5346-38-3Relevant academic research and scientific papers
New multidentate ligands for supramolecular coordination chemistry: Double and triple helical complexes of ligands containing pyridyl and thiazolyl donor units
Rice, Craig R.,Woerl, Stefan,Jeffery, John C.,Paul, Rowena L.,Ward, Michael D.
, p. 550 - 559 (2001)
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.
Convergent and Practical Synthesis of Fluorescent Triphenylamine Derivatives and Their Localization in Living Cells
Auvray, Marie,Franck, Xavier,Gallavardin, Thibault,Leleu, Stéphane,Mahuteau-Betzer, Florence,Mougeot, Romain,Oger, Samuel
supporting information, (2022/02/09)
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.
Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
supporting information, p. 3398 - 3402 (2021/06/25)
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.
Green preparation method for thioamide
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Paragraph 0053-0061, (2020/05/01)
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.
Potent ribonucleotide reductase inhibitors: Thiazole-containing thiosemicarbazone derivatives
Ertas, Merve,Sahin, Zafer,Bulbul, Emre F.,Bender, Ceysu,Biltekin, Sevde N.,Berk, Barkin,Yurttas, Leyla,Nalbur, Aysu M.,Celik, Hayati,Demirayak, ?eref
, (2019/11/03)
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.
A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
Cao, Xian-Ting,Qiao, Li,Zheng, Hui,Yang, Hui-Yong,Zhang, Peng-Fei
, p. 170 - 175 (2018/01/17)
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.
A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
, p. 509 - 517 (2018/03/27)
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.
New promising methods of synthesis of pyridinecarbothioamides
Khromova, N. Yu.,Malekin,Kutkin,Kondrat'Ev
, p. 2295 - 2298 (2015/11/24)
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.
From liquid to solid-state fluorescence: Tricyclic lactones based on 4-hydroxy-1,3-thiazoles
Calderón Ortiz, Lorena K.,Würfel, Hendryk,T?uscher, Eric,Wei, Dieter,Birckner, Eckhard,G?rls, Helmar,Beckert, Rainer
, p. 126 - 134 (2014/01/06)
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.
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
Ray, Suman,Bhaumik, Asim,Dutta, Arghya,Butcher, Ray J.,Mukhopadhyay, Chhanda
, p. 2164 - 2170 (2013/05/08)
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.
