- Simultaneous determination of cobalt and nickel using morpholinedithiocarbamate (MDTC) as reagent by first and second derivative spectrophotometry
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A selective and sensitive derivative method has been proposed for the simultaneous determination of trace amounts of Co(II) and Ni(II) with morpholinedithiocarbamate (MDTC) in the presence of sodium lauryl sulphate (SLS). The molar absorption coefficients of the 1:2 complex of Co(II) and Ni(II) at 326 nm and 322 nm are 2.248 × 104 and 2.505 × 10 4 L mol-1 cm-1 for zero order. The analytical sensitivity for the second derivative of Co(II) and Ni(II) complexes are 0.0044 μg mL-1 and 0.0060 μg mL-1. The developed derivative procedure, using the zero-crossing technique, has been successfully applied for the analysis of Co(II) and Ni(II) simultaneously in different alloy samples.
- Kaur, Varinder,Malik, Ashok Kumar,Verma, Neelam
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- Synthesis, crystal structures and anticancer studies of morpholinyldithiocarbamato Cu(II) and Zn(II) complexes
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Cu(II) and Zn(II) morpholinyldithiocarbamato complexes, formulated as [Cu(MphDTC)2] and [Zn(μ-MphDTC)2(MphDTC)2], where MphDTC is morpholinyldithiocarbamate were synthesized and characterized by elemental analysis, spectroscopic techniques and single-crystal X-ray crystallography. The molecular structure of the Cu(II) complex revealed a mononuclear compound in which the Cu(II) ion was bonded to two morpholinyl dithiocarbamate ligands to form a four-coordinate distorted square planar geometry. The molecular structure of the Zn(II) complex was revealed to be dinuclear, and each metal ion was bonded to two morpholinyl dithiocarbamate bidentate anions, one acting as chelating ligand, the other as a bridge between the two Zn(II) ions. The anticancer activity of the morpholinyldithiocarbamate ligand, Cu(II) and Zn(II) complexes were evaluated against renal (TK10), melanoma (UACC62) and breast (MCF7) cancer cells by a Sulforhodamine B (SRB) assay. Morpholinyldithiocarbamate was more active than the standard drug parthenolide against renal and breast cancer cell lines, and [Zn(μ-MphDTC)2(MphDTC)2] was the most active complex against breast cancer. The copper(II) complex had a comparable activity with the standard against renal and breast cancer cell lines but showed an enhanced potency against melanoma when compared to parthenolide.
- Ajibade, Peter A.,Andrew, Fartisincha P.,Botha, Nandipha L.,Solomane, Nolwazi
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- Synthesis and crystal structure of bis(morpholino dithiocarbamato) Cd(II) complex and its use as precursor for CdS quantum dots using different capping agents
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Cadmium(II) morpholine dithiocarbamate complex [Cd(morphdtc)2] was synthesized and characterized by single crystal X-ray crystallography. The molecular structure of the complex showed Cd(II) ion in a distorted 4 + 2 octahedral geometry, in which the two morpholine dithiocarbamates act as bidentate chelating and the central Cd ion bond the sulfur atoms of adjacent morpholine acting as bridging ligands to form centrosymmetric five coordinate dimeric molecules. The Cd(II) complex was thermolysed at 180°C to prepare CdS nanoparticles using three different capping agents. The pXRD patterns revealed a mixture of hexagonal and cubic crystalline phases of CdS nanocrystals. TEM images revealed semi-spherical and spherical nanoparticles, with the size range of 4.50–5.70 nm for OLM-CdS, 3.33–5.96 nm for HDA-CdS, and 3.00–5.83 nm for ODA-CdS. The particle size distribution of the CdS nanocrystallite is within the range 1.06 nm (SD ± 0.73) for OLM-CdS, 0.68 nm, (SD ±0.73) for HDA-CdS and 1.18 nm, (SD ± 0.60) for ODA-CdS. The lattice fringes showed that the particles are almost in the same environment with the interplanar of 0.32 nm for OLM-CdS, 0.34 nm for HDA-CdS, and 0.32 nm ODA-CdS. The band gaps energy were confirmed to be 1.59 eV for OLM-CdS, 1.65 eV for HDA-CdS, and 1.62 eV for ODA-CdS nanoparticles, respectively.
- Mphahlele, Lebogang L. R.,Ajibade, Peter A.
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- Structure and characterization of tris(4-morpholinedithiocarbamato-S, S′)cobalt(·)-acetonitrile solvate complex:[Co(S2CNC4H8O)3]·CH3CN
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The crystal and molecular structure of the complex [Co(S2CNC4H8O)3]·CH3CN has been determined by X-ray crystallography. The compound crystallizes in the triclinic system, space group P1, with lattice parameters a = 10.561(2), b = 11.114(2), c = 13.011(3) A, α = 103.88(3), β= 101.58(3), γ = 114.91(1)°, and Z = 2. X-ray analysis reveals that the cobalt(III) atom is located at the apparent intersection of D3 symmetry. 'Despite the apparent presence of the rotational axes, all of the atoms in the structure were found to be unique; there are no symmetry-related atoms. The central cobalt atom is octahedrally coordinated by an arrangement of six S atoms. The octahedron is distorted as a result of the forced configuration of the four-membered chelate ring. The average Co-S distance is 2.273 A. The FT-IR spectra clearly show there are acetonitrile molecules in the crystal lattice.
- Zhang, Jiangrun,Jian, Fangfang,Lu, Lude,Yang, Xujie,Wang, Xin
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- Transesterification reactions of dimethoxycarbonylethyltin- morpholinodithiocarbamate, [(MeO2CCH2CH2)2Sn(MDTC)2]: Synthesis, spectroscopy, X-ray structural characterization and DFT calculations of new diestertin dithiocarbamate complexes – Part II
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The scarcity of studies concerning diestertin(IV) dithiocarbamate complexes led us to investigate the spectroscopic and structural properties of [(RO2CCH2CH2)2Sn(MDTC)2] (R?=?Me (1) or Et (2); MDTC?=?morpholinodithiocarbamate). The reaction of [(MeO2CCH2CH2)2SnCl2] with sodium morpholinodithiocarbamate (NaMDTC) in CHCl3 afforded (1), while the transesterification reaction of (1) with EtOH in the presence of dmso yielded (2). Both diestertin(IV) complexes were characterized by elemental analysis, FTIR and multinuclear (1H, 13C and 119Sn) NMR spectroscopy, and single-crystal X-ray diffraction. Our X-ray structural analysis revealed that (1) and (2) exhibit a distorted pentagonal bipyramidal coordination geometry. In both cases, the apical positions are occupied by ester groups while the equatorial plane displays two bidentate morpholinodithiocarbamate ligands and one intramolecular C[dbnd]O?Sn interaction. The O?Sn distances amount to 2.632 (1) and 2.618?? (2). According to our supramolecular analysis, the crystal arrangement of each product is assembled by weak C–H?O and C–H?S hydrogen bonds. Finally, a DFT study of the six- and seven-coordinate forms of (1) and (2) allowed an upper-bound estimate of the intramolecular C[dbnd]O?Sn interaction energy, ?3.7?kcal?mol?1.
- de Morais,Donnici,Rodrigues,de Lima,Wardell,Nascimento,Bitzer
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- Three-Dimensional Polymeric Thallium(I) Morpholinedithiocarbamate [Tl2{S2CN(CH2)4O}2]n and Its Capability of Binding Gold(III) from Solutions: Chemisorption Synthesis of a Heteronuclear Gold(III)–Thallium(III) Complex of the Ionic Type, ([Au{S2CN(CH2)4O}2][TlCl4])n, the Role of Secondary Interactions Tl…O, Tl…S, and Au…S in the Supramolecular Self-Organization, 13C MAS NMR, and Thermal Behavior
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Crystalline polymeric thallium(I) morpholinedithiocarbamate [Tl2{S2CN(CH2)4O}2]n (I) and the heteronuclear ion–polymeric gold(III)–thalium(III) complex ([Au{S2CN(CH2)4O}2][TlCl4])n (II) are preparatively isolated and characterized by X-ray diffraction analysis and 13C MAS NMR spectroscopy. According to the X-ray diffraction data, the main structural units of compounds I and II (CIF files CCDC 1548079 and 1548080) are presented by the binuclear centrosymmetric molecule [Tl2{S2CN(CH2)4O}2], noncentrosymmetric complex cation [Au{S2CN(CH2)4O{2]+, and isomeric complex anions [TlCl4]–. The formation of the three-dimensional polymeric structure (coordination number of Tl is 7), which is not characteristic of thallium(I) dithiocarbamates, is a consequence of the participation of the secondary Tl…O and Tl…S bonds of two types in the supramolecular self-organization of compound I. Nonequivalent secondary interactions of the first type join the binuclear molecules [Tl2{S2CN(CH2)4O}2] into polymer layers, which, in turn, form the three-dimensional polymeric framework due to the secondary bonds Tl…S. The revealed ability of freshly precipitated compound I to the chemisorption of gold(III) from solutions (2 M HCl) makes it possible to obtain heteronuclear supramolecular complex II as an individual form of binding. In the structure of the latter, the pairs of stronger secondary Au…S bonds join the gold(III) cations into dimers [Au2{S2CN(CH2)4O}4]2+ of the angular structure, the structural ordering of which is achieved in the cationcationic polymeric chain ([Au2{S2CN(CH2)4O}4]2+)n of the helical type involving the pairs of less strong Au…S bonds between the adjacent binuclear units. The distorted tetrahedral anions [TlCl4]– are localized between the polymeric chains. The study of the thermal behavior of compounds I and II by simultaneous thermal analysis makes it possible to establish the character of thermal transformations of the substances and to identify Tl2S (I), TlCl, and elemental gold (II) as thermolysis products.
- Bredyuk,Loseva,Ivanov,Gowda,Antzutkin
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- Pseudo-Polymeric Mercury(II) Morpholinedithiocarbamate [Hg{S2CN(CH2)4O}2] n: Supramolecular Structure (a Role of Secondary Hg···S Bonds), 13C and 15N CP-MAS NMR Spectra, and Thermal Behavior
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Abstract: A new representative of mercury(II) dithiocarbamate complexes, crystalline bis(morpholinedithiocarbamato-S,S')mercury(II) with the pseudo-1D-polymeric structure, is preparatively synthesized. The structure is characterized by 13С and 15N MAS NMR spectroscopy and X-ray diffraction analysis (CIF file CCDC no. 1821609). Pairs of symmetric secondary Hg???S bonds (3.400 ?) combine mononuclear [Hg{S2CN(CH2)4O}2] molecules, including planar polygons [HgS4], into a linear pseudo-polymeric chain. The study of the thermal behavior shows that the two-stage mass loss detected by thermogravimetry is due to the thermal destruction of the complex with the formation of HgS and its subsequent sublimation.
- Loseva,Rodina,Ivanov
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- Interpretation of the Cytostatic Properties of Sodium Morpholyldithiocarbamate, a Chelating Agent
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The antioxidant properties of sodium morpholyldithiocarbamate (MorDTC) were studied in order to contribute to the interpretation of its antitumor activity and synergetic effect over cis-platinum.MorDTC inhibits pyrogallol autooxidation better than vitamin C but does not dismutate the superoxide radical generated by the xanthine - xanthine oxidase system.Nevertheless, the complexes formed in situ between MorDTC and Mn(II), Co(II), Ni(II), and Cu(II) to dismutate the superoxide radical with a SOD-like activity (SOD = superoxide dismutase), expressed in terms of IC 50 values within the range of 3.2 to 62 μM.The highest activity corresponds to Mn(II) and Cu(II) complexes.The possible inhibitory action of MorDTC on erythrocyte SOD was also studied in vitro; however, the results were negative.Therefore, MorDTC should dismulate the superoxide radical after chelating metals without inhibiting SOD, the enzyme playing this role in vivo. - Keywords: Dithiocarbamates; SOD inhibition; SOD mimic
- Cao, R.,Fragoso, A.,Villalonga, R.
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- Dithiocarbamates combined with copper for revitalizing meropenem efficacy against NDM-1-producing Carbapenem-resistant Enterobacteriaceae
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The worldwide prevalence of NDM-1-producing Gram-negative pathogens has drastically undermined the clinical efficacy of carbapenems, prompting a need to devise an effective strategy to preserve their clinical value. Here we constructed a focused compound library of dithiocarbamates and systematically evaluated their potential synergistic antibacterial activities combined with copper. SA09-Cu exhibited excellent inhibition against a series of clinical NDM-1-producing carbapenem-resistant Enterobacteriaceae (CRE) in restoring meropenem effect, and slowed down the development of carbapenem resistance. Enzymatic kinetic and isothermal titration calorimetry studies demonstrated that SA09-Cu was a noncompetitive NDM-1 inhibitor. The electron paramagnetic resonance (EPR) and X-ray photoelectron spectroscopy (XPS) revealed a novel inhibition mechanism, which is that SA09-Cu could convert NDM-1 into an inactive state by oxidizing the Zn(II)-thiolate site of the enzyme. Importantly, SA09-Cu showed a unique redox tuning ability, and avoided to be reduced by intracellular thiols of bacteria. In vivo experiments indicated that SA09 combined with CuGlu could effectively potentiate MER's effect against NDM-1-producing E. coli (EC23) in the murine infection model. This study provides a highly promising scaffold in developing novel inhibitors to combat NDM-1-producing CREs.
- Chen, Cheng,Yang, Ke-Wu,Zhai, Le,Ding, Huan-Huan,Chigan, Jia-Zhu
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supporting information
(2021/11/20)
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- Synthesis, characterization, and in?vitro anticancer studies of chlorido(triphenylphosphine)ruthenium(II) dithiocarbamate complexes
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Three chlorido(triphenylphosphine)ruthenium(II) dithiocarbamate complexes - [RuCl(PPh3)3(Mbzdtc)] 1, [RuCl(PPh3)3(Ppipdtc)] 2, and [RuCl(Ph3)3(Mordtc)] 3 with Mbzdtc = N-methylphenyldithiocarbamate, Ppipdtc = phenylpiperazyldithiocarbamate and (Mordtc) = morpholinyldithiocarbamate were synthesized and characterized by elemental analysis and spectroscopic techniques. The Ru(II) atom is six coordinate and displays an octahedral coordination geometry, in which it is bonded to one dithiocarbamato anion acting as bidentate ligand. Electrochemical studies indicate for complexes 1 and 2 a quasi-reversible one electron redox couple due to Ru(III)/Ru(II), whereas complex 3 showed two redox couples due to Ru(III)/Ru(II) and Ru(II)/Ru(I). The E 1/2 values observed toward the cathodic region are consequence of the presence of S-S donor atom of the dithiocarbamate ligand. The anticancer potential of the complexes was assessed using sulforhodamine B (SRB) assay against renal (TK10) melanoma (UACC62) and breast (MCF7) human cancer cell lines. Complex 1 exhibits the highest cytotoxic activity against MCF7 with an IC50 value of 33.36 μM, whereas complex 3 exhibits the lowest activity against TK10 with an IC50 value of 91.95 μM.
- Ajibade, Peter A.,Andrew, Fartisincha P.
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p. 832 - 838
(2021/05/27)
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- Synthesis, characterization, and electrochemical studies of Co(II, III) dithiocarbamate complexes
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Cobalt(II) complexes of N-methyl phenyl, 1-phenylpiperazyl, and morpholinyl dithiocarbamates have been synthesized and characterized by UV–Visible, FTIR, 1H-, 13C-NMR, and mass spectrometry. The spectroscopic data indicated that two ligands coordinated in bidentate chelating to the metal ion to form four-coordinate cobalt(II) complexes (1–3), which was confirmed by mass analysis (TOF MS ES+) of the complexes with m/z [M]+ = 450.98, 382.94, and 382.94 for 1, 2, and 3, respectively. Single crystal analysis of 2A and 3A show centrosymmetric mononuclear cobalt(III) bonded to three dithiocarbamate ligands forming a distorted octahedral geometry, indicating the cobalt(II) undergoes aerial oxidation to cobalt(III) during recrystallization. In addition, 2A crystallized with one solvated molecule of toluene. The redox behaviors of the complexes were studied by cyclic and square wave voltammetry in dichloromethane; the result revealed a metal centered redox process consisting of a one-electron quasi-reversible process assigned to Co(III)/Co(IV) oxidation and a corresponding Co(IV)/Co(III) reduction. Randles–Sevcik plots (anodic peak current versus the square root of the scan rate (Ip,a versus ν1/2)) for the redox couples revealed diffusion-controlled behavior.
- Andrew, Fartisincha P.,Ajibade, Peter A.
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p. 1171 - 1186
(2019/04/10)
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- Dithiocarbamates: Efficient metallo-β-lactamase inhibitors with good antibacterial activity when combined with meropenem
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The activity of β-lactam antibiotics is compromised by metallo-β-lactamases (MBLs). Herein, a series of dithiocarbamate derivatives were designed and synthesized. Their antibacterial activities were tested in combination with meropenem (MEM) against several MBL (NDM and IMP type)-producing clinical isolates. Clinical isolates harboring NDM-1 and IMP-4 became susceptible to MEM when it was combined with dithiocarbamate compounds 4a, 4b or 4f synthesized in this work. Compounds 4a and 4b increased the effectiveness of MEM by up to 2560 times against strains. In vitro bactericidal dynamics tests showed that bacteria died within 24 h when they were treated with compound 4f + MEM. Compounds 4a, 4b and 4f were non-hemolytic and exhibited low toxicity toward HeLa cells in vitro. These data show that compounds containing dithiocarbamate functional group may be helpful in the development of MBL inhibitors.
- Wang, Ming-Ming,Chu, Wen-Chao,Yang, Yi,Yang, Qian-Qian,Qin, Shang-Shang,Zhang, En
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supporting information
p. 3436 - 3440
(2018/09/29)
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- Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology
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Sexually transmitted diseases like trichomoniasis along with opportunistic fungal infections like candidiasis are major global health burden in female reproductive health. In this context a novel non-nitroimidazole class of substituted carbamothioic amine-1-carbothioic thioanhydride series was designed, synthesized, evaluated for trichomonacidal and fungicidal activities, and was found to be more active than the standard drug Metronidazole (MTZ). Compounds were trichomonicidal in the MIC ranges of 4.77–294.1 μM and 32.46–735.20 μM against MTZ-susceptible and -resistant strains, respectively. Further, compounds inhibited the growth of at least two out of ten fungal strains tested at MIC of 7.50–240.38 μM. The most active compound (20) of this series was 3.8 and 9.5 fold more active than the MTZ against the two Trichomonas strains tested. Compound 20 also significantly inhibited the sulfhydryl groups present over Trichomonas vaginalis and was found to be more active than the MTZ in vivo. Further, a docking analysis carried out with cysteine proteases supported their thiol inhibiting ability and preliminary pharmacokinetic study has shown good distribution and systemic clearance.
- Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Krishna, Shagun,Srivastava, Nidhi,Shukla, Mahendra,Singh, Pratiksha,Chauhan, Bhavana S.,Goyani, Ravi,Maikhuri, Jagdamba P.,Sashidhara, Koneni V.,Kumar, Brijesh,Tripathi, Renu,Shukla, Praveen K.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.
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p. 632 - 645
(2017/12/08)
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- Synthesis and biological evaluation of new cholinesterase inhibitors for Alzheimer's disease
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Alzheimer's disease (AD) is a neurodegenerative disorder mostly influencing the elderly, and causes death due to dementia. The main pathogenic feature connected with the progression of this multifactorial disease is the weakening of the cholinergic system in the brain. Cholinesterase (ChE) inhibitors are recognized as one of the choices in the treatment of AD. The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) were approved as a therapeutic strategy to reduce the symptoms of AD and prevent its progression. The capacity of BChE is not completely known yet; rather, it is accepted to assume a part in a few disorders such as AD. Thus, BChE inhibitors may have a greater role for the treatment of AD in the future. In the present study, 2-(9-acridinylamino)-2-oxoethyl piperazine/piperidine/morpholinecarbodithioate derivatives were synthesized in order to investigate anticholinesterase activity. Eight derivatives demonstrated a specific and promising action against BChE. Furthermore, compound 4n showed inhibitory activity against both enzymes. It was found that the active compounds were well tolerated in the cytotoxicity test. Possible interactions between the lead compound, 4n, and the BChE enzyme were determined through a docking study. The findings obtained within this paper will contribute to the development of new and effective synthetic anti-Alzheimer compounds, and will ideally encourage future screening against AD.
- Hussein, Weiam,Sa?lik, Begüm Nurpelin,Levent, Serkan,Korkut, Bü?ra,Ilgin, Sinem,?zkay, Yusuf,Kaplancikli, Zafer Asim
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- Synthesis and evaluation of new benzodioxole-based dithiocarbamate derivatives as potential anticancer agents and hCA-I and hCA-II inhibitors
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In the current work, new benzodioxole-based dithiocarbamate derivatives were synthesized via the reaction of N-(1,3-benzodioxol-5-ylmethyl)-2-chloroacetamide with appropriate sodium salts of N,N-disubstituted dithiocarbamic acids. These derivatives were evaluated for their cytotoxic effects on A549 human lung adenocarcinoma and C6 rat glioma cell lines. N-(1,3-Benzodioxol-5-ylmethyl)-2-[4-(4-nitrophenyl)-1-piperazinylthiocarbamoylthio]acetamide (10) can be identified as the most promising anticancer agent against C6 cell line due to its notable inhibitory effect on C6 cells with an IC50value of 23.33 ± 7.63 μg/mL when compared with cisplatin (IC50= 19.00 ± 5.29 μg/mL). On the other hand, compound 10 did not show any significant cytotoxic activity against A549 cell line. The compounds were also tested for their in vitro inhibitory effects on hCA-I and hCA-II. Generally, the tested compounds were more effective on CAs than acetazolamide, the reference agent. Among these compounds, N-(1,3-benzodioxol-5-ylmethyl)-2-[(morpholinyl)thiocarbamoylthio]acetamide (3) and N-(1,3-benzodioxol-5-ylmethyl)-2-[(thiomorpholinyl)thiocarbamoylthio]acetamide (4) were found to be the most effective compounds on hCA-I with IC50values of 0.346 nM and 0.288 nM, and hCA-II with IC50values of 0.287 nM and 0.338 nM, respectively.
- Alt?ntop, Mehlika Dilek,Sever, Belgin,Akal?n ?ift?i, Gül?en,Kucukoglu, Kaan,?zdemir, Ahmet,Soleimani, Seyedeh Sara,Nadaroglu, Hayrunnisa,Kaplanc?kl?, Zafer As?m
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p. 190 - 196
(2016/12/02)
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- Precursor dependent morphological and photo-catalytic behaviour of CdS nanostructures
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Cadmium complexes based on Xanthate and dithiocarbamate such as [Cd(ethyl xanthate)2], [Cd(morpholine-4-dithiocarbamate)2] and [Cd(piperazine1-dithiocarbamate)2] have been used as efficient single source precursors. The formation of CdS nanostructures have been achieved by solvothermal route of synthesis. Crystallographic and morphological characterization of synthesized nanomaterials has been done by X-ray diffraction (XRD) and electron microscopy [Transmission Electron Microscope (TEM)], respectively. Diffraction and electron microscope studies reveal the formation of wurtzite structured CdS nanostructures of various morphologies (nanorods and nanospheres). UV–vis absorption and Fourier transform infrared (FTIR) spectroscopic studies have been carried for the detailed optical as well as qualitative analyses. It has been reported that the morphology of synthesized nanomaterials strongly depends upon the type of the precursor complexes. Photo-catalytic activity of the synthesized nanostructures has been tested in visible irradiation using methylene blue (MB) dye as a test contaminant in aqueous media. Morphology dependent photo-catalytic activity of the synthesized nanomaterials has been studied in detail to explore the potential of prepared nanostructures to purify polluted water.
- Kaur, Balwinder,Singh, Karamjit,Malik, Ashok Kumar
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p. 352 - 359
(2016/11/25)
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- Effect of ligands on crystallography, morphology and photo-catalytic ability of ZnS nanostructures
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ZnS nanostructures have been synthesized using zinc complexes: Zn(ethyl xanthate)2] & [Zn(morpholine4-dithiocarbamate)2] from ligands potassium ethyl xanthate (KEX) and morpholine4-dithiocarbamate (MDTC) by solvothermal route of synthesis. Crystallographic and morphological analyses of synthesized ZnS nanostructures have been done by X-ray diffraction (XRD) and electron microscopy [Transmission Electron Microscope (TEM)], respectively. Diffraction and electron microscope studies reveal the formation of hexagonal structured ZnS nanocrystals of various morphologies (nanosheets & nanorods). UV–vis. absorption studies have been carried for the detailed optical analyses. Photoluminescence (PL) study was carried out to check luminescence of synthesized ZnS nanostructures in blue region of electromagnetic spectrum. It has been reported that the morphology of synthesized nanostructures strongly depends upon the precursor complexes prepared from two different classes of ligands; potassium ethyl xanthate and morpholine4-dithiocarbamate. Photo-catalytic activity potential of the synthesized ZnS nanostructures has been tested in UV light using methylene blue (MB) dye as a test contaminant in aqueous media. About 88.49% and 87.96% of MB dye was photo-degraded by ZnS nanostructures synthesized from Zn(EX)2 [ where EX stands for ethyl xanthate] and Zn(MDTC)2, respectively.
- Kaur, Balwinder,Singh, Karamjit,Malik, Ashok Kumar
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p. 153 - 160
(2017/03/23)
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- Design, synthesis and pharmacological analysis of 5-[4′-(substituted-methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles
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In the present paper 5-[4′-({4-[(4-aryloxy)methyl]-1H-1,2,3-triazol-1-yl}methyl)[1,1′-biphenyl]-2-yl]-1H-tetrazoles (5a–g) and [2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl-substituted-1-carbodithioates (11h–q) have been designed and synthesized. These compounds were subjected to docking (against AT1 receptor protein enzyme in complex with Lisinopril), in vitro angiotensin converting enzyme inhibition, anti-proliferative, anti-inflammatory screening (through egg albumin denaturation inhibition and red blood cell membrane stabilization assay) and finally anti-fungal activity analyses. Some of the compounds have shown significant pharmacological properties.
- Kamble, Atulkumar,Kamble, Ravindra,Dodamani, Suneel,Jalalpure, Sunil,Rasal, Vijaykumar,Kumbar, Mahadev,Joshi, Shrinivas,Dixit, Sheshagiri
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p. 444 - 457
(2017/04/13)
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- Role of disulfide linkage in action of bis(dialkylaminethiocarbonyl)disulfides as potent double-Edged microbicidal spermicide: Design, synthesis and biology
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Trichomoniasis and candidiasis are amongst the most common morbidity-causing reproductive tract infections, generally treated by Metronidazole and Fluconazole respectively. Poor vaginal efficacy, drug-resistance and non-spermicidal nature limit their use as topical microbicidal contraceptives. Bis(dialkylaminethiocarbonyl)disulfides (4-38) were designed as dually active, non-surfactant molecules capable of eliminating Trichomonas vaginalis and Candida strains as well as irreversibly immobilizing 100% human sperm instantly, at doses non-cytotoxic to human cervical epithelial cells and vaginal microflora in vitro. Compounds 12, 16, 17 were fifty times more active than nonoxynol-9, OTC vaginal spermicide, and compounds 12 and 17 have shown remarkable in vivo activity in rabbit model. Most promising compound 17 has shown promise for further development as a double-edged vaginal microbicide due to their improved activity and safety along with notable in vivo trichomonicidal activity. Role of disulfide group was established by loss of spermicidal activity on chemical modifications (39-56). These disulfides might be targeting thiol groups present over cell membrane of human sperm and Trichomonas as shown by fluorescence labeling of free thiols.
- Lal, Nand,Jangir, Santosh,Bala, Veenu,Mandalapu, Dhanaraju,Sarswat, Amit,Kumar, Lalit,Jain, Ashish,Kumar, Lokesh,Kushwaha, Bhavana,Pandey, Atindra K.,Krishna, Shagun,Rawat, Tara,Shukla, Praveen K.,Maikhuri, Jagdamba P.,Siddiqi, Mohammad I.,Gupta, Gopal,Sharma, Vishnu L.
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p. 275 - 290
(2016/04/26)
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- Cyclic ammonium salts of dithiocarbamic acid: stable alternative reagents for the synthesis of S-alkyl carbodithioates from organyl thiocyanates in water
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ABSTRACT: Carbodithioate esters are important functional organosulfur compounds widely used in diverse fields such as pharmaceuticals, agrochemicals and material sciences. Common preparative methods include reaction of alkyl halides, carbon disulfide and bases under both metal-free and metal-catalyzed conditions. However, organyl thiocyanates have not been previously explored, possibly because of their conversion to organyl disulfides under basic conditions. Here, we report an efficient and practical method for the preparation of libraries of carbodithioate esters from organyl thiocyanates by reacting with cyclic amine-based dithiocarbamic acid salts in water. The protocol is found to be applicable in general to various thiocyanates such as benzyl/aroyl methyl/cinnamyl and so on. Other notable features include no by-products such as disulfides, metal- and alkali-free, aqueous conditions, and finally easy and near-quantitative formation of cyclic amine-based dithiocarbamic acid salt as a stable alternative reagent.
- Biswas, Kinkar,Ghosh, Sujit,Ghosh, Pranab,Basu, Basudeb
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p. 361 - 376
(2016/07/23)
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- C5-curcuminoid-dithiocarbamate based molecular hybrids: Synthesis and anti-inflammatory and anti-cancer activity evaluation
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A series of C5-curcumin bearing morpholine based dithiocarbamates was synthesized. Molinspiration and Osiris software were used for theoretical prediction of physico-chemical properties of these molecules and the majority of the hybrids showed theoretical physico-chemical properties similar or better than curcumin. These hybrids (4a-4v) were evaluated for in vitro cytotoxicity on chronic myeloid leukemia (KBM5) and colon cancer (HCT116) cell lines, and down modulation of TNF-α-induced NF-κB activation at 5 μM. Most of the hybrids exhibit higher cytotoxicity against KBM5 cells compared to HCT116 cell lines. Further, all the hybrids showed potential to suppress the TNF-α-induced NF-κB activation at 5 μM KBM5 cells and seventeen hybrids have shown higher potential to inhibit NF-κB activation in comparison to curcumin.
- Anthwal, Amit,Singh, Kundan,Rawat,Tyagi, Amit K.,Aggarwal, Bharat B.,Rawat, Diwan S.
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p. 28756 - 28764
(2014/07/22)
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- CARBONIC ANHYDRASE INHIBITOR COMPRISING A DITHIOCARBAMATE
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A carbonic anhydrase inhibitor which comprises a compound of general formula: R 1RZN-CSz-M+ for use in the treatment of microbial infection, eye disease or cancer; wherein R1 and R2 are each independently selected from H or an organic substituent, or together form a ring, and optionally contain one or more heteroatoms; wherein R and R2 together comprise at least 5 carbon atoms or at least 2 carbon atoms and a heteroatom, or R2 comprises at least 4 carbon atoms; and wherein M+ comprises a monovalent cation
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Page/Page column 23-24
(2013/04/24)
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- Synthesis, characterization and cytotoxicity of the Au(III) complexes with cyclic amine-based dithiocarbamate ligands
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Seven new Au(III) complexes ([(PipDTC)AuCl2] (1), [(MoDTC)AuCl2] (2), [(BzoPizDTC)AuCl2] (3), [(TsPizDTC)AuCl2] (4), [(PizDTC)Au2Cl4] (5), [(MePizDTC)Au2Cl5] (6) and [(EtPizDTC)Au 2Cl5] (7)) with cyclic amine-based dithiocarbamate have been synthesized, characterized and evaluated in vitro. The results indicate that these complexes exert selective cytotoxic effects against HL-60, BGC-823, Bel-7402 and KB cells lines. Complex 1 shows 11-, 5- and 1-folds higher cytotoxicity than cisplatin against KB, BGC-823 and Bel-7402 cell lines. Complex 2 exhibits higher cytotoxicity than cisplatin against BGC-823 and Bel-7402 cell lines. Complexes 3 and 4 display higher cytotoxicity than cisplatin against BGC-823 cell line. The nature of cyclic amine and the number of metal centers have important effects on cytotoxicity of these Au(III) complexes.
- Shi, Yanan,Chu, Wenhao,Wang, Yuechai,Wang, Shuxiang,Du, Jianlong,Zhang, Jinchao,Li, Shenghui,Zhou, Guoqiang,Qin, Xinying,Zhang, Chenliang
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p. 178 - 181
(2013/07/04)
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- Synthesis and biological evaluation of a series of dithiocarbamates as new cholinesterase inhibitors
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In the present paper, a novel series of dithiocarbamates was synthesized via the treatment of 4-(trifluoromethyl)benzyl chloride with appropriate sodium salts of N,N-disubstituted dithiocarbamic acids. The chemical structures of the compounds were elucidated by 1H NMR, mass spectral data, and elemental analyses. Each derivative was evaluated for its ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) using a modification of Ellman's spectrophotometric method. The most potent AChE inhibitor was found as compound 2g (IC50 = 0.53 ± 0.001 μM) followed by compounds 2f (IC50 = 0.74 ± 0.001 μM) and 2j (IC50 = 0.89 ± 0.002 μM) when compared with donepezil (IC50 = 0.048 ± 0.001 μM). Compounds 2f and 2g were more effective than donepezil (IC50 = 7.88 ± 0.52 μM) on BuChE inhibition. Compounds 2f and 2g exhibited the inhibitory effect on BuChE with IC50 values of 1.39 ± 0.041 and 3.64 ± 0.072 μM, respectively.
- Altintop, Mehlika D.,Gurkan-Alp, A. Selen,Oezkay, Yusuf,Kaplancbox, Zafer A.
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p. 571 - 576
(2013/09/02)
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- Dithiocarbamates strongly inhibit carbonic anhydrases and show antiglaucoma action in vivo
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A series of dithiocarbamates were prepared by reaction of primary/secondary amines with carbon disulfide in the presence of bases. These compounds were tested for the inhibition of four human (h) isoforms of the zinc enzyme carbonic anhydrase, CA (EC 4.2.1.1), hCA I, II, IX, and XII, involved in pathologies such as glaucoma (CA II and XII) or cancer (CA IX). Several low nanomolar inhibitors targeting these CAs were detected. The X-ray crystal structure of the hCA II adduct with morpholine dithiocarbamate evidenced the inhibition mechanism of these compounds, which coordinate to the metal ion through a sulfur atom from the dithiocarbamate zinc-binding function. Some dithiocarbamates showed an effective intraocular pressure lowering activity in an animal model of glucoma.
- Carta, Fabrizio,Aggarwal, Mayank,Maresca, Alfonso,Scozzafava, Andrea,McKenna, Robert,Masini, Emanuela,Supuran, Claudiu T.
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experimental part
p. 1721 - 1730
(2012/05/04)
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- Biological in vitro and in vivo studies of a series of new asymmetrical cationic [99mTc(N)(DTC-Ln)(PNP)]+ Complex (DTC-Ln = alicyclic dithiocarbamate and PNP = Diphosphinoamine)
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99mTc(N)-DBODC5 is a cationic mixed compound under clinical investigation as potential myocardial imaging agent. In spite of this, analogously to the other cationic 99mTc-agents, presents a relatively low first-pass extraction. Thus, modification of 99mTc(N)-DBODC(5) direct to increase its first-pass extraction keeping unaltered the favorable imaging properties would be desirable. This work describes the synthesis and biological evaluation of a series of novel cationic 99mTc-nitrido complexes, of general formula [99mTcN(DTC-Ln)(PNP)]+ (DTC-Ln= alicyclic dithiocarbamates; PNP = diphosphinoamine), as potential radiotracers for myocardial perfusion imaging. The synthesis of cationic 99mTc-(N)-complexes were accomplished in two steps. Biodistribution studies were performed in rats and compared with the distribution profiles of 99mTc(N)-DBODC5 and 99mTc-Sestamibi. The metabolisms of the most promising compounds were evaluated by HPLC methods. Biological studies revealed that most of the complexes have a high initial and persistent heart uptake with rapid clearance from nontarget tissues. Among tested compounds, 2 and 12 showed improved heart uptake with respect to the gold standard 99mTc-complexes with favorable heart-to-liver and slightly lower heart-to-lung ratios. Chromatographic profiles of 99mTc(N)- radioactivity extracted from tissues and fluids were coincident with the native compound evidencing remarkable in vivo stability of these agents. This study shows that the incorporation of alicyclic dithiocarbamate in the [ 99mTc(N)(PNP)]+ building block yields to a significant increase of the heart uptake at early injection point suggesting that the first-pass extraction fraction of these novel complexes may be increased with respect to the other cationic 99mTc-agents keeping almost unaltered the favorable target/nontarget ratios.
- Bolzati, Cristina,Cavazza-Ceccato, Mario,Agostini, Stefania,Refosco, Fiorenzo,Yamamichi, Yoshihiro,Tokunaga, Shinji,Carta, Davide,Salvarese, Nicola,Bernardini, Daniele,Bandoli, Giuliano
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experimental part
p. 928 - 939
(2011/02/22)
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- Heterocyclo-substituted sulfa drugs: Part XI. Novel biologically active N-(piperidino-, morpholino-, piperazino-) dithiocarbamyl-azo dyes and their chelates
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A Series of novel azo-sulfa drugs of piperidino-, morpholino-, mono-, and bis-piperazino-N-dithiocarbamyl-azo dyes (Ia-h - IV a-h) are synthesiezed via a reaction of 4-[(4′-heterocyclo-substituted) suflamoyl and/or sulfonyl] benzenediazonium salts with N-piperidino-, N-morpholino-, mono-, and bis- N-piperazino- dithiocarbamate sodium salts in acid medium to afford the corresponding azo dye legands. Interaction of these ligands with metal salts: iron(III), copper(II) and mercuric(II) chlorides in ethanolic solution afforded the corresponding metal chelates (I′a-h - ′IVa-h), (I″a-h - ″IVa-h) and (I?a-h - ≈IVa-h). Ligands and their metal chelates are characterized by microanalysis, IR, UV-Vis H-NMR spectroscopy and are screened in vitro for their antimicrobial activities. Chelation of ligands induces a remarkable increase in their antimicrobial activity.
- Awad, Ibrahim M.A.
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p. 219 - 251
(2007/10/03)
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- Synthesis, characterization and evaluation of biological activity of palladium (II) and platinum (II) complexes with dithiocarbamic acids and their derivatives as ligands
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We report the preparation and characterization of new complexes of palladium (II) and platinum (II) with some heterocyclic containing dithiocarbamate ligands, such as piperidine-, morpholine-, and thiomorpholine-dithiocarbamate, their methyl esters and the corresponding thiouramdisulphides. These compounds have been studied through spectroscopic techniques, IR spectra, and electronic spectra, thermogravimetric and conductivity measurements. Thermal decomposition of the complexes takes place through a multi-step process involving pyrolysis of the organic moiety that leads to palladium oxide and platinum sponge respectively. All the complexes have been tested for cytostatic activity on KB cells and the most effective compounds also against L1210 and P388 cells.
- Marcheselli,Preti,Tagliazucchi,Cherchi,Sindellari,Furlani,Papaioannou,Scarcia
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p. 347 - 352
(2007/10/02)
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- Preparation and Characterization of Bis-Dithiocarbamato di-p-Tolyl Tin(IV)
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Bis-Dithiocarbamato di-p-tolyltin(IV), i.e., (p-CH3C6H4)2Sn(S2CNRR')2 (where R=R'=CH3, C2H5, i-C3H7; R=CH3, C2H5, i-C3H7 and R'=C6H5, CH2C6H5 or RR'=morpholine, 4-methylpiperidine and N-piperazine), were prepared by the reaction of di-p-tolyltin(IV) dichloride with the sodium salt of respective dithiocarbamate acid in acetone medium in the stoichiometric ratio of 1:2.The compounds have been duly characterized on the basis of infrared and nmr spectroscopic data.Anisobidentate nature of dithiocarbamate moiety has been suggested in these compounds.
- Wadhwa, Sangeeta,Garg, B. S.,Sharma, C. P.,Kumar, N.
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p. 247 - 250
(2007/10/02)
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- Reduction Potentials of Thiuram Disulfide/Dithiocarbamate Couples in Acetone/Water
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Reduction potentials relative to the saturated calomel electrode, Eo, of a series of thiuram disulfide/dithiocarbamate couples have been measured in 30percent v/v water in acetone and at μ 0.2 mol l-1 (NaNO3) by a combination of potentiometric measurements and equilibrium constant determinations for thiolate/disulfide interchange reactions.Eo values lie in the range -250 to -340 mV which place dithiocarbamates as intermediate between thiophenolate (Eo -540 mV) and ethylxanthate (Eo -206 mV) in reducing properties.The significant effect on Eo of varying the substituents on the nitrogen in the dithiocarbamates correlates with the substituent effects on the acid dissociation constants of the parent dithiocarbamic acid and with trends in the half-wave potentials for metal-based oxidation and reduction of transition metal dithiocarbamate complexes.
- Nichols, Peter J.,Grant, Michael W.
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p. 2455 - 2463
(2007/10/02)
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- REACTION OF DITHIOCARBAMIC ACID SALTS WITH 4-SUBSTITUTED 2-THIOLENE- AND 3,4-DISUBSTITUTED THIOLANE 1,1-DIOXIDES. STRUCTURAL STUDIES OF N-PHENYLTHIOLANOTHIAZOLIDINE-2-THIONE 5,5-DIOXIDE
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The reaction of monoalkyl(aryl)dithiocarbamic acid salts with 4-substituted 2-thiolene and 3,4-disubstituted thiolane 1,1-dioxides gave N-alkyl(aryl)thiolanothiazolidine-2-thione 5,5-dioxides, the structure of which was proved by X-ray diffraction studies. 1,1-Dioxothiol-3-en-3-yl esters were obtained with salts of dialkyl(heteryl)dithiocarbamic acids.
- Bezmenova, T. E.,Khaskin, G. I.,Slutskii, V. I.,Dul'nev, P. G.,Zakharov, L. N.,et al.
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p. 668 - 672
(2007/10/02)
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- INVESTIGATIONS OF CHROMIUM(III), MAGANESE(III), TIN(II) AND LEAD(II) DITHIOCARBAMATE COMPLEXES
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Piperidine-, morpholine-4-, N-methylpiperazine-4- and thiomorpholine-4-carbodithioate complexes of chromium(III), manganese(III), tin(II) and lead(II) are prepared and characterized by chemical analyses, spectroscopic methods (I.R. and electronic spectra), magnetic susceptibilities, conductivity measurements and mass spectra.The complexes are of the type M(R2dtc)n, where n is the oxidation number of the metal ion.Where possible a tentative stereochemistry of the complexes is discussed on the basis of the results obtained.In all the complexes the dithiocarbamate ligands show bidentate behaviour.
- Preti, Carlo,Tosi, Giuseppe,Zannini, Paolo
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p. 283 - 292
(2007/10/02)
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