Synthesis, characterization and cytotoxic activity of complexes of diorganotin(IV) dihalides with mepirizole (original) (raw)
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Complexes of tin(IV) halides and diorganotin(IV) dihalides with 3,5-dimethyl-1-(2′-pyridyl)pyrazole
Inorganica Chimica Acta, 2003
3,5-Dimethyl-1-(2?-pyridyl)pyrazole (DMPP) reacts with SnX 4 and R 2 SnX 2 (X Ä/Cl, Br, I; R 0/Me, Et, Bu, Ph) to yield adducts of types [SnX 4 (DMPP)] and [SnR 2 X 2 (DMPP)], respectively. The structure of [SnEt 2 Br 2 (DMPP)] has been determined by X-ray diffractometry. The crystal consists of discrete [SnEt 2 Br 2 (DMPP)] molecules with the metal atom octahedrally coordinated to two Br atoms [SnÃ/Br0/2.631 , 2.703(3) Å ; BrÃ/Sn Ã/Br0/98.00(10)8], two ethyl carbons [SnÃ/C0/2.11(3), 2.143(19) Å ; CÃ/SnÃ/C0/ 172.3(11)8] and the two donor N atoms of the ligand [SnÃ/N 0/2.379(16), 2.387(16) Å ; NÃ/SnÃ/N 0/66.8(6)8]. The IR data and Mö ssbauer parameters are consistent with all the organotin derivatives having, similar geometry whereas in the case of the [SnX 4 (DMPP)] complexes the results of both techniques support the expectation of cis stereochemistry. The 1 H NMR data indicate significant dissociation in solution. The chlorobutyl derivative exhibited significant in vitro antitumour activity against the human carcinoma cell line KB. #
Applied Organometallic Chemistry, 1999
The compounds [SnR 2 X 2 (bmimt)] (R = Me, Et, Bu; X = Cl, Br; bmimt = bis(1-methyl-2-imidazolylthio)methane) have been prepared and characterized by conductivity measurements and by IR, Raman, mass, Mössbauer and 1 H NMR spectroscopy. The structures of the diethyldibromo-and dibutyldichlorotin(IV) derivatives were determined by X-ray crystallography. The crystals consist of two slightly different types of discrete [SnR 2 X 2 (bmimt)] unit with the metal atom octahedrally coordinated to the two halogen atoms, two alkyl carbons and the two nonmethylated nitrogen atoms of the ligand. This coordination mode, which the spectroscopic data suggest is also present in all the other complexes studied, results in the formation of an eight-membered CS 2 C 2 N 2 Sn ring. The Sn-N distances in [SnEt 2 Br 2 (bmimt)] (2.53 and 2.42 Å ) and [SnBu 2 Cl 2 (bmimt)] (2.52 and 2.47 Å ), suggest that these compounds may have antitumour activity.
Applied Organometallic Chemistry, 2005
-5methoxy-2-methyl-1H-indole-3-acetate (4) are described. These compounds have been characterized by 1 H, 13 C and 119 Sn NMR spectroscopy in solution and 119 Sn NMR in the solid state, infrared spectroscopy, elemental analysis and X-ray diffraction for compound 1. The growth inhibition effects of compounds 1-4 against the lung adenocarcinoma cell line SK-LU-1 as well as the cervical cancer cell line HeLa were determined. Compounds 1 and 2 exhibit cytotoxic activity, whereas compounds 3 and 4 are inactive.
Organotin(IV) complexes are well known for their diverse structural features and biological applications. The two tin compounds, Di(mbromobenzyl)(dibromo)tin(IV) (1) and di(m-chlorobenzyl)(dibromo)tin(IV) (2) when treated with 1, 10-phenanthroline yielded the complexes Di(m-bromobenzyl)(dibromo)(1,10-phenanthroline)tin(IV) (3) and Di(m-chlorobenzyl) (dibromo)(1,10-phenanthroline)tin(IV) (4). The molecular structure of these complexes are confirmed by spectroscopic (1 H, 13 C and 119 Sn NMR), XRD and DFT studies. The distorted octahedral geometries with axially disposed carbon atoms are confirmed and the new complexes show better anticancer activity when compared to that of cis-platin.
Journal of Organometallic Chemistry, 2006
The heterocyclic ligands [1,2,4]triazolo-[1,5-a]pyrimidine (tp) and 5,7-dimethyl-[1,2,4]triazolo-[1,5-a]pyrimidine (dmtp), react with diorganotin dichlorides giving the addition compounds Me 2 SnCl 2 (tp) 2 , Et 2 SnCl 2 (tp) 2 , Me 2 SnCl 2 (dmtp) 2 , Et 2 SnCl 2 (dmtp) 2 , Bu 2 SnCl 2 (dmtp), Ph 2 SnCl 2 (dmtp). The organotin:ligand stoichiometry goes from 1:2 to 1:1 by increasing the steric hindrance of the organic groups bound to tin. The compounds have been characterized by means of infrared, 119 Sn Mö ssbauer and 1 H AND 13 C NMR spectroscopy. The ligands presumably coordinate to tin classically through the nitrogen atom at the position 3. The 1:1 complexes adopt trigonal bipyramidal structures, with the organic groups on the equatorial plane and the ligand in the apical position. All-trans octahedral structures are inferred for the 1:2 complexes, except for Et 2 SnCl 2 (tp) 2 , characterized by a skew-trapezoidal structure. 119 Sn Mö ssbauer measurements, at room temperature, in concomitance with DFT calculations, performed on isomeric structures of R 2 SnCl 2 (tp) 2 (R = Me, Et), allowed us to conclude that the all-trans octahedral coordination induces self-assembly in the solid state, possibly accomplished through p-p stacking interactions among the planar ligands coordinated to the organotin(IV) compound, while the skew-trapezoidal structure attributed to Et 2 SnCl 2 (tp) 2 , induces the formation of monomeric adducts in the solid state. In vitro antimicrobial tests showed that [n-Bu 2 SnCl 2 (dmtp)] has interesting properties as anti Gram-positive and antibiofilm agent.
The synthesis and characterisation of diorganotin(IV) monomeric derivatives of pyridine Schiff bases and pyridinic carboxylic acids are reported. All complexes were characterised by mass spectrometry, elemental analyses, IR spectra, and multinuclear NMR analyses. Among them, complexes 5a, 5d, 5e, 5g, and 6a were also confirmed by X-ray crystallography diffraction analyses, which led to establishing that the tin atom is seven-coordinated and has a distorted pentagonal–bipyramidal coordination environment in the solid state and also revealed that both ligands occupy the equatorial positions and the organic substituents the axial positions. The antioxidant activity of the synthetic derivatives towards 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) as well as the thiobarbituric acid reactive substances (TBARS) assay were determined, and were compared with standard antioxidants, showing a dose-dependent activity in both cases. A prominent response was obtained depending on the substituent. The anti-inflammatory activity was also evaluated on a 12-O-tetradecanoylphorbol-13-acetate (TPA) model of induced acute inflammation. The results of the biological tests are discussed in terms of structural characteristics.
Journal of Inorganic Biochemistry, 1998
Novel di-and tri-organotin(1V) derivatives of amoxicillin (amoxicillin-= Amox-= 6-[D(-)-/?aminophydroxyphenylacetamido]penicillinate) have been prepared. The isolated compounds showed stoichiometries of the type R,SnCIAmox * 2H,O, R,SnCIAmoxNa. 2H20 and R,SnAmox,. 2H,O (R=Me, Bu, Ph). The infrared spectra suggest that Amox-, in both R,SnCIAmox * 2H20 and R2SnAmox,. 2H,O, behaves as a monoanionic bidentate ligand, coordinating the tin(1V) atom through the ester-type carboxylate, as well as through the lactamic carbonyl. In R,SnCIAmoxNa. 2H20, Amox-coordinates the organotin(1V) moieties through the lactamic carbonyl. In all of the compounds, water molecules are not involved in coordination, as inferred by thermogravimetric (TG) investigation. In both R,SnCIAmox. 2H20 and R,SnCIAmoxNa .2H,O, trigonal bipyramidal configurations are proposed in the solid state, on the basis of infrared (IR) and Mossbauer spectroscopy, while in R,SnAmox2. 2H20 the coordination geometry at tin could be a skew-trapezoidal bipyramid, with two chelating amoxicillin residues which act as bidentate ligands in the trapezoidal plane, and with the organic groups in axial positions. The C-S n-C angles calculated from the experimental Mossbauer quadrupole splitting predict a bent skeleton in all the R2SnAmox2 2H20 derivatives. 'H and ' ,C NMR measurements showed that both R,SnCIAmox * 2H20 and R,SnAmox,. 2H20 are stable in DMSO-d, solutions, maintaining their solid-state configuration, while R,SnCIAmoxNa. 2H20 dissociates. Coordination hypotheses have been checked through the correlation between the Mossbauer isomer shift (6) and the partial atomic charge on tin atoms (Qs.) performed, for all the new organo-Author to whom correspondence should be addressed. tin(1V) compounds, on the basis of an equalization procedure applied to idealized trigonal bipyramidal structures for R2SnCIAmox 2H20 and R,SnCIAmoxNa. 2H20 and octahedral trans-R, for R2SnAmox2. 2H20.
Journal of Organometallic Chemistry, 2007
The reaction of dimethyl-, diethyl-and dibutyltin(IV) oxide with 2,6-lutidine-a 2 ,3-diol (Lu) [2-(hydroxymethyl)-3-hydroxy-6-methylpyridine] in toluene/ethanol has been investigated. The compounds were isolated and characterized by IR, Raman and Mö ssbauer spectroscopy, EI and FAB mass spectrometry and 1 H and 119 Sn NMR spectroscopy. The structures of Lu and [SnMe 2 (H 2 O)(Lu-2H)] were determined by X-ray diffraction. The crystal of [SnMe 2 (H 2 O)(Lu-2H)] contains dimeric [SnMe 2 (H 2 O)(Lu-2H)] 2 units, in which the tin atom is coordinated to the O atoms of the two deprotonated hydroxymethyl groups and one deprotonated phenolic hydroxyl group. The distorted octahedral coordination polyhedron of each tin atom is completed by a water molecule and two methyl C atoms. The butyl derivative exhibited significant in vitro antitumor activity against the human carcinoma cell lines HeLa-229, A2780 and A2780cis, although minor than that of the pyridoxine derivative prepared previously.