- Emulsion polymerization of vinyl acetate using iodine-transfer and RAFT radical polymerizations
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This study deals with control of the molecular weight and molecular weight distribution of poly(vinyl acetate) by iodine-transfer radical polymerization and reversible addition-fragmentation transfer (RAFT) emulsion polymerizations as the first example. E
- Nomura, Naoki,Shinoda, Keiji,Takasu, Akinori,Nagata, Kenji,Inomata, Katsuhiro
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- Iodine mediated direct coupling of benzylic alcohols with dithiocarbamate anions: An easy access of S-benzyl dithiocarbamate esters under neat reaction condition
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An efficient, metal and solvent free synthesis of S-benzylic dithiocarbamate esters has been demonstrated via the iodine mediated direct C-S coupling of benzylic alcohols with dithiocarbamate anions generated in-situ by the reactions of amines and carbon disulphide. All the reactions were very fast (15–30 min) and performed under open air atmosphere. Cyclic and acyclic secondary amines, primary amine, aromatic amine actively participated in the one-pot coupling reactions with different benzylic alcohols. Non benzylic alcohols offer the synthesis of O-thiocarbamate compounds under the identical reaction condition.
- Dutta, Soumya,Saha, Amit
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- Synthetic method of dialkyl amino dithiocarbamate alkyl ester
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In organic sulfur compounds, dialkyl amino dithiocarbamate alkyl ester plays a very important role. Researches show that dialkyl amino dithiocarbamate alkyl ester and the derivatives thereof have widebiological characteristics and pharmacological activity. For example, many studies show that the dialkyl amino dithiocarbamate alkyl ester has various activities, including anti-proliferative, anti-glaucoma, antibacterial, antifungal, breast cancer treatment and cholinesterase inhibition activities, and can be used as a myocardial imaging agent. It is known that dialkyl amino dithiocarbamate alkyl ester and the derivatives thereof can be taken as inhibitors of HIV-1 NCp7, antiviral agents, and non-flavonoid TRPV1 antagonists. Dialkyl amino dithiocarbamate alkyl ester has a wide application range, and is massively produced in the world. The invention provides a method for efficiently synthesizing dialkyl amino dithiocarbamate alkyl ester. Under the catalysis of CuI, a chiral quaternary ammonium salt and a dialkyl amino dithioformate are used for C-S cross coupling for the first time, and dialkyl amino dithiocarbamate alkyl ester is prepared. The target product is further converted andcoupled with brominated aromatic hydrocarbons to obtain high-purity enantiomer chiral thioethers. The synthesis process has the advantages of mild reaction conditions, wide universality, no toxicity or danger, high yield, wide substrate range and the like.
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Paragraph 0010-0016
(2020/02/04)
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- Transition-Metal-Free C(sp3)–S Coupling in Water: Synthesis of Benzyl Dithiocarbamates Using Thiuram Disulfides as an Organosulfur Source
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A simple, highly efficient and environmentally benign method for the synthesis of benzyl dithiocarbamates was reported. Without addition of metal catalyst, a series of 34 benzyl dithiocarbamates were obtained in good to excellent yields by treating benzyl halides with tetraalkylthiuram disulfides in water. The protocol allows easy access to C(sp3)–S bond formation, features the advantages of easy performance, environmental friendliness, good to excellent yields, and good functional tolerance, showing potential value for the preparation of some biologically active compounds.
- Peng, Han-Ying,Dong, Zhi-Bing
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p. 949 - 956
(2018/11/27)
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- An Efficient Synthesis of Benzyl Dithiocarbamates by Base-Promoted Cross-Coupling Reactions of Benzyl Chlorides with Tetraalkylthiuram Disulfides at Room Temperature
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A straightforward, mild and efficient protocol for the synthesis of benzyl dithiocarbamates from benzyl chlorides and tetraalkylthiuram disulfides is presented. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and enables construction of various dithiocarbamate derivatives from readily available starting materials.
- Wu, Zhiyong,Lai, Miao,Zhang, Siyuan,Zhong, Xianyun,Song, Hao,Zhao, Mingqin
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supporting information
p. 7033 - 7036
(2019/01/04)
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- A novel electrocatalytic nanocomposite of reduced graphene oxide/silver nanocube hybrid decorated imprinted polymer for ultra-trace sensing of temozolomide
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A new nanocomposite of reduced graphene oxide/silver nanocube hybrid decorated molecularly imprinted polymer at the surface of a screen-printed carbon electrode was developed for the electroanalysis of an anticancerous drug, temozolomide, at the ultra-trace level. For this, a hybrid of reduced graphene oxide/silver nanocubes was successfully obtained through the simultaneous reduction of Ag+ and graphene oxide via simple one-pot green synthesis. Among the various shapes of nanomaterials used in imprinted polymer synthesis, silver nanocubes, as evident from SEM, TEM and, X-ray diffraction methods, have been found to render high surface to volume ratios and a higher electrocatalytic activity. Herein, the synergistic electrocatalytic effect of reduced graphene oxide and silver nanocubes was utilized for decreasing the analyte oxidation overpotential, without any interfacial barrier in between the imprinted film and the electrode surface, owing to the porous texture of the coating. Consequently, approximately 3-fold differential pulse anodic stripping current and ～5-fold electron transfer rate kinetics were obtained on the reduced graphene oxide/silver nanocube hybrid compared with the simple graphene oxide decorated sensor. The covalent Ag-S links, in between the imprinted film and the silver nanocube decorated screen-printed carbon electrode, were crucial for imparting higher stability to the coating of the film. A perfect linearity in the current-concentration profile was observed, in the range 1.09-144.21 ng mL-1, with the detection limits of 0.16 (aqueous), 0.24 (blood plasma), 0.31 (pharmaceutics), and 0.42 (urine) ng mL-1 (S/N = 3). The proposed sensor was found to be useful in aqueous and real samples (human blood plasma, human urine, and pharmaceutics), without any matrix effect, cross-reactivity, or false-positives.
- Pathak, Purnendu Kumar,Kumar, Anil,Prasad, Bhim Bali
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p. 13486 - 13496
(2018/08/21)
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- Direct conversion of methylarenes into dithiocarbamates, thioamides and benzyl esters
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A new strategy for the synthesis of a variety of dithiocarbamates and thioamides has been developed employing inexpensive and readily available methylarenes under metal-free and solvent-free conditions. The approach offers a one-pot procedure and has also been extended to the synthesis of a diverse range of benzyl esters.
- Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
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p. 3887 - 3892
(2014/06/09)
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- An efficient synthesis of dithiocarbamates under ultrasound irradiation in water
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Multicomponent reactions with ultrasonic activation have been used as a simple, rapid, atom economic, and green method for the synthesis of dithiocarbamate derivatives in water. The one-pot, three-component condensation of primary and secondary amines with carbon disulfide and unsaturated carbonyl compounds or alkyl halides under ultrasonic irradiation was developed as a green and fast protocol for the rapid high-yielding preparation of dithio-carbamates in water.
- Azizi, Najmadin,Gholibeglo, Elahm,Nayeri, Sanaz Dehghan
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experimental part
p. 1171 - 1174
(2012/09/25)
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- Exploring the structural requirements for inhibition of the ubiquitin E3 ligase breast cancer associated protein 2 (BCA2) as a treatment for breast cancer
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The zinc-ejecting aldehyde dehydrogenase (ALDH) inhibitory drug disulfiram (DSF) was found to be a breast cancer-associated protein 2 (BCA2) inhibitor with potent antitumor activity. We herein describe our work in the synthesis and evaluation of new series of zinc-affinic molecules to explore the structural requirements for selective BCA2-inhibitory antitumor activity. An N(C - S)S - S motif was found to be required, based on selective activity in BCA2-expressing breast cancer cell lines and against recombinant BCA2 protein. Notably, the DSF analogs (3a and 3c) and dithio(peroxo)thioate compounds (5d and 5f) were found to have potent activity (submicromolar IC50) in BCA2 positive MCF-7 and T47D cells but were inactive (IC50 > 10 μM) in BCA2 negative MDA-MB-231 breast cancer cells and the normal breast epithelial cell line MCF10A. Testing in the isogenic BCA2 +ve MDA-MB-231/ER cell line restored antitumor activity for compounds that were inactive in the BCA2 -ve MDA-MB-231 cell line. In contrast, structurally related dithiocarbamates and benzisothiazolones (lacking the disulfide bond) were all inactive. Compounds 5d and 5f were additionally found to lack ALDH-inhibitory activity, suggestive of selective E3 ligase-inhibitory activity and worthy of further development.
- Brahemi, Ghali,Kona, Fathima R.,Fiasella, Annalisa,Buac, Daniela,Soukupová, Jitka,Brancale, Andrea,Burger, Angelika M.,Westwell, Andrew D.
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supporting information; experimental part
p. 2757 - 2765
(2010/08/20)
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- Electrogenerated base-promoted synthesis of dithiocarbamate acid esters and 3-(N-substituted-amino)-2-cyanodithiocrotonates from primary or secondary amines and carbon disulfide
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Electrogenerated cyanomethyl anion promotes the reaction between primary or secondary amines, carbon disulfide, and alkyl or benzyl halide. Secondary amines are converted to alkyl or benzyl dithiocarbamates, whereas primary amines give N-substituted alkyl
- Toumi, Meriem,Raouafi, Noureddine,Boujlel, Khaled,Tapsoba, Issa,Picard, Jean-Paul,Bordeau, Michel
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p. 2477 - 2490
(2008/02/10)
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- Straightforward and highly efficient catalyst-free one-pot synthesis of dithiocarbamates under solvent-free conditions
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A highly efficient and simple synthesis of dithiocarbamates is possible based on the one-pot reaction of amines, CS2, and alkyl halides without using a catalyst under solvent-free conditions. The mild reaction conditions, high yields, and broad scope of the reaction illustrate the good synthetic utility of this method. The reaction is a highly atom-economic process for production of S-alkyl thiocarbamates and successfully can be used in high quantities in the pharmaceutical or agrochemical industries.
- Azizi, Najmedin,Aryanasab, Fezzeh,Saidi, Mohammad R.
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p. 5275 - 5277
(2007/10/03)
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- VECTOR
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The present invention provides a vector which can make nucleic acids to be an aggregate and locate a vector containing a cationic polymer to surround the aggregate so as to protect the nucleic acids from the enzyme. The vector comprises a polymer having branched chain(s). Preferably, 3, 4, or 6 branched chains are bonded to benzene ring. It is preferable that the number of the branched chains is higher. As the branched chain(s), a vinyl-series acrylic polymer is preferable. The vector is synthesized by reacting a dithiocarbamate compound with an acrylamide monomer for the branched chain(s).
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- Thiocarbonylthio compounds (S=C(Z)S-R) in free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization). Effect of the activating Group Z
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Free-radical polymerization in the presence of suitable addition-fragmentation chain transfer agents [S=C(Z)S-R] (RAFT agents) possess the characteristics of a living polymerization (i.e., polymer products can be reactivated for chain extension and/or block synthesis, molecular weights are predetermined by RAFT agent concentration and conversion, narrow polydispersities are possible). Styrene polymerizations (110°C, thermal initiation) were performed for two series of RAFT agents [S=C(Z)S-CH2Ph and S=C(Z)S-C(Me)2CN]. The chain transfer coefficients decrease in the series where Z is Ph > SCH2Ph ～ SMe ～ Me ～ N-pyrrolo ? OC6F5 > N-lactam > OC6H5 > O(alkyl) ? N(alkyl)2 (only the first five in this series provide narrow polydispersity polystyrene ( trithiocarbonates ～ dithioalkanoates > dithiocarbonates (xanthates) > dithiocarbamates. However, electron-withdrawing substituents on Z can enhance the activity of RAFT agents to modify the above order. Thus, substituents that render the oxygen or nitrogen lone pair less available for delocalization with the C=S can substantially enhance the effectiveness of xanthates or dithiocarbamates, respectively. The trend in relative effectiveness of the RAFT agents is rationalized in terms of interaction of Z with the C=S double bond to activate or deactivate that group toward free radical addition. Molecular orbital calculations and the estimated LUMO energies of the RAFT agents can be used in a qualitative manner to predict the effect of the Z substituent on the activity of RAFT agents.
- Chiefari, John,Mayadunne, Roshan T.A.,Moad, Catherine L.,Moad, Graeme,Rizzardo, Ezio,Postma, Almar,Skidmore, Melissa A.,Thang, San H.
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p. 2273 - 2283
(2007/10/03)
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- A one-pot rapid synthesis of dithiocarbamates from alcohols using a polymer supported diethyl dithiocarbamate anion
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A polymer supported diethyl dithiocarbamate anion reacts with primary and secondary alcohols via their tirfluoracetates giving alkylated diethyl dithiocarbamates in good yields.
- Bandgar,Sadavarte,Uppalla
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p. 450 - 451
(2007/10/03)
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