Archives for Chemistry Experiments of 2-Cyano-phenothiazine

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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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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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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

 

Archives for Chemistry Experiments of 2-Cyano-phenothiazine

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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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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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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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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

 

Extended knowledge of 2-Cyano-phenothiazine

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PHENOTHIAZINE ANALOGUES AS MITOCHONDRIAL THERAPEUTIC AGENTS

The present disclosure provides phenothiazine derivative compounds and salts thereof, compositions comprising these compounds, and methods of using these compounds in a variety of applications, such as treatment or suppression of diseases associated with decreased mitochondrial function resulting in diminished ATP production and/or oxidative stress and/or lipid peroxidation.

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

 

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Synthesis of deuterium-labeled cyamemazine and monodesmethyl cyamemazine

A novel approach is presented for the synthesis of cyamemazine maleate and N-desmethyl cyamemazine maleate using a 10-(amino-2-methylpropyl)phenothiazine derivative. This method was successfully applied to the synthesis of [ 2H6]cyamemazine maleate and N-desmethyl-[ 2H3]cyamemazine maleate.

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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