel five-membered [N,O] metallocyclic complexes of palladium(II) with monoethyl (HL1) and monobutyl (HL2) esters of (α-anilino-N-benzyl)phosphonic acid are reported. Binuclear complexes Pd2L4 (L = L1, L2) were obtained by reaction of sodium salts of monoalkyl phosphonates with PdCl42- in aqueous solution. Four organophosphorus ligands bridge two palladium atoms by coordination through the aniline nitrogen and the deprotonated phosphonic acid oxygen. The complexes were identified and characterized by elemental analysis, magnetic and conductance measurements, as well as by spectroscopic (ESI-MS, IR, UV-VIS, 1H and 31P NMR) and thermal (TG, DTA) studies. The properties of the complexes are discussed with respect to those of palladium(II) metallocyclic complexes reported for monoalkyl 4-azobenzene-substituted anilinobenzylphos-phonates

Synthesis and Crystal and Molecular Structure of trans-[PtCl2(8-dqmp)2]* (8-dqmp = diethyl 8-quinolylmethylphosphonate)

The complex trans-PtCl2(8-dqmp)2 – trans-dichloro-bis(diethyl 8-quinolylmethylphosphonate-κN)platinum(II) – has been synthesized and the molecular structure has been determined by a rystallographic study. The platinum atom has a slightly distorted trans square-planar configuration with Pt1–N1 = 2.042(4) and Pt1–Cl1 = 2.306(1) Å. The dihedral angle between the Pt coordination plane and the mean plane of the 8-quinolylmethyl moiety is 65.1(1)°. The complex reveals a very interesting feature: a very short methylene proton–platinum distance of 2.309(5) Å occupying approximately axial positions around the central metal atom for the hydrogen atom H10B. Refinement was performed by least-squares methods to a final R value of 3.02%

The Synthesis and Crystal Structures of 7-Bromo-1,3-dihydro-1-methyl-3(S)-methyl-5-(2\u27-pyridyl)-2H-1,4-benzodiazepin-2-one and Its CuII Complex

By reaction of the enantiomerically pure 7-bromo-1,3-dihydro-1-methyl-3(S)-methyl-5-(2\u27-pyridyl)-2H-1,4-benzodiazepin-2-one, (+)-1, with CuCl2 ∙ 2H2O in a mixture of absolute ethanol and dichloromethane, dichloro-[7-bromo-1,3-dihydro-1,3-dimethyl-5-(2\u27-pyridyl)-2H-1,4-benzodiazepin-2-on-N,N,O]copper(II), (±)-2, was obtained. In both structures, the characteristic boat conformation of the seven-membered benzodiazepine ring was observed. Complex 2, which was isolated as a racemic compound, revealed a slightly distorted trigonal bipyramid. Copper(II) was coordinated by two azometine nitrogen atoms, two chlorine atoms and the lactam oxygen of a neighbouring molecule. In this way, an infinite chain of complex molecules was formed in the crystal. The chemical behaviour of ligand 1 upon CuII coordination was compared with its 3-hydroxymethyl and 3-acetoxymethyl analogues