- Structural and in vitro biological studies of organotin(iv) precursors; Selective inhibitory activity against human breast cancer cells, positive to estrogen receptors
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Crystals of Ph3SnCl (1) were grown from a methanol/acetonitrile solution. Compounds [Ph3SnOH]n (2) and [(Ph 2Sn)4Cl2O2(OH)2] (3) were crystallized from diethyl ether/methanol/acetonitrile and hot acetone/water solutions respectively, of the white precipitation, formed by adding KOH to solutions of 1 and [Ph2SnCl2] in 1:1 and 1:2 molar ratios respectively. Complex 1 was characterized by X-ray crystallography. X-ray structure determination of compounds 2 and 3 confirmed the previously reported identities. The molecular structure of 1, reported here, is a new polymorphic form of the known one for Ph3SnCl. Four independent [Ph 3SnCl] molecules constitute the crystal structure of 1. The moieties are packed in two pairs in a tail-to-tail arrangement. Complexes 1-3 were evaluated for their in vitro cytotoxic activity (cell viability) against human cancer cell lines: HeLa (human cervical), MCF-7 (breast, estrogen receptor (ER) positive), MDA-MB-231 (breast, ER negative), A549 (lung), Caki-1 (kidney carcinoma), 786-O (renal adenocarcinoma), K1 (thyroid carcinoma), and the normal human lung cell line MRC-5 (normal human fetal lung fibroblast cells) versus, the normal immortalized human mammary gland epithelial cell line MTSV17 with a sulforhodamine B (SRB) assay. The results show potent cytotoxic activity of the complexes against all cell lines used, which was superior to that of cisplatin (CDDP). Compounds 1-3 showed higher activity against breast cancer cells MCF-7 (ER positive) than against of MDA-MB-231 (ER negative). These findings prompted us to search for possible interaction of these complexes with other cellular elements of fundamental importance in cell proliferation. The influence of these complexes 1-3 upon the catalytic peroxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase (LOX), as well as their binding affinity towards calf thymus-DNA, were kinetically and theoretically studied.
- Balas, Vasilis I.,Banti, Christina N.,Kourkoumelis, Nikolaos,Hadjikakou, Sotiris K.,Geromichalos, George D.,Sahpazidou, Despina,Male, Louise,Hursthouse, Mike B.,Bednarz, Barbara,Kubicki, MacIej,Charalabopoulos, Konstantinos,Hadjiliadis, Nick
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- catena-poly[[triphenyltin(IV)]-μ-hydroxo-κ2O:O] at 120 K
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The structure of the title compound, [Sn(C6H5)3(OH)]n, has been re-investigated at 120 (2) K. The hydroxyl H atom was readily located and the threefold coordination about the O atom is planar. There are no hydro
- Glidewell, Christopher,Low, John N.,Bomfim, Joao A. S.,Filgueiras, Carlos A. L.,Wardell, James L.
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- Synthesis, structural characterization, Hirshfeld surface analysis and in vitro-antimicrobial activities of triphenyltin (IV) compounds of azo-carboxylates derived from 2- or 4-amino benzoic acids and naphthalen-1 or 2-ol
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Synthesis of three new triphenyltin(IV) compounds 1–3 were reported by the reaction of azo-carboxylic acid ligands viz.2/4-(2-hydroxynaphthylazo)-benzoic acids [compounds 1 and 2] or 2-(4-hydroxynaphthylazo)-benzoic acid [compound 3] with triphenyltin(IV)
- Debnath, Paresh,Debnath, Pratima,Maniukiewicz, Waldemar,Sharma, Swastika,Sieroń, Les?aw,Singh, Keisham Surjit,Singh, S. Sureshkumar
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- Antibacterial activity of diphenyltin(IV) and triphenyltin(IV) 3-chlorobenzoate againts Pseudomonas aeruginosa and Bacillus subtilis
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In this paper, we reported the syntheses and antibacterial activity test of 2 organotin(IV) compounds, diphenyltin (IV) di-3-chlorobenzoate (2) and triphenyltin (IV) 3-chlorobenzoate (4). These two compounds were prepared by the reaction of diphenyltin (IV) dihydroxide and triphenyltin (IV) hydroxide with 3-chlorobenzoic acid. These compounds were characterized by 1H and 13C NMR, IR, UV-Vis spectroscopies and also based on the microanalytical data. The results of antibacterial activity by diffusion method against Pseudomonas aeruginosa and Bacillus subtilis showed that the triphenyltin(IV) 3-chlorobenzoate was active at concentration of 3.956 x 10-4M (200 ppm), while the chloramphenicol gave inhibition of 6.1894 x 10-4 M (200 ppm), although the halozone was bigger. This result indicated that compound 4 is potentially to be used as antibacterial substance, although the search of other derivative of organotin (IV) with other ligands is still needed to get much higher and much better activity.
- Annissa,Suhartati, Tati,Yandri,Hadi, Sutopo
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p. 1133 - 1139
(2017/08/01)
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- The synthesis, characterization and comparative anticorrosion study of some organotin(IV) 4-chlorobenzoates
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The synthesis of 3 compounds of a series of dibutyl(IV) di-4-chlorobenzoate, diphenyl(IV) di-4-chlorobenzoate and triphenyltin(IV) 4-chlorobenzoate have successfully been performed by reacting the dibutyltin(IV) dichloride, diphenyltin(IV) dichloride and triphenyltin(IV) chloride respectively via the dibutyltin(IV) oxide, diphenyltin(IV) dihydroxide and triphenyltin(IV) hydroxide with 4-chlorobenzoic acid. All compounds synthesized were well characterized by 1H and 13C NMR, IR and UV-Vis spectroscopies as well as based on the microanalytical data. The anticorrosion activity of these compounds were tested on Hot Roller Plate (HRP) mild steel in DMSO-HCl solution using potentiodynamic method. The results revealed that the triphenyltin(IV) 4-chlorobenzoate clearly showed the strongest inhibitor activity compared to the other derivatives, while diphenyltin(IV) compounds were better than that of dibutyltin(IV) analogous. The results reported here indicated that the optimal activity were depended on the ligand attached to the metal centre and might also be related to the number of carbon atoms present in the organotin(IV) used.
- Kurniasih, Hastin,Nurissalam, Muhamad,Iswantoro, Bambang,Afriyani, Hapin,Qudus, Hardoko Insan,Hadi, Sutopo
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p. 2377 - 2383
(2016/02/27)
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- Synthesis and properties of Ph3Sn substituted tellurates - The crystal structures of trans-[(Ph3SnO)4Te(OH)2] and trans-[(Ph3SnO)2Te(OMe)4]
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The reaction of Te(OH)6 with Ph3SnOH in ethanol leads to the formation of trans-[(Ph3SnO)4Te(OH)2] (1). Compound 1 crystallizes triclinic in the space group P1 with a = 996.6(2) pm, b = 1365.4(3) pm, c = 1368.2(3) pm and α = 71.15(2)°, β = 71.48(2)°, γ = 74.81(3)° (at 220 K). The molecular structure of 1 consists of a tellurium atom, which is coordinated nearly octahedrally by four Ph3SnO units and two hydroxyl groups that are trans to each other. The Te-O bond lengths are in the range of 190.5(2) and 193.7(2) pm. Treatment of 1 with methanol under reflux yields trans-[(Ph3SnO) 2Te(OMe)4] (2). Compound 2 crystallizes triclinic in the space group P1 with a = 1012.8(1) pm, b = 1422.4(2) pm, c = 1618.1(2) pm, and α = 100.44(1)°, β = 107.92(1)°, γ = 110.66(1)° (at 220 K). 2 forms centrosymmetric molecules in which the tellurium atom is surrounded nearly octahedrally by four methoxy groups and two trans arranged Ph3SnO units. The Te-O bond lengths of 187.9(3)-194.5(3) pm are similar to those observed in 1.
- Heratrich, Tobias,Merzweiler, Kurt
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p. 803 - 807
(2010/09/04)
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- Thermal epimerization of diastereomeric Grignard reagents
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Thermal epimerization is the key to changing the endo-to-exo ratio of the diastereomeric bornyl and fenchyl Grignard reagents from 67: 33 to 96: 4 and from 20: 80 to 80: 20, respectively.
- Beckmann, Jens,Schuetrumpf, Alexandra
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- MULTICOMPARTMENT GRANULATE FORMULATIONS FOR ACTIVE SUBSTANCES
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The invention relates to molded article that contains active substances and comprises at least two compartments that have a different material composition. Each compartment is independently provided with at least one active substance that is contained in a matrix. Each matrix encompasses at least one filler at a concentration of ≧20 percent by weight to ≦100 percent by weight relative to the total weight of the respective matrix. The invention further relates to a method for producing such molded articles as well as the use thereof.
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- Hydrolysis of dimethylphenyltin(IV) and triphenyltin(IV) chlorides in different aqueous ethanol solutions
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The hydrolysis of [(Me)2(Ph)Sn(IV)]+ and [(Ph) 3Sn(IV)]+ has been investigated at 25 °C and different aqueous solutions of ethanol, using a combination of spectrophotometric and potentiometric techniques. The species formed together with their formation constants have been determined using the computer program Squad over a wide pH range of 1 to 11. The hydrolysis constants in different media were analyzed in terms of Kamlet and Taft parameters. Single-parameter correlation of the formation constants, K11 and K12, versus α (hydrogen-bond donor acidity), β (hydrogenbond acceptor basicity), and π* (dipolarity/polarizability) for both cases are relatively poor in all solutions, but multiparameter correlation represents significant improvement with regard to the single-parameter models. In this work, we have also used the normalized polarity parameter, ETN, alone and in combination with the Kamlet-Taft parameter to find a better correlation of the formation constants in different aqueous ethanol solutions.
- Jabbari, Morteza,Gharib, Farrokh,Amini, Mostafa Mohammadpour,Azadmehr, Amirreza
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p. 751 - 756
(2008/12/20)
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- Structural investigations on diorgano- and triorganotin(IV) derivatives of [meso-tetra(4-sulfonatophenyl)porphine] metal chlorides
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Several new complexes of organotin(IV) moieties with MCl n[meso-tetra(4-sulfonatophenyl)porphine], (R2Sn) 2MCln[meso-tetra(4-sulfonatophenyl)-porphinate]s and (R3Sn)4MCln [meso-tetra(4-sulfonatophenyl) porphinate]s, [M = Fe(III), Mn(III): n = 1, R = Me, n-Bu; Ph; M = Sn(IV): n = 2, R = Me, n-Bu] have been synthesized and their solid state configuration investigated by infrared (IR) and M?ssbauer spectroscopy, and by 1H and 13C NMR in D2O. The electron density on the metal ion coordinated inside the porphyrin ring is not influenced by the organotin(IV) moieties bonded to the oxygen atoms of the side chain sulfonatophenyl groups, as it has been inferred on the basis of M?ssbauer spectroscopy and, in particular, from the invariance of the isomer shift of the Fe(III) and Sn(IV) atoms coordinated into the porphyrin square plane of the newly synthesized complexes, with respect to the same atoms in the free ligand. As far as the coordination polyhedra around the peripheral tin atoms are concerned, infrared spectra and experimental M?ssbauer data would suggest octahedral and trigonal bipyramidal environments around tin, in polymeric configurations obtained, respectively, in the diorganotin derivatives through chelating or bridging sulfonate groups coordinating in the square plane, and in triorganotin(IV) complexes through bridging sulfonate oxygen atoms in axial positions. The structures of the (Me3Sn)4Sn(IV)Cl 2[meso-tetra(4-sulfonatophenyl)porphinate] and of the two model systems, Me3Sn(PS)(HPS) and Me2Sn(PS)2 [HPS = phenylsulfonic acid], have been studied by a two layer ONIOM method, using the hybrid DFT B3LYP functional for the higher layer, including the significant tin environment. This approach allowed us to support the structural hypotheses inferred by the IR and M?ssbauer spectroscopy analysis and to obtain detailed geometrical information of the tin environment in the compounds investigated. 1H and 13C NMR data suggested retention of the geometry around the tin(IV) atom in D2O solution.
- Pellerito,Scopelliti,Fiore,Nagy,Barone,Abbate,Stocco,Pellerito
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p. 1573 - 1583
(2007/10/03)
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- Synthesis, characterisation and reactivity of 2-functionalised vinylstannanes
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The functionalised vinylstannanes of the type (E)/(Z)-Ph3SnCR′=CHYRn and (E)/(Z)-Ph3SnC(YRn)=CHR′ (YRn=NMe2, OEt, SMe, SEt; R′=Ph, Bu (n-butyl), Pe (n-pentyl), H) were prepared by non-catal
- Lébl,Hole?ek,Dymák,Steinborn
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- Reactions of organolanthanide compounds RLnI (Ln = Yb, Eu, Sm) with organic derivatives of silicon, tin, lead, and antimony
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Reactions of compounds RLnI (R = Alk, Ar; Ln = Yb, Eu, Sm) with hexaalkyl(aryl)-distannanes, trimethylsilyltriphenyltin, and lead and antimony acetates were studied. The reactions with Sn-Sn and Si-Sn organic derivatives result in cleavage of Sn-Sn amd Sn-Si bonds with formation of tetrasubstituted stannanes and reactive organometallic derivatives with an Sn-Ln or Si-Ln bond. The reactions of RYbI with lead and antimony acetates and with tetraethoxysilane cause cleavage of the Pb-O, Sb-O, or Si-O bond with formation of tetrasubstituted derivatives of lead and silicon or trisubstituted antimony derivatives.
- Rybakova,Syutkina,Petrov
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p. 244 - 246
(2007/10/03)
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- Cleavage of Sn-Sn Bonds in Hexaalkyl(aryl)stannanes under the Action of Yb(II) Derivatives
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Ytterbium(II) derivatives MeYbI, PhYbI, and YbI2 cleave the Sn-Sn bond in distannanes R′3-SnR′3 (R′ = n-Bu, Ph) to give heterobimetallic derivatives R′3SnYbI, which were identified by products of their hydrolysis, exchange with R″3EHlg (R″ = Ph, Me; E = Ge, Si, Sn) and cross coupling with MeI in the presence of NiCl2(Ph3P)2.
- Syutkina,Rybakova,Novgorodova,Petrov
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- Coupurs par transfert d'electrons de la liaison Sn-CH2 dans les composes R3SnCH2X
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In the presence of nucleophiles , the Sn-CH2 bond in organotin iodides R3SnCH2I with R=Me, Et and Ph is cleaved by an ionic mechanism or by an electron-transfer involving R3SnCh2., R3SnCH2CN(1). and R3Sn. radicals which can be induced electrochemically.Dimerisation, reoxydation of reduction of the R3Sn. radical occur depending on the potential, the solvent and the substituent.A complete description of the mechanism led us to study the electrochemical behaviour of R3SnCH2I iodides and resulted in a simple preparation of bis mercury compounds.
- Devaud, Marguerite,Lecat, Jean-Luc
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p. 1187 - 1190
(2007/10/02)
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