- Diversity of complexes based on p-nitrobenzoylhydrazide, benzoylformic acid and diorganotin halides or oxides self-assemble: Cytotoxicity, the induction of apoptosis in cancer cells and DNA-binding properties
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Eight organotin(IV) complexes (C1-C8) have been synthesized and characterized by elemental analysis, fourier transform infrared spectroscopy (FT-IR), multinuclear nuclear magnetic resonance (1H, 13C and 119Sn NMR), high resolution mass spectroscopy (HRMS) and single crystal X-ray structural analysis. Crystallographic data show that C1 was a tetranuclear 16-membered macrocycle complex, C2-C4 and C7 were centrosymmetric dimer distannoxane and there was a Sn2O2 four-membered ring in the middle of the molecule, respectively, C5 and C6 are monoorganotin complexes due to the dehydroalkylation effect during the reaction, while C8 forms a one-dimensional chain structure. The cytotoxicity of all complexes were tested by 3-(4,5)-dimethylthiahiazo(-z-y1)-3,5-di-phenytetrazoliumromide (MTT) assays against three human tumor cell lines NCI-H460, MCF-7 and HepG2. The dibutyltin complex C2 has been shown to be more potent antitumor agents than other complexes and carboplatin. Cell apoptosis study of C2 with the high activity on HepG2 and MCF-7 cancer cell lines was investigated by flow cytometry, it was shown that the antitumor activity of C2 was related to apoptosis, but it has different cell cycle arrest characteristics from platinum compounds, and the proliferation was inhibited by blocking cells in S phase. The DNA binding activity of the C2 was studied by UV–visible absorption spectrometry, fluorescence competitive, viscosity measurements and gel electrophoresis, results shown C2 can be well embedded in the double helix of DNA and cleave DNA.
- Jiang, Wujiu,Fan, Shanji,Zhou, Qian,Zhang, Fuxing,Kuang, Daizhi,Tan, Yuxing
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supporting information
(2019/11/26)
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- Synthesis of dibenzyl b stannic chloride method (by machine translation)
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The invention discloses a method for synthesizing dibenzyltin dichloride. In the tin powder and benzyl chloride reaction system, under the reaction conditions that the ratio of raw materials is not changed and reaction temperature and reaction time are not changed, the dispersing agents such as activated carbon, diatom powder, yellow sand, silica, quartz powder and kaolin are added so as to prevent the tin powder from being aggregated into blocks in the reaction process, so that the tin powder has high reaction activity, the dibenzyltin dichloride can achieve extremely high yield by using industrial grade tin powder and benzyl chloride. Meanwhile, the repeated utilization rate of the tin powder is high, and the production cost is reduced.
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Paragraph 0013; 0018; 0019; 0020; 0027
(2017/10/06)
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- Alkyl tin compound
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An alkyl tin compound having an alkyl group bound to a tin atom, wherein the alkyl group is a branched alkyl group or an alkyl group substituted by a cyclic group, the branched alkyl group is branched at at least one carbon atom among the first to third carbon atoms as counted from the tin atom, and the alkyl group substituted by a cyclic group is an alkyl group in which the cyclic group is bound to at least one carbon atom among the first to third carbon atoms as counted from the tin atom.
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Paragraph 0977; 0978; 0979
(2016/10/09)
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- Synthesis of dineophyltin dihydride and stereoselective hydrostannation of alkynes and (E)-trisubstituted alkenes
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This paper reports the synthesis of dineophyltin dihydride (3) following two procedures. The four steps synthesis starting from benzyl chloride and Sn was shown to be more convenient than the two step direct alkylation of SnCl 4. The study of the free radical hydrostannation of mono- and disubstituted acetylenes with hydride 3 shows that they are stereoselective and that the stereoisomers obtained in higher proportion are stable and easily separated by column chromatography. Some preliminary studies on the chemical reactivity of the new divinylsubstituted dineophyltin compounds in Stille reactions are also informed. Radical hydrostannatation of (E)-trisubstituted ethylenes with 3 did not succeed probably due to steric factors. The preparation of dineophyltin bromohydride (27) is also reported. Radical addition of 27 to methyl (E)-2,3-disubstituted propenoates leads to mixtures of the corresponding erythro and threo adducts in diastereomeric excesses (d.e.) in the range of 74-90%.
- Zú?iga, Adriana E.,Fidelibus, Pablo M.,Mandolesi, Sandra D.,Podestá, Julio C.
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p. 1547 - 1555
(2011/06/17)
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- Process for the preparation of organotin compounds useful as cytotoxic agents
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The present invention is drawn to complexes of dibenzyl-organotin compounds having nitrogen or sulfur containing heterocyclic ligands. Said complexes are useful as cytotoxic agents.
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- THE PHOTOLYSIS OF BENZYLTIN COMPOUND INVESTIGATED BY 1H CIDNP
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The photochemical decomposition of (PhCH2)3SnMe and (PhCH2)3SnCl has been investigated by steady-state and time-resolved chemically induced nuclear polarization (CIDNP) 1H spectroscopy of the methylene protons using 308 nmp ulses of an excimer laser and a 250 MHz NMR spectrometer.From the sign of the polarization it is concluded that (PhCH2)3SnMe reacts like other comparable tin compounds via triplet radical pairs; the CIDNP effects are not influenced by the solvent.In contrast the CIDNP effects of (PhCH2)3SnCl are solvent dependent: in C6D6 the polarization is accounted for by a singlet radical pair precursor, while in CDCl3 both singlet and triplet radical pairs are formed.The formation of singlet radical pairs during the reaction of (PhCH2)3SnCl in C6D6 may be interpreted as evidence for stannylene formation.
- Standt, Adelheit,Dreeskamp, Herbert
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- Reactions of Thionyl Chloride with Tetraorganotin(IV) Compounds
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The reactions of thionyl chloride with tetraorganotin(IV) derivatives (R4Sn where R = CH3, C2H5, n-C3H7, n-C4H9, C6H5CH2, C6H4CH3) bring about cleavage of tin-carbon bonds to give dialkyl/aryltin(IV) and alkyl/aryl sulphinyl chlorides.The ease of cleavage observed on the basis of the reactivities of R4Sn follows the order: n-C4H9 > n-C3H7 > C2H5 > CH3 > C6H5CH2 >> C6H4CH3.This order is not the same as commonly known in literature.
- Narula, Suraj P.,Sharma, R. K.,Lata, Sneh,Walia, Rita
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p. 246 - 247
(2007/10/02)
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