102-08-9Relevant articles and documents
Copper-Catalyzed Double Thiolation to Access Sulfur-Bridged Imidazopyridines with Isothiocyanate
Tian, Lu-Lu,Lu, Shuai,Zhang, Zhe-Hua,Huang, En-Ling,Yan, Hua-Ting,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping
, p. 5213 - 5221 (2019)
A copper(I)-catalyzed sulfur-bridged dimerization of imidazopyridines has been developed using isothiocyanate as the sulfur source. This method enables a switchable synthesis of bis(imidazo[1,2-a]pyridin-3-yl)sulfanes or bis(2-(imidazo[1,2-a]pyridin-2-yl)phenyl)sulfanes in the presence of 4-dimethylaminopyridine (DMAP) or K2CO3 when different imidazopyridines were employed. Under optimized conditions, a variety of sulfur-bridged imidazopyridines were obtained in good yields. Moreover, thiourea was proved to be the key intermediate under catalytic system A.
Synthesis and characterisation of [(en)2Co]3+ complexes coordinated by substituted thiourea ligands
Roecker, Lee,Aiyegbo, Mohammed,Al-Haddad, Aladdin,Fletcher, Emily,Kc, Ravi,Hurst, Jason,Lane, Timothy,Larsen, Ryan,Noinaj, Nicholas,Teh, Say Lee,Wade, Samuel K.,Parkin, Sean
, p. 944 - 951 (2013)
Substituted thiourea ligands bind in a bidentate manner forming a four-membered ring through the sulfur atom and a deprotonated thiourea nitrogen atom when reacted with [(en)2Co(OSO2CF3)2]+ in tetramethylene sulfone. Reaction of unsymmetrical ligands results in the formation of coordination isomers, some of which can be separated by column chromatography using Sephadex SPC-25. Coordination isomers are easily distinguishable based on visible and 1H NMR spectroscopy . Twelve para-substituted and one meta-substituted ligands were studied: N,N′-dibenzylthiourea (1a); N-(R)phenyl-N′-benzylthiourea R≤H (2a), NO2 (2b), CH3 (2c); N-(R)phenyl-N′-(R′)phenylthiourea R, R′: H, H (3a), H, CH3 (3b), OCH3, NO2 (3c), CH3, NO2 (3d); N-methyl-N′-(R)phenylthiourea R≤H (4a), CH3 (4b), OCH3 (4c), NO2 (4d), 3-CH3 (4e). The solid state structure (X-ray) of one isomer of Co-4a as its perchlorate salt confirms the coordination mode suggested by 1H NMR spectroscopy and shows that the Co-N bond trans to the coordinated thiourea sulfur induces a structural trans effect of 0.019A.
Rapid synthesis of a 13C6-benzothiazolium salt from 13C6-aniline
Galliford, Chris V.,Voronin, Kimberly,Hesk, David,Koharski, David,McNamara, Paul
, p. 229 - 232 (2011)
13C6-labeled aniline was used as a starting material for the facile synthesis of 13C6-benzothiazolium salt (1). Copyright
Coupling of single droplet micro-extraction with desorption electrospray ionization-mass spectrometry
Sun, Xiaobo,Miao, Zhixin,Yuan, Zongqian,Harrington, Peter De B.,Colla, Jennifer,Chen, Hao
, p. 102 - 108 (2011)
Single droplet micro-extraction (SDME) is a powerful preconcentration and purification technique for trace chemical analysis, but the detection of the resulting single droplet extract is often time-consuming with traditional detection methods such as GC/MS or LC/MS. In this study, desorption electrospray ionization-mass spectrometry (DESI-MS) was coupled with SDME to serve as a fast detection method for the first time, demonstrated by the trace analysis of methamphetamine (MA) in aqueous solution and the detection of an organic reaction product from an ionic liquid (IL). In the former application, three-phase liquid SDME was conducted to enrich MA in aqueous solution to an organic solvent and then to back-extract the analyte to a single aqueous droplet. Subsequent DESI-MS analysis can be performed either to a single droplet or multiple droplets in a row. The average enrichment factor obtained for MA was 390-fold. In the latter case, two-phase liquid SDME was conducted to directly extract the product of an organic reaction performed in a room temperature ionic liquid (i.e., the nucleophilic addition of aniline to phenyl isothiocyanate to form N,N′-diphenylthiourea in 1-butyl-3-methyl- imidazolium tetrafluoroborate). The ionization of the resulting droplet extract by DESI allows one to directly examine the reaction product without interference from the ionic liquid. Such an analysis uses a few microliters of an organic solvent, achieving green chemistry. This combined SDME/DESI-MS method is characterized with high preconcentration efficiency, high throughput capability and minimizing organic solvent waste.
Barbiturate squaraine dyes as fluorescent probes for serum albumins detection
Almeida, Paulo,Boto, Renato E. F.,Gomes, Vanessa S. D.,Gon?alves, Helena M. R.,Reis, Lucinda V.
, (2020)
Three indolenine-based barbiturate squaraine dyes were synthesized, characterized and subjected to photophysical studies, including their affinity with human serum albumin and bovine serum albumin as protein models in phosphate buffer solution. All dyes successfully interact with both proteins with high affinity binding constants. It was found that dyes with hydrophobic substituents had superior binding constants with both proteins. The fluorescence intensity of all dyes increased in the presence of both proteins which allowed the determination of detection and quantifications limits in the tens of nanomolar, using a protein concentration of 0–3.5 μM. Concerning to the study on the binding sites of the synthesized dyes using the warfarin and ibuprofen markers, the results of this study suggest that, one dye binds to both BSA binding sites while the two others dyes binds only to site I, and that all three dyes bind to both HSA binding sites.
Structural requirement of phenylthiourea analogs for their inhibitory activity of melanogenesis and tyrosinase
Thanigaimalai, Pillaiyar,Lee, Ki-Cheul,Sharma, Vinay K.,Joo, Cheonik,Cho, Won-Jea,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
, p. 6824 - 6828 (2011)
Effect of a series of 1-phenylthioureas 1a-k and 1,3-disubstituted thioureas 2a-k were evaluated against melanin formation in melanoma B16 cell line and mushroom tyrosinase. Inhibitory activity of tyrosinase of 1-phenylthioureas 1a-k is parallel to their melanogenic inhibition. Thus, the melanogenic inhibition in melanoma B16 cells of 1-phenylthioureas could be the result of inhibition of tyrosinase. However, 1,3-diaryl or 1-phenyl-3- alkylthioureas, 2a-k, appears as melanogenic inhibitor without inhibition of tyrosinase. The molecular docking study of 1e and 2b to binding pocket of tyrosinase provided convincing explanation regarding the necessity of direct connection of planar phenyl to thiourea unit without N′-substitution of phenylthioureas 1 as tyrosinase inhibitor and 2 as non-tyrosinase inhibitor.
A CONVENIENT METHOD FOR THE PREPARATION OF N,N'-DISUBSTITUTED THIOUREAS USING 2-CHLOROPYRIDINIUM SALT, SODIUM TRITHIOCARBONATE AND AMINES
Takikawa, Yuji,Inoue, Noriyuki,Sato, Ryu,Takizawa, Saburo
, p. 641 - 642 (1982)
N,N'-Disubstituted thioureas were prepared in high yields by treating 2-chloropyridinium salt with sodium trithiocarbonate and subsequently adding amines.
Naphthyridine derivatives as a model system for potential lithium-sulfur energy-storage applications
Resch, Sebastian,Schneider, Anna-Rebekka,Beichler, Ronja,Spera, Marcelle B. M.,Fanous, Jean,Schollmeyer, Dieter,Waldvogel, Siegfried R.
, p. 933 - 937 (2015)
Naphthyridines have been identified as structural elements in sulfurized polyacrylonitrile, which is a common electrode material in lithium-sulfur batteries. Some dibenzonaphthyridine derivatives with a fused dithiolo moiety were prepared as model compounds for battery studies. These heterocyclic systems were prepared via the corresponding diphenyldicarbamide intermediate. Followed by naphthyridione formation, stepwise installation of the dithiolane subunit occurred in a straightforward manner. In the solid state, the heteroaromatic system is completely planar and was thoroughly characterized. Initial battery cycling tests indicated a potential use of such structural motifs in sulfur-lithium systems.
A synthetic route to novel 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)(thio)barbiturates
Serrano, Jo?o L.,Cavalheiro, Eunice,Barroso, Sónia,Rom?o, Maria J.,Silvestre, Samuel,Almeida, Paulo
, p. 990 - 995 (2017)
2,1-Benzisoxazoles, also called anthranils, are one of the two types of aromatic bicyclic heterocycles having a benzene ring fused with an isoxazole, which are particularly recognized as valuable intermediates in organic synthesis. Nevertheless several methods can be found in the literature to prepare 2,1-benzisoxazoles, we herein report a new, efficient, simple, mild, and alternative procedure to prepare 3-substituted-2,1-benzisoxazoles from 5-(2-nitrobenzylidene)barbiturates in moderate to good yields (51–82%). All the novel benzisoxazoles showed spectral data fully consistent with the assigned structures, which were unequivocally confirmed by single crystal X-ray analysis. A possible mechanism of the reaction is proposed. In addition, a screening of the bioactivity of these benzisoxazoles as xanthine oxidase inhibitors, antioxidants, and cytotoxic compounds was performed. The benzisoxazole formed from barbituric acid revealed moderate xanthine oxidase inhibitory effects (IC50 = 22.10 μM).
One-pot synthesis of highly functionalized benzo [1,3] thiazine from isocyanides, aniline, and heterocumulene via Cu-catalyzed intramolecular C-H activation reactions
Dastjerdi, Hossein F.,Nematpour, Manijeh,Rezaee, Elham,Jahani, Mehdi,Tabatabai, Sayyed A.
, p. 1537 - 1541 (2019)
A one-pot synthesis of functionalized benzo thiazine derivatives via a Cu-catalyzed, multicomponent reaction of isocyanides, aniline, and heterocumulenes in acetonitrile at room temperature was developed. Transition metal-catalyzed activation of C-H bonds
