- New multidentate ligands for supramolecular coordination chemistry: Double and triple helical complexes of ligands containing pyridyl and thiazolyl donor units
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Four new multidentate N-donor ligands L1-L4 have been prepared which contain a combination of pyridyl and thiazolyl donor units. The syntheses of these ligands are facile and high-yielding, being based on reaction of an α-bromoacetyl unit with a thioamide to form the thiazolyl ring. The extended linear sequence of ortho-linked N-donor heterocycles (four for L1, six for L2; five for L3; and six for L4) is reminiscent of the well-known linear oligopyridines, although these new ligands are much easier to make and have significantly different geometric coordination properties because the presence of the five-membered thiazolyl rings results in natural breaks of the ligand backbone into distinct bidentate or terdentate domains. Thus, the tetradentate ligand L1 partitions into two bidentate domains to give dinuclear triple helicates [M2(L1)3]4+ with six-coordinate first-row transition metal dications (M = Co, Cu, Zn). The hexadentate ligand L2 partitions into two terdentate domains to give dinuclear double helicates [M2(L2)2]4+ with six-coordinate metal ions (M = Cu, Zn). In the double helicate [Cu2(L3)2]4+ the pentadentate ligand L3 only uses its two terminal bidentate binding sites, resulting in four-coordinate Cu(II) centres and a non-coordinated pyridyl residue in the centre of each of the two ligand strands. These pendant pyridyl residues are directed towards each other to give a potentially two-coordinate cavity between the metal ions in the centre of the helicate. Similarly, in the double helicate [Cu2(L4)2]4+ the metal ions are only four-coordinate, with each ligand having its central bipyridyl unit un-coordinated. This results in a potentially four-coordinate cavity between the two metal ions in the centre of the helicate. These easy-to-prepare ligands offer a great deal of scope for the development of multinuclear helicates.
- Rice, Craig R.,Woerl, Stefan,Jeffery, John C.,Paul, Rowena L.,Ward, Michael D.
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Read Online
- Convergent and Practical Synthesis of Fluorescent Triphenylamine Derivatives and Their Localization in Living Cells
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In the search for new fluorescent triphenylamine (TP) derivatives, we studied the influence of the position and substitution of diverse heterocyclic substituents. A library of 10 fluorescent triphenylamines bearing either oxazoles or thiazoles and pyridiniums, substituted at different positions has been developed. The approach is based on a convergent C?H activation reaction between pyridine-oxazoles or pyridine-thiazoles and di-iodo triphenylamine. We showed that the nature and substitution pattern of the 5-membered- (oxazole, thiazole) or 6-membered heterocycle (pyridine) has a strong influence on their fluorescence properties and on their localization in living cells as they stain either the nucleus or mitochondria.
- Auvray, Marie,Franck, Xavier,Gallavardin, Thibault,Leleu, Stéphane,Mahuteau-Betzer, Florence,Mougeot, Romain,Oger, Samuel
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supporting information
(2022/02/09)
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- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
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Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
- Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
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supporting information
p. 3398 - 3402
(2021/06/25)
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- Green preparation method for thioamide
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The invention discloses a green preparation method for thioamide. According to the method, in the presence of an oxidizing agent and an iodine reagent, a cyano-containing heterocyclic ring, an aromatic hydrocarbon compound and elemental sulfur or thiuram react in a reaction solvent to prepare a thioamide compound. The method is also applicable to other compounds containing cyano groups on sp carbon. The method has the advantages of one-step reaction synthesis, simple operation, mild reaction conditions, broad spectrum, environment friendliness, usage of cheap and easily available raw materials, and good market application prospect. The method solves technical problems in direct thioamidation of cyano-containing pyridine compounds and other cyano-containing heterocyclic and aromatic compounds, and can be used for modification of various cyano-containing pesticides, such as fipronil, ethiprole and the like.
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Paragraph 0053-0061
(2020/05/01)
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- Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives
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The antioxidant, antimalarial, antibacterial, and antitumor activities of thiosemicarbazones have made this class of compounds important for medicinal chemists. In addition, thiosemicarbazones are among the most potent and well-known ribonucleotide reductase inhibitors. In this study, 24 new thiosemicarbazone derivatives were synthesized, and the structures and purity of the compounds were determined by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The IC50 values of these 24 compounds were determined with an assay for ribonucleotide reductase inhibition. Compounds 19, 20, and 24 inhibited ribonucleotide reductase enzyme activity at a higher level than metisazone as standard. The cytotoxic effects of these compounds were measured on the MCF7 (human breast adenocarcinoma) and HEK293 (human embryonic kidney) cell lines. Similarly, compounds 19, 20, and 24 had a selective effect on the MCF7 and HEK293 cell lines, killing more cancer cells than cisplatin as standard. The compounds (especially 19, 20, and 24 as the most active ones) were then subjected to docking experiments to identify the probable interactions between the ligands and the enzyme active site. The complex formation was shown qualitatively. The ADME (absorption, distribution, metabolism, and excretion) properties of the compounds were analyzed using in-silico techniques.
- Ertas, Merve,Sahin, Zafer,Bulbul, Emre F.,Bender, Ceysu,Biltekin, Sevde N.,Berk, Barkin,Yurttas, Leyla,Nalbur, Aysu M.,Celik, Hayati,Demirayak, ?eref
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- A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
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A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well tolerated at room temperature. In addition, the products were easily separated from the IL which could be reused at least five times without considerable loss of its activity and applied in the green, concise synthesis of ethionamide.
- Cao, Xian-Ting,Qiao, Li,Zheng, Hui,Yang, Hui-Yong,Zhang, Peng-Fei
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p. 170 - 175
(2018/01/17)
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- A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
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A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.
- Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
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p. 509 - 517
(2018/03/27)
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- New promising methods of synthesis of pyridinecarbothioamides
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New methods of synthesis of pyridinecarbothioamides from the corresponding cyanopyridines with the use of phosphorus pentasulfide as a thiontion agent were developed. The first method was based on the reaction of cyanopyridine with phosphorus pentasulfide in alcoholic ammonium solution followed by hydrolysis. The method provided the corresponding thioamides in 60-90% yield. The second procedure included the reaction of phosphorus pentasulfide with 4-cyanopyridine in aqueous ammonia solution, which led to the formation of pyridine-4-carbothioamides in quantitative yield.
- Khromova, N. Yu.,Malekin,Kutkin,Kondrat'Ev
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p. 2295 - 2298
(2015/11/24)
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- From liquid to solid-state fluorescence: Tricyclic lactones based on 4-hydroxy-1,3-thiazoles
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This work describes the synthesis of a series of tricyclic lactones based on 4-hydroxy-1,3-thiazoles prepared by the classic Hantzsch synthesis. The tricyclic lactones are more rigid than the parent 4-hydroxythiazoles and are featured not only by fluorescence in solution, but also in the solid state. An extension of the chromophoric system was successfully realized by integration of the benzothiazole substructure, thus resulting in bathochromic shifts of absorption and also fluorescence. The new synthesized lactones additionally show interesting properties in solution, whereby the initial blue fluorescence changes dramatically with a variation of the pH value. Georg Thieme Verlag Stuttgart · New York.
- Calderón Ortiz, Lorena K.,Würfel, Hendryk,T?uscher, Eric,Wei, Dieter,Birckner, Eckhard,G?rls, Helmar,Beckert, Rainer
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p. 126 - 134
(2014/01/06)
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- A new application of rhodanine as a green sulfur transferring agent for a clean functional group interconversion of amide to thioamide using reusable MCM-41 mesoporous silica
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A novel thionation protocol for amide compounds, with the system rhodanine/secondary amine has been discovered. Clean and efficient synthesis of a variety of thioamides can be achieved through this simple and convenient method using MCM-41 mesoporous silica as an acid catalyst. For this purpose we have synthesized MCM-41 silica and characterized by using an array of sophisticated analytical techniques like BET, HR TEM, EDX, XRD, 29Si MAS NMR and FTIR. This reaction is therefore a very neat example of a functional group interconversion.
- Ray, Suman,Bhaumik, Asim,Dutta, Arghya,Butcher, Ray J.,Mukhopadhyay, Chhanda
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p. 2164 - 2170
(2013/05/08)
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- Arylamine-modified thiazoles as donor-acceptor dyes: Quantum chemical evaluation of the charge-transfer process and testing as ligands in ruthenium(II) complexes
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A series of new 4-hydroxy-1,3-thiazole-based chromophores bearing different arylamine components (triarylamines, carbazole, and phenothiazine) as electron donors and azaheterocycle components (pyridine, pyrazine and pyrimidine) as electron-acceptor moieti
- Menzel, Roberto,Kupfer, Stephan,Mede, Ralf,Weiss, Dieter,Goerls, Helmar,Gonzalez, Leticia,Beckert, Rainer
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p. 5231 - 5247
(2012/10/30)
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- Efficient and green protocol for the synthesis of thioamides in C 6 (mim)2Cl2 as a dicationic ionic liquid
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A simple, efficient, facile and eco-friendly process for the synthesis of thioamides from nitriles using 1,6-bis(3methylimidazolium-1-yl)hexane chloride [C6(mim)2Cl2] as a dicationic ionic liquid (DIL) was developed. The ionic liquid was easily separated from the reaction mixture and was recycled at least four times without any loss of its activity.
- Khosropour,Noei,Mirjafari
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experimental part
p. 752 - 758
(2010/11/04)
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- Synthesis and characterization of new 4-hydroxy-1,3-thiazoles
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A series of highly substituted 4-hydroxy-1,3-thiazoles was synthesised in two different ways. Whereas their anions display strong fluorescence in the bathochromic part of the visible spectrum, the emission is shifted hypsochromically upon alkylation reactions. This easy switch between the anion and its derivatives makes them suitable for widespread applications. The thiazoles possess prerequisites for the complexation of metals due to the coexistence of aza-heterocycles and of 1,3-diketone substructures. In addition, the hydroxy group allows further functionalisation reactions, as exemplified by the incorporation of an azide or an acetylene into the product, and by the synthesis of a star-shaped derivative. Georg Thieme Verlag Stuttgart.
- Taeuscher, Eric,Weiss, Dieter,Beckert, Rainer,Goerls, Helmar
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experimental part
p. 1603 - 1608
(2010/06/22)
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- The combination of 4-hydroxythiazoles with azaheterocycles: Efficient bidentate ligands for novel ruthenium complexes
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Herein the syntheses of three novel ligands, in which an azaheterocycle is connected with a thiazole subunit: 4-methoxy-5methyl-2-pyridine-2-yl-1, 3-thiazole (1), 4-methoxy-5-methyl-2-pyrimidine-2-yl-1, 3-thiazole (2) and 4-methoxy-5-phenyl-2-pyridine-2-y
- Menzel, Roberto,Taeuscher, Eric,Weiss, Dieter,Beckert, Rainer,Goerls, Helmar
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experimental part
p. 1380 - 1385
(2011/01/09)
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- A mild and versatile synthesis of thioamides
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Aliphatic and aromatic nitriles react with thioacetic acid in the presence of calcium hydride to give the corresponding thioamides in good to excellent yields. The examples studied include haloaryl nitriles in which the halogen is facile towards SNAr reactions under other conditions. Georg Thieme Verlag Stuttgart.
- Mahammed,Jayashankara,Premsai Rai,Mohana Raju,Arunachalam
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experimental part
p. 2338 - 2340
(2009/12/08)
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- 4-Alkoxycarbonyl-2-(2-pyridyl)thiazoles and their complexes with CuII and CoII. Molecular and crystal structure of copper 4-ethoxycarbonyl-2-(2-pyridyl) thiazole dichloride
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The first synthesis of ethyl 2-(2-pyridyl)thiazole-4-carboxylate (2) and bis[2-(2-pyridylthi-azol-4-ylcarbonyloxy)ethyl] disulfide (4) is described. The complexation of compounds 2 and 4 with CuII, CoII, and NiII chlorides and perchlorates has been studied. Electrochemical behavior of the ligands and complexes obtained has been investigated by cyclic voltammetry and using rotating disk electrode, which allowed us to confirm the possibility for the ligand 4 and its complexes to be adsorbed on the surface of a gold electrode.
- Majouga,Beloglazkina,Frolov,Moiseeva,Zyk
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experimental part
p. 844 - 850
(2010/08/08)
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- TiCl3OTf-[bmim]Br: a novel and efficient catalyst system for chemoselective one-pot synthesis of thioamides from arylaldoximes
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The combination of TiCl3OTf with 1-butyl-3-methylimidazolium bromide is found to be an efficient and novel catalytic system for chemoselective one-pot transformation of arylaldoximes to their corresponding thioamides in high to excellent yields.
- Noei, Jalil,Khosropour, Ahmad R.
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scheme or table
p. 6969 - 6971
(2009/04/07)
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- HIV protease inhibiting compounds
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A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.
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Page/Page column 97
(2010/02/12)
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- HIV protease inhibiting compounds
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A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.
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Page/Page column 129
(2010/02/12)
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- HIV PROTEASE INHIBITING COMPOUNDS
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A compound of the formula (I) is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.
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Page/Page column 158
(2010/02/12)
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- Simple microwave-assisted method for the synthesis of primary thioamides from nitriles
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Primary thioamides are prepared in excellent yield from the corresponding nitrile by treatment with ammonium sulfide in methanol, at room temperature for electron-deficient aromatic nitriles or under microwave irradiation at 80 °C or 130 °C in 15-30 minutes for other aromatic and aliphatic nitriles. This procedure avoids the use of gaseous H2S under high pressure, proceeds in the absence of base and provides thioamides usually without the need for chromatographic purification.
- Bagley, Mark C.,Chapaneri, Krishna,Glover, Christian,Merritt, Eleanor A.
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p. 2615 - 2617
(2007/10/03)
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- From N-substituted thioamides to symmetrical and unsymmetrical 3,4,5-trisubstituted 4H-1,2,4-triazoles: Synthesis and characterisation of new chelating ligands
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An improved protocol for the synthesis of N-substituted pyridine-2-thiocarboxamides under the conditions of the Willgerodt-Kindler reaction, employing a catalytic amount of sodium sulfide nonahydrate, has been developed. Following this protocol, eight thioamides carrying aromatic or aliphatic N-substituents have been prepared in good to excellent yields. Condensation of these thioamides or their S-alkylated congeners with hydrazides in refluxing 1-butanol has afforded eight unfused 3,4,5-trisubstituted 4H-1,2,4-triazoles in good yields, including four examples of the otherwise not easily obtainable 4-alkyl-3,5-diaryl-4H-1,2,4-triazoles. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Klingele, Marco H.,Brooker, Sally
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p. 3422 - 3434
(2007/10/03)
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- SUBSTITUTED THIAZOLE DERIVATIVES BEARING 3-PYRIDYL GROUPS, PROCESS FOR PREPARING THE SAME AND USE THEREOF
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The present invention provides a pharmaceutical composition having a steroid C17,20-lyase inhibitory activity, which is useful as a prophylactic or therapeutic agent of prostatism, tumor such as breast cancer and the like, more particularly, a steroid C17,20-lyase inhibitor containing a compound represented by the formula: wherein A1 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, one of A2 and A3 is a hydrogen atom, a halogen atom, a C1-4 aliphatic hydrocarbon group optionally having substituents or an optionally esterified carboxyl group, the other of A2 and A3 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, and at least one of A1, A2 and A3 is a 3-pyridyl group optionally having substituents, or a salt thereof or a prodrug thereof.
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Page/Page column 61
(2008/06/13)
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- Synthesis of primary thioamides from nitriles and hydrogen sulfide catalyzed by anion-exchange resin
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A new method has been developed for converting nitriles into primary thioamides. Treatment of various nitriles (Table 1, entries 1-12) with gaseous hydrogen sulfide in a mixture of methanol-water or ethanol-water and in the presence of anion-exchange resin (Dowex 1X8, SH- form) at room temperature and ambient pressure gave the corresponding thioamides in 25-96% yield.
- Liboska, Radek,Zyka, Daniel,Bobek, Miroslav
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p. 1649 - 1651
(2007/10/03)
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- Diguanidino and "reversed" diamidino 2,5-diarylfurans as antimicrobial agents
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Dicationic 2,5-bis(4-guanidinophenyl)furans 5a-5f, 2,5-bis[4- (arylimino)aminophenyl]furans 6a-6b and 6e-6k, and 2,5-bis[4-(alkylimino)aminophenyl]furans 6c-6d have been synthesized starting from 2,5-bis[tri-n-butylstannyl]furan. Thermal melting studies w
- Stephens,Tanious,Kim,Wilson,Schell,Perfect,Franzblau,Boykin
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p. 1741 - 1748
(2007/10/03)
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- Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: Analogues of cytotoxic marine bis(indole) alkaloid
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2,4-Bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis(3'-indolyl)pyrazine were synthesized and evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. These compounds demonstrated significant inhibitory effects in the growth of a range of cancer cell lines. 2,4-Bis(3'-indolyl)thiazole displayed selective cytotoxicity against certain leukemia cell lines with GI50 values in the low micromolar range while the substituted derivatives showed a broad spectrum of cytotoxic activity. 3,5-Bis(3'-indolyl)-2(1H)pyrazinone and 3,6- bis[3'-(N-methyl-indolyl)]pyrazine possessed strong inhibitory activity against a wide range of human tumor cell lines. The mechanism of action remained unknown. The results suggested that 2,4-bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis[3'-(N-methyl-indolyl)] pyrazine offer potential as lead compounds for the discovery of anticancer agents. (C) 2000 Elsevier Science Ltd.
- Jiang, Biao,Gu, Xiao-Hui
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p. 363 - 371
(2007/10/03)
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- 28. Novel thiazole-containing complexing agents and luminescence of their europium(III) and terbium(III) chelates
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The synthesis of novel thiazole-containing complexing agents and their luminescence properties with EuIII and TbIII ions are reported. One of these terpyridine analogues was also tested as an EuIII labelling reagent, and its luminescence properties as an antibody conjugate were studied.
- Mukkala, Veli-Matti,Liitti, Paeivi,Hemmilae, Ilkka,Takalo, Harri,Matachescu, Cristina,Kankare, Jouko
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p. 295 - 306
(2007/10/03)
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- A REMARKABLY SIMPLE CONVERSION OF NITRILES TO THIOAMIDES
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Thiolacetic acid and light smoothly convert nitriles to thioamides.
- Gauthier, Jacques Yves,Lebel, Helene
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p. 325 - 326
(2007/10/02)
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- A new method for converting nitriles into primary thioamides by sodium trimethylsilanethiolate
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A new method was developed for converting nitriles into primary thioamides. Treatment of various nitriles 1 with 1.5-2.5 equivalents of sodium trimethylsilyl sulfide (sodium trimethylsilanethiolate) in 1,3-dimethyl-2-imidazolidinone at 20-35°C for 4-30 hours gave the corresponding thioamides 2 in 27-80% yield.
- Lin,Ku,Shiao
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p. 1219 - 1220
(2007/10/02)
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