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Journal articles on the topic 'Dithiocarbamates'

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Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Halimehjani, Azim Ziyaei, Reza Mohtasham, Abbas Shockravi, and Jürgen Martens. "Multicomponent synthesis of dithiocarbamates starting from vinyl sulfones/sulfoxides and their use in polymerization reactions." RSC Advances 6, no. 79 (2016): 75223–26. http://dx.doi.org/10.1039/c6ra15616a.

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2

Maurya, Chandan, and Sangeeta Bajpai. "Biological Applications of Metal Complexes of Dithiocarbamates." Journal of Applied Science and Education (JASE) 2, no. 1 (March 1, 2022): 1–16. http://dx.doi.org/10.54060/jase/002.01.002.

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Dithiocarbamates are organosulphur ligands and form chelate compounds with metals. Their uses are reported in the field of accelerating vulcanization, pesticide, material science, organic synthesis, etc. Recent research demonstrated the potential of metal complexes of these ligands as good antifungal, antibacterial, and antitumor agents. Dithiocarbamate complexes have also been reported to use as a plasmonic sensor, as an inhibitor of proteasome, and for antioxidant and antileishmanial activity. This brief review presents the biological activities of metal complexes of dithiocarbamate.

3

Pedras, M. Soledade, and Francis I. Okanga. "Metabolism of analogs of the phytoalexin brassinin by plant pathogenic fungi." Canadian Journal of Chemistry 78, no. 3 (March 1, 2000): 338–46. http://dx.doi.org/10.1139/v00-024.

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he metabolism of analogs of the cruciferous phytoalexin brassinin by the phytopathogenic fungi Phoma lingam (Tode ex Fr.) "virulent" and "avirulent" groups (sexual stage Leptosphaeria maculans (Desm.) Ces. et de Not.) and Alternaria brassicae (Berk.) Sacc. is reported. It was established that each pathogen detoxified methyl tryptamine dithiocarbamate, although yielding different metabolic products. While the biotransformation by virulent P. lingam proceeded to yield methyl 3a-hydroxy-3,3a,8,8a-tetrahydropyrrolo[2,3-b]indol-1(2H)-yl carbodithioate and indole-3-acetic acid as final products, avirulent P. lingam yielded indole-3-carboxylic acid via Nb-acetyltryptamine, and A. brassicae yielded Nb-acetyltryptamine, as final products. Furthermore, to establish the importance of the dithiocarbamate group in antifungal activity against P. lingam and A. brassicae, carbamates were compared with dithiocarbamates and it was established that carbamates were devoid of antifungal activity. These products, contrary to methyl tryptamine dithiocarbamate, showed no inhibitory activity against either pathogen.Key words: Alternaria brassicae, brassinin, carbamates, detoxification, dithiocarbamates, Leptosphaeria maculans, Phoma lingam, phytoalexins.

4

Oliveira, Johny Wysllas de Freitas, Hugo Alexandre Oliveira Rocha, Wendy Marina Toscano Queiroz de Medeiros, and Marcelo Sousa Silva. "Application of Dithiocarbamates as Potential New Antitrypanosomatids-Drugs: Approach Chemistry, Functional and Biological." Molecules 24, no. 15 (August 1, 2019): 2806. http://dx.doi.org/10.3390/molecules24152806.

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Dithiocarbamates represent a class of compounds that were evaluated in different biomedical applications because of their chemical versatility. For this reason, several pharmacological activities have already been attributed to these compounds, such as antiparasitic, antiviral, antifungal activities, among others. Therefore, compounds that are based on dithiocarbamates have been evaluated in different in vivo and in vitro models as potential new antimicrobials. Thus, the purpose of this review is to present the possibilities of using dithiocarbamate compounds as potential new antitrypanosomatids-drugs, which could be used for the pharmacological control of Chagas disease, leishmaniasis, and African trypanosomiasis.

5

Tella, Toluwani, Carolina H. Pohl, and Ayansina Ayangbenro. "A review of the therapeutic properties of dithiocarbamates." F1000Research 11 (February 28, 2022): 243. http://dx.doi.org/10.12688/f1000research.109553.1.

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The persistence of infectious diseases that continue to plague the world, as well as the formation of harmful substances within the human body, such as free radicals and reactive oxygen species (ROS) have sparked new research. Thus, the need for innovative approaches for developing new or modification of existing therapeutic agents. The design of biologically important metal complexes of dithiocarbamates (DTCs) has been made possible by recent advancements in innovative research. Dithiocarbamates are reduced thiuram disulfides with excellent complexing capabilities and have various applications. They are potent and work in tandem with the core metal ions of coordinating compounds to produce synergistic effects. Dithiocarbamates have many uses, including as antidotes for metal poisoning, cisplatin or carboplatin toxicity, and clinical trials for cancer, Lyme disease, human immunodeficiency virus and antibiotics. They exert anti-oxidant effect in cells. The understanding of the mechanisms of action of this therapeutic agent is important in drug repurposing. This review highlights the protective and therapeutic properties of dithiocarbamate compounds in biological systems.

6

Ahmad, Jimmy, Fiona N. F. How, Siti Nadiah Abdul Halim, Mukesh M. Jotani, See Mun Lee, and Edward R. T. Tiekink. "A new structural motif for cadmium dithiocarbamates: crystal structures and Hirshfeld surface analyses of homoleptic zinc and cadmium morpholine dithiocarbamates." Zeitschrift für Kristallographie - Crystalline Materials 234, no. 5 (May 27, 2019): 341–49. http://dx.doi.org/10.1515/zkri-2018-2141.

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Abstract The crystal and molecular structures of two homoleptic morpholine-derived dithiocarbamates of zinc, binuclear {Zn[S2CN(CH2CH2)2O)2]2}2 (1), and cadmium, one-dimensional coordination polymer {Cd[S2CN(CH2CH2)2O)2]2}2 (2), are described. In 1, a centrosymmetric binuclear molecule is found as there are equal numbers of chelating and bidentate bridging dithiocarbamate ligands; weak transannular Zn···S interactions are found within the resultant eight-membered {···SCSZn}2 ring which has the form of a chair. The resultant 4+1 S5 donor set is highly distorted with the geometry tending towards a square-pyramid. By contrast, a square-planar geometry is found in centrosymmetric 2 defined by symmetrically chelating dithiocarbamate ligands. The presence of Cd···S secondary bonding in the crystal of 2 leads to a distorted 4+2 S6 octahedron and a linear coordination polymer, which is unprecedented in the structural chemistry of cadmium dithiocarbamates. The analyses of the Hirshfeld surfaces for 1 and 2 show the dominance of H···H, S···H/H···S and O···H/H···O contacts to the surface, i.e. contributing around 90 and 80%, respectively.

7

Begum, B., A. Sarker, AKM Lutfor Rahman, and NC Bhoumik. "Synthesis and characterization of mixed ligand catecholato-bis (diamine-mono-dithiocarbamato) vanadium (IV) complexes." Bangladesh Journal of Scientific and Industrial Research 52, no. 2 (June 13, 2017): 89–96. http://dx.doi.org/10.3329/bjsir.v52i2.32913.

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Diamine-mono-dithiocarbamates are mono-basic bidentate ligand forming stable complexes with transition metals. Mixed ligand catecholato-bis (diamine-mono-dithiocarbamato) vanadium (IV) complexes were synthesized and characterized using FT-IR, UV-visible and 1H-NMR spectroscopic techniques. The formation of vanadium complexes was con?rmed by the disappearance of ?S-H band in the complexes which was present in the ligands and incidence of ?V-S and ?V-O band in FT-IR spectra of the complexes. The mono-dithiocarbamate with one uncoordinated ?NH/NH2 group was indicated by the presence of ?N-H vibrational band in both the ligands and complexes. In the 1H-NMR spectra, the peak for SH proton of ligands disappeared in the complexes suggest the formation of [VL2Cat] complex. Non-electrolytic nature of the synthesized complexes was established by their low molar conductance values. The +4 oxidation state of vanadium was con?rmed by the electronic spectra of the complexes. On the basis of all physico-chemical data, a six-coordinated octahedral structure has been suggested for catecholato-bis (diamine-mono-dithiocarbamato) vanadium (IV) complexes.Bangladesh J. Sci. Ind. Res. 52(2), 89-96, 2017

8

Versloot, P., J. G. Haasnoot, J. Reedijk, M. van Duin, and J. Put. "Sulfur Vulcanization of Simple Model Olefins, Part IV: Vulcanizations of 2,3-Dimethyl-2-Butene with TMTD and Activated Zinc Dithiocarbamate/Xanthate Accelerators at Different Temperatures." Rubber Chemistry and Technology 68, no. 4 (September 1, 1995): 563–72. http://dx.doi.org/10.5254/1.3538757.

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Abstract The mechanism of the accelerated sulfur vulcanization of rubber was studied by the use of 2,3-dimethyl-2-butene (C6H12, TME) as a simple, low-molecular model alkene. Treatment of TME with a mixture of ZnO, S8 and the classical accelerator TMTD at temperatures above 100°C yields a mixture of addition products ((C6H11—Sn—C6H11) ). In the temperature range of 50 up to 100 °C only intermediate products, C6H11—Sn—S(S)CN(CH3)2 are obtained. Room temperature vulcanization is feasible using highly reactive accelerators, such as xanthate derivatives. These derivatives result in formation of the crosslink precursors which are converted to the actual crosslink in the presence of zinc dithiocarbamates. The addition of (secondary) amines enhances the solubility of the dithiocarbamates, and therefore the reactivity of the xanthate/zinc dithiocarbamate combination.

9

Dogheim, Salwa M., Sohair A. Gad Alla, Ashraf M. El-Marsafy, and Safaa M. Fahmy. "Monitoring Pesticide Residues in Egyptian Fruits and Vegetables in 1995." Journal of AOAC INTERNATIONAL 82, no. 4 (July 1, 1999): 948–55. http://dx.doi.org/10.1093/jaoac/82.4.948.

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Abstract Organophosphorus, dithiocarbamates, and some synthetic pyrethroids pesticides, which are commonly used in Egypt for pest control, were monitored, as well as persistent organochlorines, which had been prohibited from use several years ago. Fruit and vegetable samples (397) were collected from 8 local markets and examined for 52 pesticides. Of all analyzed samples, 42.8% contained detectable residues, of which 1.76% exceeded their maximum residue limits (MRLs). The rates of contamination with the different pesticides were 0-86%. However, violation rates among contaminated products were very low, ranging from 0 to 4.6%. In general, organochlorine pesticide residues were not detected in most samples. Dithiocarbamate residues were found in 70.4% of 98 samples analyzed for dithiocarbamates, but only one grape sample had residues exceeding the MRL established by the Codex Committee on Pesticide Residues.

10

Bala, Veenu. "Dithiocarbamates." Synlett 25, no. 05 (January 23, 2014): 746–47. http://dx.doi.org/10.1055/s-0033-1340637.

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11

Odularu, Ayodele T., and Peter A. Ajibade. "Dithiocarbamates: Challenges, Control, and Approaches to Excellent Yield, Characterization, and Their Biological Applications." Bioinorganic Chemistry and Applications 2019 (February 6, 2019): 1–15. http://dx.doi.org/10.1155/2019/8260496.

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Progresses made in previous researches on syntheses of dithiocarbamates led to increase in further researches. This paper reviews concisely the challenges experienced during the synthesis of dithiocarbamate and mechanisms to overcome them in order to obtain accurate results. Aspects of its precursor’s uses to synthesize adducts, nanoparticles, and nanocomposites are reported. Some common characterization techniques used for the synthesized products were assessed. Biological applications are also reported.

12

Gallio, Andrea E., Leonardo Brustolin, Nicolò Pettenuzzo, and Dolores Fregona. "Binuclear Heteroleptic Ru(III) Dithiocarbamate Complexes: A Step towards Tunable Antiproliferative Agents." Inorganics 10, no. 3 (March 17, 2022): 37. http://dx.doi.org/10.3390/inorganics10030037.

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Binuclear dithiocarbamate complexes of Ru(III) are promising candidates in the search for outstanding metal-based anticancer agents. While different dithiocarbamates have shown ligand-dependent cytotoxicity in homoleptic binuclear Ru(III) complexes, the properties of heteroleptic analogues with different dithiocarbamate (DTC) ligands have yet to be explored. We herein propose the introduction of heteroleptic ligands as tunable features for the development of improved ruthenium-based antiproliferative agents and report a synthetic strategy for their synthesis as well as the evaluation of the cytotoxic activity of a selection of binuclear heteroleptic Ru(III) compounds towards MDA-MB-231 and PC3 cells.

13

Hogarth, Graeme, and Damian C. Onwudiwe. "Copper Dithiocarbamates: Coordination Chemistry and Applications in Materials Science, Biosciences and Beyond." Inorganics 9, no. 9 (September 10, 2021): 70. http://dx.doi.org/10.3390/inorganics9090070.

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Copper dithiocarbamate complexes have been known for ca. 120 years and find relevance in biology and medicine, especially as anticancer agents and applications in materials science as a single-source precursor (SSPs) to nanoscale copper sulfides. Dithiocarbamates support Cu(I), Cu(II) and Cu(III) and show a rich and diverse coordination chemistry. Homoleptic [Cu(S2CNR2)2] are most common, being known for hundreds of substituents. All contain a Cu(II) centre, being either monomeric (distorted square planar) or dimeric (distorted trigonal bipyramidal) in the solid state, the latter being held together by intermolecular C···S interactions. Their d9 electronic configuration renders them paramagnetic and thus readily detected by electron paramagnetic resonance (EPR) spectroscopy. Reaction with a range of oxidants affords d8 Cu(III) complexes, [Cu(S2CNR2)2][X], in which copper remains in a square-planar geometry, but Cu–S bonds shorten by ca. 0.1 Å. These show a wide range of different structural motifs in the solid-state, varying with changes in anion and dithiocarbamate substituents. Cu(I) complexes, [Cu(S2CNR2)2]−, are (briefly) accessible in an electrochemical cell, and the only stable example is recently reported [Cu(S2CNH2)2][NH4]·H2O. Others readily lose a dithiocarbamate and the d10 centres can either be trapped with other coordinating ligands, especially phosphines, or form clusters with tetrahedral [Cu(μ3-S2CNR2)]4 being most common. Over the past decade, a wide range of Cu(I) dithiocarbamate clusters have been prepared and structurally characterised with nuclearities of 3–28, especially exciting being those with interstitial hydride and/or acetylide co-ligands. A range of mixed-valence Cu(I)–Cu(II) and Cu(II)–Cu(III) complexes are known, many of which show novel physical properties, and one Cu(I)–Cu(II)–Cu(III) species has been reported. Copper dithiocarbamates have been widely used as SSPs to nanoscale copper sulfides, allowing control over the phase, particle size and morphology of nanomaterials, and thus giving access to materials with tuneable physical properties. The identification of copper in a range of neurological diseases and the use of disulfiram as a drug for over 50 years makes understanding of the biological formation and action of [Cu(S2CNEt2)2] especially important. Furthermore, the finding that it and related Cu(II) dithiocarbamates are active anticancer agents has pushed them to the fore in studies of metal-based biomedicines.

14

Tiekink, Edward R. T. "On the Coordination Role of Pyridyl-Nitrogen in the Structural Chemistry of Pyridyl-Substituted Dithiocarbamate Ligands." Crystals 11, no. 3 (March 14, 2021): 286. http://dx.doi.org/10.3390/cryst11030286.

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A search of the Cambridge Structural Database was conducted for pyridyl-substituted dithiocarbamate ligands. This entailed molecules containing both an NCS2− residue and pyridyl group(s), in order to study their complexation behavior in their transition metal and main group element crystals, i.e., d- and p-block elements. In all, 73 different structures were identified with 30 distinct dithiocarbamate ligands. As a general observation, the structures of the transition metal dithiocarbamates resembled those of their non-pyridyl derivatives, there being no role for the pyridyl-nitrogen atom in coordination. While the same is true for many main group element dithiocarbamates, a far greater role for coordination of the pyridyl-nitrogen atoms was evident, in particular, for the heavier elements. The participation of pyridyl-nitrogen in coordination often leads to the formation of dimeric aggregates but also one-dimensional chains and two-dimensional arrays. Capricious behaviour in closely related species that adopted very different architectures is noted. Sometimes different molecules comprising the asymmetric-unit of a crystal behave differently. The foregoing suggests this to be an area in early development and is a fertile avenue for systematic research for probing further crystallization outcomes and for the rational generation of supramolecular architectures.

15

Thebti, Amal, Ines Chniti, Med Abderrahmane Sanhoury, Ikram Chehidi, Hadda Imene Ouzari, and Abdellatif Boudabous. "Antimicrobial Activity of Highly Fluorinated Thiocarbamates and Dithiocarbamates." Current Chemical Biology 13, no. 2 (July 12, 2019): 120–28. http://dx.doi.org/10.2174/2212796812666180907153901.

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Background:The widespread occurrence of resistance to current antibiotics has triggered increasing research efforts to design and develop innovative antibacterial and antifungal agents that could overcome such antimicrobial resistance.Objective:The aim of this work was the in vitro evaluation of twelve highly fluorinated Nmonosubstituted thiocarbamates and dithiocarbamates and six non-fluorinated analogs against nine bacterial strains and three fungal species.Methods:The in vitro antimicrobial activity against the tested microrganisms was evaluated using the microdilution broth method.Results:Escherichia coli ATCC 8739, Salmonella sp., Staphylococcus aureus 6539 and all the three fungi (Aspergillus niger, Aspergillus flavus and Penicillium expansum) exhibited the highest rate of susceptibility, whilst Enterococcus faecuim ATCC 19436 and particularly Escherichia coli DH5α were less susceptible. Thiocarbamate (1i) and dithiocarbamate (2i) showed both the lowest MIC values (3.9 µg/mL) and the widest spectrum of antibacterial activity. Furthermore, the N-ethyl derivatives inhibited more efficiently the growth of bacteria than N-aryl analogs.Conclusion:The fluorinated compounds showed, in general, a relatively more potent antibacterial activity than non-fluorinated counterparts. The results indicate that these thiocarbamates and dithiocarbamates could be promising candidates as potential antimicrobial agents.

16

Humeres, Eduardo, Byung Sun Lee, and Nito Angelo Debacher. "Mechanisms of Acid Decomposition of Dithiocarbamates. 5. Piperidyl Dithiocarbamate and Analogues." Journal of Organic Chemistry 73, no. 18 (September 19, 2008): 7189–96. http://dx.doi.org/10.1021/jo801015t.

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17

Halimehjani, Azim Ziyaei, Martin Dračínský, and Petr Beier. "One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent." Beilstein Journal of Organic Chemistry 13 (November 24, 2017): 2502–8. http://dx.doi.org/10.3762/bjoc.13.247.

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A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni’s reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C–N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments.

18

Saiyed, Tanzimjahan A., Jerry O. Adeyemi, and Damian C. Onwudiwe. "The structural chemistry of zinc(ii) and nickel(ii) dithiocarbamate complexes." Open Chemistry 19, no. 1 (January 1, 2021): 974–86. http://dx.doi.org/10.1515/chem-2021-0080.

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Abstract Dithiocarbamate complexes are of immense interest due to their diverse structural properties and extensive application in various areas. They possess two sulfur atoms that often act as the binding sites for metal coordination in a monodentate, bidentate, or anisodentate fashion. These different coordination modes enhance the possibility for complex formation and make them useful in different areas especially in biomedical fields. A synergy exists in the metal ions and dithiocarbamate moieties, which tends to exert better properties than the respective individual components of the complex. These improved properties have also been attributed to the presence of the C–S bonds. Zinc and nickel ions have been majorly found to bind to the dithiocarbamate in bidentate modes, and consequently different geometries have resulted from this interaction. The aim of this review is to present some studies on the synthesis, structural chemistry, and the relevance of zinc and nickel dithiocarbamates complexes especially in biological systems.

19

Abd Aziz, Nurul Amalina, Normah Awang, Kok Meng Chan, Nurul Farahana Kamaludin, and Nur Najmi Mohamad Anuar. "Organotin (IV) Dithiocarbamate Compounds as Anticancer Agents: A Review of Syntheses and Cytotoxicity Studies." Molecules 28, no. 15 (August 3, 2023): 5841. http://dx.doi.org/10.3390/molecules28155841.

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Organotin (IV) dithiocarbamate has recently received attention as a therapeutic agent among organotin (IV) compounds. The individual properties of the organotin (IV) and dithiocarbamate moieties in the hybrid complex form a synergy of action that stimulates increased biological activity. Organotin (IV) components have been shown to play a crucial role in cytotoxicity. The biological effects of organotin compounds are believed to be influenced by the number of Sn-C bonds and the number and nature of alkyl or aryl substituents within the organotin structure. Ligands target and react with molecules while preventing unwanted changes in the biomolecules. Organotin (IV) dithiocarbamate compounds have also been shown to have a broad range of cellular, biochemical, and molecular effects, with their toxicity largely determined by their structure. Continuing the investigation of the cytotoxicity of organotin (IV) dithiocarbamates, this mini-review delves into the appropriate method for synthesis and discusses the elemental and spectroscopic analyses and potential cytotoxic effects of these compounds from articles published since 2010.

20

Katritzky, Alan R., Shailendra Singh, Prabhu P. Mohapatra, Nicole Clemens, and Kostyantyn Kirichenko. "Synthesis of functionalised dithiocarbamates via N-(1-benzotriazolylalkyl)dithiocarbamates." Arkivoc 2005, no. 9 (February 1, 2005): 63–79. http://dx.doi.org/10.3998/ark.5550190.0006.908.

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21

Humeres, Eduardo, Nito A. Debacher, M. Marta de S. Sierra, José Dimas Franco, and Aldo Schutz. "Mechanisms of Acid Decomposition of Dithiocarbamates. 1. Alkyl Dithiocarbamates." Journal of Organic Chemistry 63, no. 5 (March 1998): 1598–603. http://dx.doi.org/10.1021/jo971869b.

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22

Liesivuori, Jyrki, and Kai Savolainen. "Chapter 5 Dithiocarbamates." Toxicology 91, no. 1 (June 1994): 37–42. http://dx.doi.org/10.1016/0300-483x(94)90238-0.

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23

Borràs, Jordi, Julie Foster, Roxana Kashani, Laura Meléndez-Alafort, Jane Sosabowski, Joan Suades, and Ramon Barnadas-Rodríguez. "New Bioconjugated Technetium and Rhenium Folates Synthesized by Transmetallation Reaction with Zinc Derivatives." Molecules 26, no. 8 (April 19, 2021): 2373. http://dx.doi.org/10.3390/molecules26082373.

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The zinc dithiocarbamates functionalized with folic acid 2Zn and 3Zn were synthesized with a simple straightforward method, using an appropriated folic acid derivative and a functionalized zinc dithiocarbamate (1Zn). Zinc complexes 2Zn and 3Zn show very low solubilities in water, making them useful for preparing Tc-99m radiopharmaceuticals with a potentially high molar activity. Thus, the transmetallation reaction in water medium between the zinc complexes 2Zn or 3Zn and the cation fac-[99mTc(H2O)3(CO)3]+, in the presence of the monodentate ligand TPPTS, leads to the formation of the 2 + 1 complexes fac-[99mTc(CO)3(SS)(P)] bioconjugated to folic acid (2Tc and 3Tc). In spite of the low solubility of 2Zn and 3Zn in water, the reaction yield is higher than 95%, and the excess zinc reagent is easily removed by centrifugation. The Tc-99m complexes were characterized by comparing their HPLC with those of the homologous rhenium complexes (2Re and 3Re) previously synthesized and characterized by standard methods. Preliminary in vivo studies with 2Tc and 3Tc indicate low specific binding to folate receptors. In summary, Tc-99m folates 2Tc and 3Tc were prepared in high yields, using a one-pot transmetallation reaction with low soluble zinc dithiocarbamates (>1 ppm), at moderate temperature, without needing a subsequent purification step.

24

Oladipo, Segun D., and Bernard Omondi. "N,N′-Diarylformamidine Dithiocarbamate Ag(I) Cluster and Coordination Polymer." Molbank 2022, no. 1 (January 28, 2022): M1327. http://dx.doi.org/10.3390/m1327.

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An Ag(I)formamidine cluster Ag6L16 (1) and an Ag(I)formamidine coordination polymer Ag7(L2)2 2 (L1 = N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate and L2 = N,N′-mesityl formamidine dithiocarbamate) have been synthesized from the reactions of L1 and L2 with AgNO3 respectively. The complexes were characterized using spectroscopic and analytical methods, including single-crystal X-ray diffraction. In the structure of 1, a six vertex distorted square bi-pyramidal octahedron is formed from an Ag6 core. The N,N′-bis(2,6-disopropylphenyl) formamidine dithiocarbamate ligands stabilize this core through two main –CS2 bridging modes giving a propeller like structure. In the structure of 2, each of the two Ag(I) centers are bridged by two N,N′-mesityl formamidine dithiocarbamate ligands forming 8-member Ag2(CS2)2 metallacycles with an inversion center in the middle of the Ag—Ag argentophilic bond. The metallacycles are connected through Ag—S bonds forming ribbons in the crystallographic a-axis. The Ag(I) centers are coordinated to two N,N′-mesitylformamidine dithiocarbamates through the dithiocarbamate S atoms. The thermal decomposition of complexes 1 and 2 had similar thermograms with one major weight loss activity and the formation of elemental silver particles thereafter.

25

Kiw, Yu Min, Pierre Adam, Philippe Schaeffer, Benoît Thiébaut, Chantal Boyer, and Nicolas Obrecht. "Molecular evidence for improved tribological performances of MoDTC induced by methylene-bis(dithiocarbamates) in engine lubricants." RSC Advances 12, no. 36 (2022): 23083–90. http://dx.doi.org/10.1039/d2ra03036e.

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A newly-discovered ligand transfer from methylene-bis(dithiocarbamates) to molybdenum dithiocarbamates (MoDTC) leads to MoDTC regeneration and results in enhanced fuel economy upon engine functioning.

26

Yeo, Chien Ing, Edward R. T. Tiekink, and Jactty Chew. "Insights into the Antimicrobial Potential of Dithiocarbamate Anions and Metal-Based Species." Inorganics 9, no. 6 (June 14, 2021): 48. http://dx.doi.org/10.3390/inorganics9060048.

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Bacterial infection remains a worldwide problem that requires urgent addressing. Overuse and poor disposal of antibacterial agents abet the emergence of bacterial resistance mechanisms. There is a clear need for new approaches for the development of antibacterial therapeutics. Herein, the antibacterial potential of molecules based on dithiocarbamate anions, of general formula R(R’)NCS2(−), and metal salts of transition metals and main group elements, is summarized. Preclinical studies show a broad range of antibacterial potential, and these investigations are supported by appraisals of possible biological targets and mechanisms of action to guide chemical syntheses. This bibliographic review of the literature points to the exciting potential of dithiocarbamate-based therapeutics in the crucial battle against bacteria. Additionally, included in this overview, for the sake of completeness, is mention of the far fewer studies on the antifungal potential of dithiocarbamates and even less work conducted on antiparasitic behavior.

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Mohamad, Rapidah, Normah Awang, Nurul Farahana Kamaludin, Mukesh M. Jotani, and Edward R. T. Tiekink. "[N-Benzyl-N-(2-phenylethyl)dithiocarbamato-κ2S,S′]triphenyltin(IV) and [bis(2-methoxyethyl)dithiocarbamato-κ2S,S′]triphenyltin(IV): crystal structures and Hirshfeld surface analysis." Acta Crystallographica Section E Crystallographic Communications 72, no. 10 (September 27, 2016): 1480–87. http://dx.doi.org/10.1107/s2056989016014985.

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The crystal and molecular structures of two triphenyltin dithiocarbamates, [Sn(C6H5)3(C16H16NS2)], (I), and [Sn(C6H5)3(C7H14NO2S2)], (II), are described. In (I), the dithiocarbamate ligand coordinates the SnIVatom in an asymmetric manner, leading to a highly distorted trigonal–bipyramidal coordination geometry defined by a C3S2donor set with the weakly bound S atom approximatelytransto one of theipso-C atoms. A similar structure is found in (II), but the dithiocarbamate ligand coordinates in an even more asymmetric fashion. The packing in (I) features supramolecular chains along thecaxis sustained by C—H...π interactions; chains pack with no directional interactions between them. In (II), supramolecular layers are formed, similarly sustained by C—H...π interactions; these stack along thebaxis. An analysis of the Hirshfeld surfaces for (I) and (II) confirms the presence of the C—H...π interactions but also reveals the overall dominance of H...H contacts in the respective crystals.

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Alam, Md Najib, Swapan Kumar Mandal, and Subhas Chandra Debnath. "EFFECT OF ZINC DITHIOCARBAMATES AND THIAZOLE-BASED ACCELERATORS ON THE VULCANIZATION OF NATURAL RUBBER." Rubber Chemistry and Technology 85, no. 1 (March 1, 2012): 120–31. http://dx.doi.org/10.5254/1.3672434.

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Abstract Several zinc dithiocarbamates (ZDCs) as accelerator derived from safe amine has been exclusively studied in the presence of thiazole-based accelerators to introduce safe dithiocarbamate in the vulcanization of natural rubber. Comparison has been made between conventional unsafe zinc dimethyldithiocarbamate (ZDMC) with safe novel ZDC combined with thizole-based accelerators in the light of mechanical properties. The study reveals that thiuram disulfide and 2-mercaptobenzothiazole (MBT) are always formed from the reaction either between ZDC and dibenzothiazyledisulfide (MBTS) or between ZDC and N-cyclohexyl-2-benzothiazole sulfenamide (CBS). It has been conclusively proved that MBT generated from MBTS or CBS reacts with ZDC and produces tetramethylthiuram disulfide. The observed synergistic activity has been discussed based on the cure and physical data and explained through the results based on high-performance liquid chromatography and a reaction mechanism. Synergistic activity is observed in all binary systems studied. The highest tensile strength is observed in the zinc (N-benzyl piperazino) dithiocarbamate-accelerated system at 3:6 mM ratios. In respect of tensile strength and modulus value, unsafe ZDMC can be successfully replaced by safe ZDCs in combination with thiazole group containing accelerator.

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MENDOZA, Concepcion S., and Satsuo KAMATA. "Phenylenedimethylene Bis(dithiocarbamates) and Related Bis(dithiocarbamates) as Extractants of Silver." Analytical Sciences 13, no. 4 (1997): 661–64. http://dx.doi.org/10.2116/analsci.13.661.

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Kociok-Köhn, Gabriele, Kieran C. Molloy, and Anna L. Sudlow. "Molecular routes to Cu2ZnSnS4: A comparison of approaches to bulk and thin-film materials." Canadian Journal of Chemistry 92, no. 6 (June 2014): 514–24. http://dx.doi.org/10.1139/cjc-2013-0497.

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A range of xanthates (R′3P)2CuS2COR [R′ = Ph, R = Et (1), i-Pr (2), t-Bu (3), t-Amyl (4); R′ = PhO, R = Et (5), R′ = n-Bu, R = Et (6), Bun (7)], M(S2COR)2 [M = Sn R = Et (8); Zn, R = Et (10), i-Pr (11), n-Pr (12), n-Bu (13), n-Hex (14)], Sn(S2COEt)4 (9), Zn(S2COEt)2.TMEDA (15) have been synthesised and their thermal decomposition profiles delineated by TGA. A parallel range of dithiocarbamates (R′3P)2CuS2CN(Me)R [R′ = Ph, R = Bun (16), Bz (17)], M[S2CN(Me)R]2 [M = Sn, R = Bun (18), Bz (19); M = Zn, R = Bun (21), Bz (22)] has been similarly assessed. Although precursor combinations have been found from these systems that generate Cu2ZnSnS4 (CZTS) from either a bulk decomposition (1, 8, 10 at 400 °C/Ar; Cu2Zn1.02Sn0.74S4.6), from a doctor-bladed film (7, 8, 13 at 400 °C/Ar; Cu2Zn1.2Sn1.0S3.6), and as nanoparticles (7, 8, 13 in octadecane/oleic acid, 150 °C; Cu2Zn1.0Sn0.7S2.6), attempts to deposit CZTS by aerosol-assisted CVD has proved more challenging and only successful from the dithiocarbamates 16, 18, 21 (350 °C; Cu2Zn0.9Sn0.7). As part of this work the crystal structures of 2–5, 8, 16, and the dithiocarbamate decomposition product {Sn[S2CN(Me)Bun)]2S}2 (20) have been determined.

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Schreck, R., B. Meier, D. N. Männel, W. Dröge, and P. A. Baeuerle. "Dithiocarbamates as potent inhibitors of nuclear factor kappa B activation in intact cells." Journal of Experimental Medicine 175, no. 5 (May 1, 1992): 1181–94. http://dx.doi.org/10.1084/jem.175.5.1181.

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Dithiocarbamates and iron chelators were recently considered for the treatment of AIDS and neurodegenerative diseases. In this study, we show that dithiocarbamates and metal chelators can potently block the activation of nuclear factor kappa B (NF-kappa B), a transcription factor involved in human immunodeficiency virus type 1 (HIV-1) expression, signaling, and immediate early gene activation during inflammatory processes. Using cell cultures, the pyrrolidine derivative of dithiocarbamate (PDTC) was investigated in detail. Micromolar amounts of PDTC reversibly suppressed the release of the inhibitory subunit I kappa B from the latent cytoplasmic form of NF-kappa B in cells treated with phorbol ester, interleukin 1, and tumor necrosis factor alpha. Other DNA binding activities and the induction of AP-1 by phorbol ester were not affected. The antioxidant PDTC also blocked the activation of NF-kappa B by bacterial lipopolysaccharide (LPS), suggesting a role of oxygen radicals in the intracellular signaling of LPS. This idea was supported by demonstrating that treatment of pre-B and B cells with LPS induced the production of O2- and H2O2. PDTC prevented specifically the kappa B-dependent transactivation of reporter genes under the control of the HIV-1 long terminal repeat and simian virus 40 enhancer. The results from this study lend further support to the idea that oxygen radicals play an important role in the activation of NF-kappa B and HIV-1.

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Wu, Xiang-mei, and Guo-bing Yan. "Copper-Catalyzed Synthesis of S-Aryl Dithiocarbamates from Tetraalkylthiuram Disulfides and Aryl Iodides in Water." Synlett 30, no. 05 (February 5, 2019): 610–14. http://dx.doi.org/10.1055/s-0037-1612086.

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An efficient approach for the copper-catalyzed synthesis of aryl dithiocarbamates from aryl iodides and tetraalkylthiuram disulfides in water is described. Without additional ligand and organic solvent, the coupling reaction could provide a series of S-aryl dithiocarbamates in moderate to good yields.

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Bond, AM, R. Colton, DR Mann, and JE Moir. "Characterization of Tris(Diselenocarbamato)Cobalt(III) and Pentakis(Diselenocarbamato)Dicobalt(III) Complexes by Electrochemical, Cobalt-59 N.M.R. and Mass-Spectrometric Techniques. Comparisons With Dithiocarbamate Analogs." Australian Journal of Chemistry 39, no. 9 (1986): 1385. http://dx.doi.org/10.1071/ch9861385.

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A series of Co(RR′dsc)3 and [Co2(RR′dsc)5]+ complexes (R, R′ = two alkyl groups or one heterocyclic group; dsc = NCSe2) have been synthesized and their redox behaviour, chemical reactivity and spectroscopic properties compared with the corresponding dithiocarbamate (RR′dtc) complexes. Electrochemical oxidation of Co(RR′dsc)3 in dichloromethane at platinum electrodes occurs at potentials about 0.34 V less positive than for Co(RR′dsc)3. The formally cobalt(IV) complexes [Co(RR′dsc)3]+ can be identified as a product which is then converted into [Co2(RR′dsc)5]+ via dimerization and an internal redox reaction. Despite the enhanced thermodynamic stability implied by the redox potentials, [Co(RR′dsc)3]+ has similar kinetic stability to the analogous dithiocarbamate complexes. Co(RR′dsc)3 is reduced at fairly negative potentials on both platinum and mercury electrodes with extremely rapid loss of [RR′dsc]-. [Co(RR′dsc)3]- is therefore thermodynamically and kinetically more unstable than [Co(RR′dtc)3]- . The [Co2(RR′dsc)5]+ complexes are also more readily oxidized and harder to reduce than the sulfur analogues. Oxidation of [Co2(RR′dsc)5]+ produces [Co2(RR′dsc)5]2+ at low temperatures and fast scan rates, but no stable reduced form of the dimer is accessible on the voltammetric time scale examined. The reduction process for the dimer is consistent with the reaction [Co2(RR′dsc)5]+ +e- → Co(RR′dsc)3+ Co(RR dsc)2. Electrochemical oxidation data obtained at mercury electrodes for the diselenocarbamate complexes are complicated by adsorption but are similar to that found at platinum electrodes. This contrasts with the dithiocarbamates where a mercury electrode specific pathway is observed. Cobalt-59 n.m.r. spectroscopy in dichloromethane shows the non- equivalence of the two cobalt atoms in [Co2(RR′dsc)5]+. The chemical shifts for Co(RR′dsc)3 complexes exhibit similar substituent effects to the dithiocarbamates in cobalt-59 n.m.r. measurements as was the case in oxidative electrochemistry. Cobalt-59 n.m.r. spectroscopy and mass spectrometry demonstrate that exchange, substitution and redox reactions can lead to the formation of mixed ligand diselenocarbamate complexes and mixed dithiocarbamate/diselenocarbamate complexes for both the cobalt(III) monomers and dimers.

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Hoogenraad, T. U. "DITHIOCARBAMATES AND PARKINSON'S DISEASE." Lancet 331, no. 8588 (April 1988): 767. http://dx.doi.org/10.1016/s0140-6736(88)91573-5.

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35

Trofimova, T. P., A. N. Pushin, Ya I. Lys, and V. M. Fedoseev. "Rearrangement of cyclic dithiocarbamates." Chemistry of Heterocyclic Compounds 42, no. 3 (March 2006): 419–21. http://dx.doi.org/10.1007/s10593-006-0106-2.

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36

Ujjani, Barathi, Suzanne Lyman, Donald Winkelmann, David H. Petering, William Antholine, and Mark M. Jones. "Enhancement of cytotoxicity of bleomyein by dithiocarbamates: Formation of bis(dithiocarbamato) Cu(II)." Journal of Inorganic Biochemistry 38, no. 1 (January 1990): 81–93. http://dx.doi.org/10.1016/0162-0134(90)85009-l.

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37

Stasevych, Maryna, Viktor Zvarych, Semen Khomyak, Volodymyr Lunin, Nazarii Kopak, Volodymyr Novikov, and Mykhailo Vovk. "Proton-Initiated Conversion of Dithiocarbamates of 9,10-Anthracenedione." Chemistry & Chemical Technology 12, no. 3 (September 15, 2018): 300–304. http://dx.doi.org/10.23939/chcht12.03.300.

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38

Babic-Samardzija, K., V. M. Jovanovic, and S. P. Sovilj. "Molecular structure in correlation with electrochemical properties of mixed-ligand cobalt(III) complexes." Journal of the Serbian Chemical Society 73, no. 7 (2008): 761–70. http://dx.doi.org/10.2298/jsc0807761b.

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Four mixed-ligand cobalt(III) complexes (1-4) of the general formula [Co(Rdtc)cyclam](ClO4)2 and [Co(Rac)cyclam](ClO4)2 (cyclam = 1,4,8,11-tetra- azacyclotetradecane; Rdtc = thiomorpholine-(Timdtc) or 2-methylpiperidine-(2-Mepipdtc) dithiocarbamates; Rac = 1,1,1,5,5,5-hexafluoro-2,4-pentanedionato (Hfac) or 2,2,6,6-tetramethyl-3,5-heptanedionato (Tmhd), respectively) were electrochemically examined on a glassy carbon and an iron electrode in perchloric acid solution. The obtained results showed the influence of these complexes on hydrogen evolution, the oxygen reduction reaction and iron dissolution. The exhibited effects of the complexes on these reactions depend on structure related to the bidentate dithiocarbamato or b-diketonato ligand. The electrochemical properties of the complexes were correlated with molecular structure and parameters derived from spectral analysis and molecular modeling. .

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Tamilvanan, S. "Antimony(III) Dithiocarbamates: Synthesis, Spectral, Theoretical and Biological Activities." Asian Journal of Chemistry 34, no. 5 (2022): 1080–90. http://dx.doi.org/10.14233/ajchem.2022.23526.

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Antimony(III) dithiocarbamate complexes tris(N,N-difurfuryldithiocarbamato-S,S′)antimony(III) (1) and tris(N-furfuryl-N-(2-phenylethyl)dithiocarbamato-S,S′)antimony(III) (2) have been synthesized and characterized by CHN analysis, FT-IR, 1H NMR, 13C NMR spectra and antimicrobial studies. The characteristic thioureide ν(C-N) bands occur at 1459 and 1469 cm-1 for complexes 1 and 2, respectively. 1H NMR and 13C NMR chemical shifts have been calculated using GIAO approach and the calculated chemical shifts shows good agreement with experiential shifts. The computational calculations of the antimony(III) complexes have been carried out by DFT/B3LYP using LANL2DZ basis set. The FMOs, MEP, Mulliken charge distribution and chemical activity parameters were calculated at the same level of theory. The antimicrobial activities of the antimony(III) complexes were assayed at the concentrations 400 and 800 μg/mL against four bacterial (Vibrio cholera, Staphylococcus aureus, Klebsiella pneumoniae and Escherichia coli) and two fungal species (Candida albicans and Aspergillus niger) by Agar-well disc diffusion method.

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FURUTA, Saori, Fausto ORTIZ, Xiu ZHU SUN, Hsiao-Huei WU, Andrew MASON, and Jamil MOMAND. "Copper uptake is required for pyrrolidine dithiocarbamate-mediated oxidation and protein level increase of p53 in cells." Biochemical Journal 365, no. 3 (August 1, 2002): 639–48. http://dx.doi.org/10.1042/bj20011251.

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The p53 tumour-suppressor protein is a transcription factor that activates the expression of genes involved in cell cycle arrest, apoptosis and DNA repair. The p53 protein is vulnerable to oxidation at cysteine thiol groups. The metal-chelating dithiocarbamates, pyrrolidine dithiocarbamate (PDTC), diethyldithiocarbamate, ethylene(bis)dithiocarbamate and H2O2 were tested for their oxidative effects on p53 in cultured human breast cancer cells. Only PDTC oxidized p53, although all oxidants tested increased the p53 level. Inductively coupled plasma MS analysis indicated that the addition of 60μM PDTC increased the cellular copper concentration by 4-fold, which was the highest level of copper accumulated amongst all the oxidants tested. Bathocuproinedisulphonic acid, a membrane-impermeable Cu(I) chelator inhibited the PDTC-mediated copper accumulation. Bathocuproinedisulphonic acid as well as the hydroxyl radical scavenger d-mannitol inhibited the PDTC-dependent increase in p53 protein and oxidation. Our results show that a low level of copper accumulation in the range of 25–40μg/g of cellular protein increases the steady-state levels of p53. At copper accumulation levels higher than 60μg/g of cellular protein, p53 is oxidized. These results suggest that p53 is vulnerable to free radical-mediated oxidation at cysteine residues.

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Yan, Jie, Junxing Wang, and Weijian Sheng. "Iodine-Mediated Vicinal Difunctionalization of Alkenes: A Convenient Method for Building C–Se and C–S Bonds." Synlett 29, no. 12 (May 30, 2018): 1654–58. http://dx.doi.org/10.1055/s-0037-1610145.

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A novel I2-mediated procedure is developed for building C–Se and C–S bonds simultaneously from alkenes, diselenides and sodium dithiocarbamates. This difunctionalization of alkenes is carried out in the presence of I2 and air, and exhibits good characteristics such as being transition-metal-free, requiring mild reaction conditions and simple procedures. The approach provides the product β-selanylethyl dithiocarbamates with high regioselectivity and in good yields. A plausible electrophilic addition mechanism is hypothesized.

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Garaj, J., V. Vrábel, E. Kellö, and J. Lokaj. "Crystal structures of some dithiocarbamates." Acta Crystallographica Section A Foundations of Crystallography 43, a1 (August 12, 1987): C180. http://dx.doi.org/10.1107/s0108767387080620.

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43

Koketsu, Mamoru, Toshihiro Otsuka, and Hideharu Ishihara. "SYNTHESIS OF DITHIOCARBAMATES AND SELENOTHIOCARBAMATES." Phosphorus, Sulfur, and Silicon and the Related Elements 179, no. 3 (March 1, 2004): 443–48. http://dx.doi.org/10.1080/10426500490262612.

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44

Padungros, Panuwat, and Alexander Wei. "Practical Synthesis of Aromatic Dithiocarbamates." Synthetic Communications 44, no. 16 (June 13, 2014): 2336–43. http://dx.doi.org/10.1080/00397911.2014.894527.

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45

Smirnov, Vladimir O., Anton S. Maslov, Marina I. Struchkova, Dmitry E. Arkhipov, and Alexander D. Dilman. "Synthesis of S-difluoromethyl dithiocarbamates." Mendeleev Communications 25, no. 6 (November 2015): 452–53. http://dx.doi.org/10.1016/j.mencom.2015.11.018.

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46

Altamura, Maria, Danilo Giannotti, Enzo Perrotta, Piero Sbraci, Vittorio Pestellini, Federico M. Arcamone, and Giuseppe Satta. "Synthesis of new penem dithiocarbamates." Bioorganic & Medicinal Chemistry Letters 3, no. 11 (November 1993): 2159–64. http://dx.doi.org/10.1016/s0960-894x(01)80918-5.

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Khan, Sadaf, Shahab A. A. Nami, and K. S. Siddiqi. "Piperazine pivoted transition metal dithiocarbamates." Journal of Molecular Structure 875, no. 1-3 (March 2008): 478–85. http://dx.doi.org/10.1016/j.molstruc.2007.05.020.

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Sharma, Anand Kumar. "Thermal behaviour of metal-dithiocarbamates." Thermochimica Acta 104 (August 1986): 339–72. http://dx.doi.org/10.1016/0040-6031(86)85208-x.

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Faraglia, Giuseppina, Sergio Sitran, and Diego Montagner. "Pyrrolidine dithiocarbamates of Pd(II)." Inorganica Chimica Acta 358, no. 4 (March 2005): 971–80. http://dx.doi.org/10.1016/j.ica.2004.09.063.

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Fragoso, Alex, Roberto Cao, and Maysa Baños. "Esterase activity of cyclodextrin dithiocarbamates." Tetrahedron Letters 45, no. 21 (May 2004): 4069–71. http://dx.doi.org/10.1016/j.tetlet.2004.03.156.

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