92-84-2Relevant academic research and scientific papers
A highly selective phenothiazine-based fluorescence 'turn-on' indicator based on cyanide-promoted novel protection/deprotection mechanism
Garg, Bhaskar,Ling, Yong-Chien
, p. 8809 - 8812 (2015)
A cyanide anion (CN-)-triggered deprotection of NH-protected phenothiazine, (E)-10-(10H-phenothiazin-3′-yl)propenal, has been discovered as a novel mechanism for the highly selective fluorescence detection of CN- under ambient conditions. The present protocol may pave the way for its broad application in organic synthesis in the near future. This journal is
More than just a GPCR ligand: Structure-based discovery of thioridazine derivatives as Pim-1 kinase inhibitors
Li, Wei,Wan, Xiaobo,Zeng, Fanqi,Xie, Yuting,Wang, Yanli,Zhang, Wei,Li, Li,Huang, Niu
, p. 507 - 511 (2014)
Pim-1 kinase is a serine/threonine kinase which plays an important role in cell proliferation and differentiation. The Pim-1 kinase expression is elevated in leukemia and prostate cancer. Accordingly, we employed a structure-based hierarchical virtual screening approach to identify potential unknown Pim-1 kinase activity for existing drugs. Among the LOPAC library of pharmacologically active compounds, one top-ranked drug molecule thioridazine, a well-known antipsychotic agent which exerted its biological function as a dopamine receptor antagonist, showed low micromolar activity in the Pim-1 enzymatic assay. We determined the co-crystal structure of thioridazine bound with Pim-1 kinase, and defined the key elements of the pharmacophore by analyzing the structure-activity relationship of thioridazine analogues. In addition, we also assessed our pharmacophore by successfully predicting the Pim-1 activity of the selective Akt inhibitor, 10-DEBC. Our discovery of the unknown Pim-1 inhibitory activity of thioridazine and 10-DEBC might provide novel insights into understanding their molecular mechanism of action, and inspire the computation-driven multiple-target drug discovery.
14N/15N isotope effect on the electron transfer process between phenothiazine and its radical cation
Wu, Long-Min,Lue, Jian-Ming,Wen, Xiao-Lin,Jia, Xue-Qing,Liu, You-Cheng,Liu, Zhong-Li
, p. 152 - 158 (1997)
An appreciable equilibrium isotope effect has been observed for electron transfer from phenothiazine (PT) to the radical cation of its 15N-substituted analogue ([15N]PT+?), i.e. equation presented via electron paramagnetic resonance analysis of the mixed radical cations formed from mixing the [15N]phenothiazine radical cation hexachloroantimonate and phenothiazine in acetonitrile (K=0·77±0·10 at 25 °C), and by physical separation of the neutral phenothiazines from the radical cation salts in the equilibrium mixture (K=0·83±0·10 at 25 °C). Infrared and Raman spectra of [14N]- and [15N]phenothiazines and their radical cations were measured to assign the vibrational frequency shifts caused by the heavy-atom substitution and radical cation formation, which gave an estimate of the enthalpy change of 441·7 J mol-1 for the electron transfer process. These results reveal that 15N substitution of phenothiazine decreases appreciably the ionization potential of the molecule, making it easier to lose an electron to form the corresponding radical cation in solution.
Carbon- and SO2-Locked Diarylnitroxides: Quantum Chemical Consideration, Synthesis, and Electrochemistry
Levitskiy, Oleg A.,Dulov, Dmitry A.,Bogdanov, Alexey V.,Magdesieva, Tatiana V.
, p. 6225 - 6231 (2019)
Selection of linkers connecting two phenyl rings as a part of molecular design of diarylnitroxides with increased kinetic stability of redox forms was performed using quantum chemical estimation of the geometry and oxidation potential values. It revealed that introduction of the carbon bridge cannot be considered as efficient “instrument” for structural tuning of the nitroxide properties since altering neither the length of the bridge nor its position results in significant changes in the oxidation potential, in contrast to a heteroatomic bridge, which makes more perturbation in the electronic structure of diarylnitroxide. To support the prediction, new SO2-bridged diarylnitroxide was synthesized and characterized using spectral and electrochemical methods. It is extremely stable in benzene solution, exhibits the maximal anodic potential value achieved for reversibly oxidized nitroxides to date (1.33 V, Ag/AgCl/KCl) and seems promising as cathodic redox active material providing maximal potential gap as compared to the previously reported compounds.
Sugarcane field weeding composition
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Paragraph 0018; 0033; 0042; 0051; 0060; 0069; 0077, (2021/06/26)
The invention discloses a weeding composition for a sugarcane field. The weeding composition is prepared from the following components in percentage by weight: 1-60% of triclopyr, 1-30% of metrazone-dinitrate, 1-50% of a weeding substance, 20-40% of silicon dioxide sol, 1-3% of a surfactant, 5-10% of triethanolamine, 3-10% of vegetable oil and the balance of a carrier. According to the invention, a pesticide application method that various herbicides such as triclopyr, Mesotrione, ametryn, cyanazine and atrazine are mixed together is adopted, so that the prevention and control effect of the herbicide is synergistic; The herbicide controlling spectrum can be greatly expanded, the number of times of pesticide application is reduced, the pesticide effect is improved, the proper period of pesticide application is prolonged, the pesticide damage to crops is reduced, the residual activity of the herbicide is reduced, and the occurrence and development of herbicide resistance of the herbicide are delayed. The silicon dioxide sol containing antioxidant groups is used for coating the weeding components, so that the application is safer, the antioxidant activity of the weeding composition is remarkably improved, and the weeding composition is easier to store.
One-Pot Tandem Access to Phenothiazine Derivatives from Acetanilide and 2-Bromothiophenol via Rhodium-Catalyzed C-H Thiolation and Copper-Catalyzed C-N Amination
Rui, Xiyan,Wang, Chao,Si, Dongjuan,Hui, Xuechao,Li, Keting,Wen, Hongmei,Li, Wei,Liu, Jian
, p. 6622 - 6632 (2021/05/29)
A one-pot and step economic reaction involving Rh(III)-catalyzed C-H thiolation and relay Cu(II)-catalyzed C-N amination of acetanilide and 2-bromothiophenol is reported here, with several valuable phenothiazine products obtained. This synthesis protocol proceeds from easily starting materials, demonstrating high atom economy, broad substrate scope, and good yield. Furthermore, the directing group can be easily eliminated, and chlorpromazine is provided in a large scale; thus this synthesis protocol could be utilized to construct phenothiazine scaffolds.
Phenacyl Phenothiazinium Salt as a New Broad-Wavelength-Absorbing Photoinitiator for Cationic and Free Radical Polymerizations
Liu, Ren,Xu, Dandan,Yagci, Yusuf,Zhang, Yuchao,Zhou, Yufan,Zhu, Yi
supporting information, p. 16917 - 16921 (2021/06/28)
A novel broad-wavelength-absorbing photoinitiator based on phenacyl phenothiazinium hexafluroantimonate (P-PTh) possessing both phenacyl and phenothiazine chromophoric groups was reported. P-PTh absorbs light at UV, Visible and Near-IR region. Photophysical, photochemical, and computational investigations revealed that P-PTh in solution decomposes at all wavelengths by homolytic and heterolytic cleavages and generates cationic and radical species, which could efficiently initiate cationic and free radical polymerizations. It is anticipated that the photoinitiator with such wavelength flexibility may open up new pathways in curing applications of formulations of pigment systems.
Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores
Li, Jinshan,Wang, Jiali,Yang, Jianguo,Yao, Wubing,Zhong, Aiguo
, p. 8086 - 8090 (2020/11/03)
The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.
A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides
Sun, Wanwan,Chen, Xiaobei,Hu, Ying,Geng, Huihui,Jiang, Yuanrui,Zhou, Yuxin,Zhu, Wenjing,Hu, Min,Hu, Haohua,Wang, Xingyi,Wang, Xinli,Zhang, Shilei,Hu, Yanwei
supporting information, (2020/10/05)
A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.
Synthesis of phenoxathiins and phenothiazines by aryne reactions with thiosulfonates
Hosoya, Takamitsu,Kanemoto, Kazuya,Sakata, Yuki,Yoshida, Suguru
supporting information, p. 593 - 596 (2020/05/19)
Novel synthetic methods for phenoxathiins and phenothiazines by aryne reactions are disclosed. We found that phenoxathiins were efficiently prepared by the reaction between aryne intermediates and S-(2-hydroxyaryl) 4-toluenethiosulfo-nates. A synthetic method for phenothiazines was also developed by the reaction of arynes with S-(2-aminoaryl) 4-toluenethiosulfonates.
