- Synthesis of 2,6-dicarbethoxy-3,5-diaryltetrahydro-1,4-thiazine-1,1-dioxide derivatives as potent anticonvulsant agents
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Abstract An efficient synthesis of 2,6-dicarbethoxy-3,5-diaryltetrahydro-1,4-thiazine-1,1-dioxide derivatives has been achieved under aqueous medium for the first time in good to excellent yields. All the synthesized compounds were tested for anticonvulsant activity using the maximal electroshock (MES), subcutaneous pentylenetetrazole (scPTZ) screens, which are the most broadly employed seizure models for early identification of candidate anticonvulsants. Their neurotoxicity was determined applying the rotarod test. Seven compounds 4a, 4d, 4f, 4h, 4o, 4p and 4q showed promising anticonvulsant activities in both models employed for anticonvulsant evaluation. The most active compound 4d showed the MES-induced seizures with ED50 value of 10.2 mg/kg and TD50 value of 288.6 mg/kg after intraperitoneal injection to mice, which provided compound 4d with a protective index (TD50/ED50) of 28.3 in the MES test.
- Edayadulla, Naushad,Ramesh, Penugonda
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- Polymer material monomer 3, 4 - ethylene dioxy thiophene preparation method
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The invention relates to a method for preparing polymer monomer 3,4-ethylenedioxythiophene. The method includes firstly dissolving ethyl chloroacetate and sodium sulphide in acetone to react to obtain diethyl thioglycolate; secondly, dissolving the diethyl thioglycolate to ethanol, adding sodium ethoxide and diethyl oxalate into the ethanol, heating and reflowing to obtain ethanol solution of 2,5-dioctyl phthalate ethyl ester-3,4-thiophene glycol sodium; thirdly, adding dichloroethane and tetrabutylammonium bromide into the ethanol solution of the 2,5-dioctyl phthalate ethyl ester-3,4-thiophene glycol sodium, heating and reflowing to obtain 3,4-ethylenedioxy-2,5-dioctyl phthalate ethyl ester thiophene; fourthly, dissolving the 3,4-ethylenedioxy-2,5-dioctyl phthalate ethyl ester thiophene in mixed solvent, adding sodium chloride, heating and reacting, and finally reducing pressure and rectifying. The method for preparing polymer monomer 3,4-ethylenedioxythiophene is few in procedures, low in cost, safe and reliable in technique, simple and fast in post-treatment method, and products are high in yield and purity.
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Paragraph 0021; 0080-0082
(2017/08/26)
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- Preparation method of 3,4-ethylene dioxy thiophene
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The invention relates to a preparation method of organic matter, in particular to a preparation method of 3,4-ethylene dioxy thiophene.With chloracetate as the initial raw material, 3,4-ethylene dioxy thiophene is preparated through vulcanization reaction, condensation, etherification, saponification and decarboxylic reaction.The method is easy to operate, low in cost, safe, environmentally friendly, high and stable in product yield, good in product color and luster, simple in process during reaction, not strict in reaction condition and quite suitable for industrial production.
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Paragraph 0015
(2016/12/01)
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- Aminothiophene sulfonic acid ester
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PROBLEM TO BE SOLVED: To provide 3,4-disubstituted thiophene sulfonate usable as a monomer for a conductive polymer, and not having carboxylate on 2,5-positions, and to provide a method for producing the same.SOLUTION: This thiophene sulfonate is represented by general formula (1). The thiophene sulfonate is obtained, for example, by decarboxylation of 3,4-dihydroxy-2,5-dicarboxylic acid thiophene in a basic inert solvent, followed by reaction with sulfonyl chlorides in the presence of a tertiary alkylamine catalyst. (In the formula, Rand Reach independently represent a 1-8C alkyl, phenyl or tolyl).
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Paragraph 0058 - 0059
(2018/02/28)
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- Preparation of an EDOT-based polymer: Optoelectronic properties and electrochromic device application
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Here we present the synthesis, characterization and electropolymerization of a new EDOT-based monomer; 5,10-dihydrobenzo[f]thieno[3,4-b][1,4]dioxocine (DTD). Electrochemical polymerization of DTD was performed potentiostatically by using dichloromethane (DCM) as solvent and tetrabutylammonium hexafluorophosphate (TBPF6) as supporting electrolyte. Homopolymer [P(DTD)] films and copolymer [P(DTD-co-TPA)] films of DTD prepared by using 4-(2,5-di(thiophen-2-yl)-1H-pyrrole-1-yl)butane-1-amine (TPA) were characterized via CV and UV-vis spectroscopy. Spectroelectrochemical analysis of P(DTD) revealed electronic transitions at 585 nm (π-π transition) with an electronic band gap of 1.69 eV. Electrochromic studies revealed that P(DTD) has competitive properties to EDOT. Furthermore, a dual-type complementary colored polymer electrochromic device based on P(DTD) and P(TPA) was constructed in sandwich configuration. Spectroelectrochemical studies revealed that the oxidized state of the device shows a blue color whereas it is yellow in the reduced state. The maximum contrast (Δ%T) and switching time of the device were measured as 25.5% and 0.5 s for 385 nm and 21% and 1.0 s for 550 nm.
- Soganci, Tugba,Kurtay, Gülbin,Ak, Metin,Güllü, Mustafa
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p. 2630 - 2639
(2015/02/05)
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- Preparation method of 3,4-ethylenedioxythiophene
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A method of preparing 3,4-ethylenedioxythiophene is provided. The preparation is performed by microwave heating to greatly increase the yield and decrease the reaction time, energy consumption, solvent usage, and environmental damage.
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Paragraph 0062-0068
(2013/03/26)
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- An improved procedure for the synthesis of 3,4-ethylenedioxythiophene
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An improved procedure for the synthesis of 3,4-ethylenedioxythiophene is reported starting from ethyl chloroacetate. Reaction with sodium sulfide gave diethyl thiodiglycolate which was then reacted with diethyl oxalate, and then 1,2-dibromoethane to give 2,5-dicarbethoxy-3,4-ethylenedioxythiophene. Hydrolysis, and decarboxylation gave 3,4-ethylenedioxythiophene in 16% overall yield. The structures of the key intermediates in synthetic routes were confirmed, and every step was optimised, to give a procedure suitable for large-scale industrial production.
- Zhang, Hua,Qian, Chao,Chen, Xin-Zhi
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experimental part
p. 339 - 340
(2011/10/02)
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- L-proline-catalyzed three-component domino [3+2+1] annulation for the regio- and diastereoselective synthesis of highly substituted thienothiopyrans containing three or four stereocenters
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(Chemical Equation Presented) L-Proline-catalyzed three-component reactions of ethyl 2-[(2-oxo-2-arylethyl)sulfonyl]acetate or ethyl 2-[(2-ethoxy-2- oxoethyl)sulfonyl]acetate, aromatic aldehydes, and 5-aryltetrahydro-3- thiophenone furnished a variety of highly substituted thieno[3,2-c]thiopyran derivatives. This facile transformation presumably occurs via a one-pot domino sequence of enamine formation/aldol condensation/Michael addition/6-exo-trig cyclization/elimination and involves the creation in a single operation of three C-C bonds and the generation of three new stereocenters with complete diastereoselectivity in all cases and a fourth one in ca. 7:3 diastereomeric ratio when starting from a 5-substituted tetrahydro-3-thiophenone derivative.
- Indumathi, Sethuraman,Perumal, Subbu,Menendez, J. Carlos
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supporting information; experimental part
p. 472 - 475
(2010/03/25)
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- PROCESS FOR PREPARING DIALKYL THIODIGLYCOLATES
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A process is described for preparing alkyl thiodiglycolates of the general formula (I) [in-line-formulae]R—OOC—CH2-S—CH2-COO—R ??(I)[/in-line-formulae] where R is a radical of branched or unbranched C1 to C10-alkyl, characterized in that an alkyl haloacetate of the general formula (II) [in-line-formulae]X—CH2-COO—R ??(II)[/in-line-formulae] where X is a chlorine or bromine atom and R is as defined for compounds of the formula (I) is reacted with an aqueous solution of alkali metal sulphide or alkali metal hydrogensulphide in the presence of an aqueous pH buffer solution in the pH range between 5 and 8, optionally in the presence of a phase transfer catalyst.
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Page/Page column 3
(2009/07/10)
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- Synthesis and anticonvulsant activity of some new bishydrazones derived from 3,4-dipropyloxythiophene
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A series of new 3,4-dipropyloxy-N2,N5-bis(substituted)thiophene-2,5-dicarbohydrazides (4-30) were synthesized from ethyl thiodiglycolate and diethyloxalate through multistep reactions. Following Dieckmann-Komppa reaction, the required precursor 3,4-dihydroxythiophene-2,5-diester (1) was prepared. This was derivatized with propyl bromide and further converted to corresponding hydrazide (3), which was finally transformed to targeted hydrazones (4-30) by conventional methods. The newly synthesized compounds were characterized using FT-IR, 1H and 13C NMR, EI-MS and elemental analyses. The anticonvulsant activity of all the title compounds was investigated against maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scMET) models and their neurotoxicity was also evaluated. Some of the selected compounds were subjected to 6 Hz test in order to evaluate their uncover activities. Compound 3,4-dipropyloxy-N2,N5-bis[1-(2-thienyl)ethylidene]thiophene-2,5-dicarbohydrazide (15) has emerged as a lead in this series with less neurotoxicity.
- Kulandasamy, Ravi,Adhikari, Airody Vasudeva,Stables, James P.
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experimental part
p. 3672 - 3679
(2009/11/30)
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- Prussian blue nanoparticles protected by the water-soluble π-conjugated polymer PEDOT-S: Synthesis and multiple-color pH-sensing with a redox reaction
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Prussian blue nanoparticles (PB NPs), stabilized for the first time by the π-conjugated polymer poly(4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2yl-methoxy- 1-butanesulfonic acid, potassium salt) (PEDOT-S), demonstrated a novel multiple-color pH-sensing function with a redox reaction based on the electronic interaction between the PB nano-core and the PEDOT-S shell. The Royal Society of Chemistry 2009.
- Yamada, Mami,Ohnishi, Naoto,Watanabe, Makoto,Hino, Yasuko
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supporting information; scheme or table
p. 7203 - 7205
(2010/03/25)
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- CARBOXYLIC ACID-MODIFIED EDOT FOR BIOCONJUGATION
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An electroconductive carboxylic acid functionalized monomer corresponding to Formula (I), wherein A represents a hydrogen or a carboxyl group. Polymerized monomers of Formula (I) conjugated with a biomolecule result in conjugated PEDOT polymers of Formula (III) wherein A is a hydrogen or a carboxylic acid group and B is a biomolecule selected from the group consisting of a peptide, a protein, a lipid, a carbohydrate and a polynucleotide. The biomolecule conjugated polymers can be disposed onto an electrically conductive substrate wherein the substrate has a first layer of PEDOT polymerized on a surface of the substrate and a second layer of biomolecule conjugated PEDOT polymer of Formula (III) polymerized on the first layer of PEDOT. The first and second layers form a charge transport material in electrical communication with the conductive substrate. The electrically conductive substrate further comprises a dopant.
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Page/Page column 7-9
(2008/12/07)
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- DERIVATIZED 3,4-ALKYLENEDIOXYTHIOPHENE MONOMERS, METHODS OF MAKING THEM, AND USE THEREOF
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The present invention relates to methods of making derivatized 3,4-alkylenedioxythiophene monomers and methods of using the 3,4-alkylenedioxythiophene monomers.
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Page/Page column 21-22
(2008/06/13)
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- The first direct experimental comparison between the hugely contrasting properties of PEDOT and the all-sulfur analogue PEDTT by analogy with well-defined EDTT-EDOT copolymers
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The structures of poly(3,4-ethylenedioxythiophene) (PEDOT) and poly(3,4-ethylenedithiathiophene) (PEDTT) vary only in the substituent chalcogen atoms, yet the electronic properties of the materials are surprisingly dissimilar. The difference in electronic band gaps is approximately 0.8 eV and the polymers behave very differently upon p-doping. Two new terthiophenes have been synthesised using Negishi coupling methods. The X-ray crystal structures of EDOT-EDTT-EDOT (OSO) and EDTT-EDOT-EDTT (SOS) show strong intramolecular chalcogen-chalcogen contacts which are responsible for persistent conformers in solution and solid state, although significant interchain interactions should also influence the properties of the materials. SOS and OSO can be polymerised by electrochemical oxidation to give the corresponding, well-defined poly(terthiophenes) PSOS and POSO. Spectroelectrochemical studies on all four polymers reveal strong similarities between PEDTT and PSOS, and between PEDOT and POSO. Together with independent electrochemical and absorption studies, the results indicate that the unique properties of PEDOT are influenced more by conformational effects (intrachain S...O contacts) than substituent effects. The Royal Society of Chemistry 2005.
- Spencer, Howard J.,Skabara, Peter J.,Giles, Mark,McCulloch, Iain,Coles, Simon J.,Hursthouse, Michael B.
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p. 4783 - 4792
(2007/10/03)
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- Synthesis of 3,4-diphenyl-substituted poly(thienylene vinylene), low-band-gap polymers via the dithiocarbamate route
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It has been demonstrated that the dithiocarbamate precursor route is a suitable pathway towards poly(thienylene vinylene) (PTV)-type low-band-gap polymers. Two particular dithiocarbamate precursor polymers and the corresponding conjugated polymers, poly(3,4-diphenyl-2,5-thienylene vinylene) and poly(3,4-bis(4-butylphenyl)-2,5-thienylene vinylene), have been studied. The introduction of butyl side chains in the latter leads to excellent solubility in common organic solvents. Both polymers have been prepared in a straightforward manner and in good yield. The thermal conversion of the precursor polymers into the conjugated structure was studied with in situ FT-IR and UV-vis spectroscopy. Also, with the latter technique, the band gap was determined and the thermochromic effect was studied and compared with the unsubstituted PTV. The HOMO and LUMO levels of the polymers were determined from UV-vis and electrochemical measurements.
- Henckens,Colladet,Fourier,Cleij,Lutsen,Gelan,Vanderzande
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- Synthesis and polymerization of new monomers derived from 3,4- ethylenedioxythiophene
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We report here the results of the synthesis of soluble polymers derived from 3,4-ethylenedioxythiophene. Starting from a 3,4-ethylenedioxythiophene monomer functionalized by an hydroxymethyl group, we synthesized several monomers bearing different side groups. The influence of alkyl chain length of side groups was studied in order to improve the solubility of the resulting polymer obtained by chemical oxydation. The optical properties of some chemically polymerized materials are also reported.
- Schottland,Stephan,Le Gall,Chevrot
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p. 1258 - 1261
(2007/10/03)
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- Highly Selective Sulfur Transfer Reaction in the Solid State
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Benzyltriethylammonium tetrathiomolybdate 1 reacts readily with benzyl halides, alkyl iodides and acyl halides in the solid state to give the corresponding disulfides in good yields and with remarkable selectivity.
- Ramesha, A. R.,Chandresekaran, Srinivasan
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p. 767 - 768
(2007/10/02)
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- Enzymatic Hydrolyses of the ?-Symmetric Dicarboxylic Diesters Bearing a Sulfinyl Group as the Prochiral Center
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Enzymatic hydrolyses of the ?-symmetric dicarboxylic diesters bearing a sulfinyl group as the prochiral center were examined by employing porcine liver esterase and porcine pancreatic lipase.Eventually, their chiral half esters were elaborately obtained as the corresponding chiral phenacyl esters.The stereochemistry of the chiral half esters was determined by the X-ray analysis and their chemical correlations.
- Tamai, Satoshi,Miyauchi, Satoru,Morizane, Chikako,Miyagi, Kaname,Shimizu, Hisashi,et al.
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p. 2381 - 2384
(2007/10/02)
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- BIS(BROMOMAGNESIUM) SULFIDE - A REAGENT FOR THE SYNTHESIS OF DIORGANIC SULFIDES
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Bis(bromomagnesium) sulfide was obtained by the reaction of ethylmagnesium bromide with hydrogen sulfide. In reaction with electrophilic reagents in THF or diethyl ether it gives good yields of symmetrical sulfides with a high degree of purity.
- Nedugov, A. N.,Pavlova, N. N.
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p. 1103 - 1104
(2007/10/02)
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- Benzyltriethylammonium tetrathiomolybdate: An improved sulfur transfer reagent for the synthesis of disulfides
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Benzyltriethylammonium tetrathiomolybdate has been found to be a superior reagent for the conversion of alkyl halides to the corresponding disulfides in chloroform at room temperature.
- Ramesha,Chandrasekaran
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p. 3277 - 3284
(2007/10/02)
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- Synthesis of a few 2,4-dihydro-3-benzo- and naphthothiepin-1,5-diones
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2,4-Dihydro-3-benzothiepin-1,5-diones (3a,b and c) and 2,4-dihydronaphthothiepin-1,5-dione (3d) have been synthesised by acylation of the aromatic hydrocarbons (2a,b,c and d) with diethyl thiodiacetate (1), prepared by condensation of ethyl chloroacetate and sodium sulphide.Reduction of the diones (3) through hydrazones affords the corresponding thiepins.
- Singh, Sunil Kumar,Mumtazuddin, Syed,Nizamuddin, Syed
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p. 589 - 591
(2007/10/02)
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- Esters of Thiodiglycollic and Thiodipropionic Acids and 2,5-Dicarboxy-3,4-dihydroxythiophene as Potential Slow Acting Anticancer Agents
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A series of esters of thiodiglycollic and thiodipropionic acids and 2,5-dicarboxy-3,4-dihydroxythiophene have been synthesised with a view to testing their anticancer properties.The esters, as against parent acids are expected to have a prolonged effect.
- Kumar, Anil,Tilak, B. D.
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p. 880 - 882
(2007/10/02)
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