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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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Why Have Clinical Trials of Antioxidants to Prevent Neurodegeneration Failed? – A Cellular Investigation of Novel Phenothiazine-Type Antioxidants Reveals Competing Objectives for Pharmaceutical Neuroprotection

Purpose: Only a fraction of the currently established low-molecular weight antioxidants exhibit cytoprotective activity in living cells, which is considered a prerequisite for their potential clinical usefulness in Parkinson?s disease or stroke. Post hoc structure-activity relationship analyses have predicted that increased lipophilicity and enhanced radical stabilization could contribute to such cytoprotective activity. Methods: We have synthesized a series of novel phenothiazine-type antioxidants exhibiting systematic variation in their lipophilicity and radical stabilization. Phenothiazine was chosen as lead structure for its superior activity at baseline. The novel compounds were evaluated for their neuroprotective potency in cell culture, and for their primary molecular targets. Results: Lipophilicity was associated with enhanced cytoprotective activity, but only to a certain threshold (logP ? 7). Benzannulation likewise produced improved cytoprotectants that exhibited very low EC50 values of ~8?nM in cultivated neuronal cells. Inhibition of global protein oxidation was the best molecular predictor of cytoprotective activity, followed by the inhibition of membrane protein autolysis. In contrast, the inhibition of lipid peroxidation in isolated brain lipids and the suppression of intracellular oxidant accumulation were poor predictors of cytoprotective activity, primarily as they misjudged the cellular advantage of high lipophilicity. Conclusions: Lipophilicity, radical stabilization and molecular weight appear to form an uneasy triangle, in which a slightly faulty selection may readily abolish neuroprotective activity.

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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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Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. I hope my blog about is helpful to your research. Safety of 2-Cyano-phenothiazine

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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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Identification of a non peptidic RANTES antagonist

A series of phenothiazines demonstrating inhibition of RANTES binding to THP-1 cell membranes has been identified. The lead compound RP23618 (IC50 = 3 muM) was found to inhibit specific binding of 125I-RANTES, but not 125I-MCP-1 to THP-1 cell membranes and furthermore to antagonise RANTES, but not MCP-1-induced chemotaxis of THP-1 cells.

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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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2-Azaadamantane N-oxyl (AZADO)/Cu Catalysis Enables Chemoselective Aerobic Oxidation of Alcohols Containing Electron-Rich Divalent Sulfur Functionalities

The chemoselective oxidation of alcohols containing electron-rich sulfur functionalities (e.g., 1,3-dithianes and sulfides) into their corresponding carbonyl compounds with the sulfur groups can sometimes be a demanding task in modern organic chemistry. A reliable method for this transformation, which features azaadamantane-type nitroxyl radical/copper catalysis using ambient air as the terminal oxidant is reported. The superiority of the developed method was demonstrated by comparing it with various conventional alcohol oxidation methods.

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

 

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Mild, Periodate-Mediated, Dehydrogenative C-N Bond Formation with Phenothiazines and Phenols

The dehydrogenative amination of phenols with phenothiazines was achieved in transition-metal-free conditions, utilizing cheap sodium periodate as oxidant, at low temperature. A significantly larger scope of phenol substrates was tolerated compared to previous methods.

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

 

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Electrooxidative para-selective C?H/N?H cross-coupling with hydrogen evolution to synthesize triarylamine derivatives

Oxidative C?H/N?H cross-coupling is one of the most atom-economical methods for the construction of C?N bonds. However, traditional oxidative C?H/N?H cross-coupling either required the use of strong oxidants or high reaction temperature, which makes it difficult to tolerate redox active functional groups. Herein we describe an external chemical oxidant-free electrooxidative C?H/N?H cross-coupling between electron-rich arenes and diarylamine derivatives. Under undivided electrolytic conditions, a series of triarylamine derivatives are produced from electron-rich arenes and diarylamine derivatives with high functional group tolerance. Both of the coupling partners are redox active in oxidative C?H/N?H cross-coupling, which enables high regioselectivity in C?N bond formation. Exclusive para-selectivity is observed for the coupling with anilines.

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

 

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Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. I hope my blog about is helpful to your research. Computed Properties of C13H8N2S

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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.

Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. I hope my blog about is helpful to your research. Computed Properties of C13H8N2S

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