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Phenothiazinimides: Atom-Efficient Electrophilic Amination Reagents

Phenothiazinimides, a fairly unknown class of imines, were prepared and found to be very reactive as ultrasimple atom-efficient electrophilic amination reagents for phenols and indoles under metal-free conditions.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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An environment-friendly 2 – cyano phenothiazine industrial preparation method (by machine translation)

This invention provides an environment-friendly 2 – cyano phenothiazine industrial preparation method, the method uses 2 – chloro phenothiazine and cuprous cyanide as raw materials, to high boiling organic solvent as the solvent, alkali metal halide as a catalyst to the high temperature should, in the refluxing reaction before, under the protection of inert gas, including the raw materials, solvent and catalyst reaction system by azeotropic water, azeotropic water after refluxing reaction, the temperature of the reflux after the completion of the reaction, the reaction product after processing and extraction, to obtain crude, obtained after purification of the 2 – cyano phenothiazine. In order to control the amide impurity, the azeotropic water, avoids the use of phosphorus oxychloride treatment complicated process, while avoiding the use of acyl chloride or concentrated sulfuric acid dehydration to generate highly toxic gas hydrocyanic acid, is conducive to large scale industrial production. Recovery of the 1st organic solvent, can be repeated application, the production cost is reduced. (by machine translation)

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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A NOVEL SYNTHETIC ROUTE TO CYANOPHENOTHIAZINES. FIRST EXAMPLE OF SMILES REARRANGEMENT FROM HALOGENOBENZONITRILES

The reaction of halogenobenzonitriles with 2-aminobenzenethiol gave, by a Smiles rearrangement 2-mercaptocyanodiphenylamines which are cyclised to cyanophenothiazines via a disulfide intermediate.A mechanism is proposed.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Method for synthesizing N – aryl phenothiazine compounds (by machine translation)

The invention discloses a method for synthesizing N – aryl phenothiazine compounds, which belongs to the technical field of organic chemistry. In order to indole compounds 1 and phenothiazine 2 as reaction raw material, cuprous bromide as a catalyst, in a polar aprotic solvent, under the air atmosphere of the reaction, the obtained N – aryl substituted phenothiazine compounds 3. The invention using air as the oxidizing agent, with green, economic, and environmental protection, the use of the indole and phenothiazine between dehydrogenation C (sp2 ) – H/N – H cross-coupling, constructing the model C – N key, widens the N – aryl phenothiazine compound synthesis method. (by machine translation)

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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An Inhibitor of the Interaction of Survivin with Smac in Mitochondria Promotes Apoptosis

Herein we report the first small molecule that disrupts the survivin-Smac interaction taking place in mitochondria. The inhibitor, PZ-6-QN, was identified by initially screening a phenothiazine library using a fluorescence anisotropy assay and then conducting a structure?activity relationship study. Mutagenesis and molecular docking studies suggest that PZ-6-QN binds to survivin similarly to the known Smac peptide, AVPI. The results of the effort also show that PZ-6-QN exhibits good anticancer activity against various cancer cells. Moreover, cell-based mechanistic studies provide evidence for the proposal that PZ-6-QN enters mitochondria to inhibit the survivin-Smac interaction and promotes release of Smac and cytochrome c from mitochondria into the cytosol, a process that induces apoptosis in cancer cells. Overall, the present study suggests that PZ-6-QN can serve as a novel chemical probe for study of processes associated with the mitochondrial survivin-Smac interaction and it will aid the discovery of novel anticancer agents.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Efficient and regioselective synthesis of phenothiazine via ferric citrate catalyzed C-S/C-N cross-coupling

Efficient C-S and C-N cross-coupling reactions have been developed for regioselective, scalable and environmentally benign synthesis of substituted phenothiazine derivatives. Cross-coupling reactions were demonstrated on various challenging substrates using non-toxic, highly economical, readily available ferric citrate as a catalyst to get desired product with high regioselectivity. Atom economy is the added advantage of this protocol since additional N-protection step before coupling and eventual deprotection of the same to obtain the desired product arenot required. To the best of our knowledge, this is the first report on the use of inexpensive ferric citrate as a catalyst without involving any ligand for the synthesis of regioselectively substituted phenothiazine.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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A Facile Synthesis of Cyanophenothiazines

A one-pot synthesis of 1, 3 and 4-cyanophenothiazines and a two-step approach to 2-cyanoisomer have been developed. The condensation of 2-aminobenzenethiol and 2,3 or 3,4-dihalogenobenzonitriles followed by Smiles rearrangement or by intramolecular aromatic substitution gave the desired ring systmes.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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A metal- and oxidizing-reagent-free anodic para-selective amination of anilines with phenothiazines

A highly para-selective amination of anilines with phenothiazines for producing various functionalized 10-aryl-10H-phenothiazines is reported. The oxidative amination reaction proceeds electrochemically at room temperature, thereby avoiding the use of metals and oxidizing reagents with excellent functional group tolerance and broad substrate scope.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Electrochemical oxidation induced selective tyrosine bioconjugation for the modification of biomolecules

Directly introducing a beneficial functional group into biomolecules under mild, clean and easy-to-handle conditions is of great importance in the field of chemical biology and pharmacology. Herein, we described an electrochemical strategy to perform the bioconjugation of tyrosine residues with phenothiazine derivatives in a rapid and simple manner. In this electrochemical system, various polypeptides and proteins were successfully labelled with excellent site-and chemo-selectivity, and metals, oxidants or additives were also avoided.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Electrochemical Oxidative C?H Amination of Phenols: Access to Triarylamine Derivatives

Dehydrogenative C?H/N?H cross-coupling serves as one of the most straightforward and atom-economical approaches for C?N bond formation. In this work, an electrochemical reaction protocol has been developed for the oxidative C?H amination of unprotected phenols under undivided electrolytic conditions. Neither metal catalysts nor chemical oxidants are needed to facilitate the dehydrogenation process. A series of triarylamine derivatives could be obtained with good functional-group tolerance. The electrolysis is scalable and can be performed at ambient conditions.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem