More research is needed about 2-Cyano-phenothiazine

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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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Lipophilic methylene blue analogues enhance mitochondrial function and increase frataxin levels in a cellular model of Friedreich’s ataxia

Friedreich’s ataxia (FRDA) is an autosomal recessive neurodegenerative disorder resulting from reduced expression of the protein frataxin (FXN). Although its function is not fully understood, frataxin appears to help assemble iron sulfur clusters; these are critical for the function of many proteins, including those needed for mitochondrial energy production. Finding ways to increase FXN levels has been a major therapeutic strategy for this disease. Previously, we described a novel series of methylene violet analogues and their structural optimization as potential therapeutic agents for neurodegenerative and mitochondrial disorders. Presently, a series of methylene blue analogues has been synthesized and characterized for their in vitro biochemical and biological properties in cultured Friedreich’s ataxia lymphocytes. Favorable methylene blue analogues were shown to increase frataxin levels and mitochondrial biogenesis, and to improve aconitase activity. The analogues were found to be good ROS scavengers, and able to protect cultured FRDA lymphocytes from oxidative stress resulting from inhibition of complex I and from glutathione depletion. The analogues also preserved mitochondrial membrane potential and augmented ATP production. Our results suggest that analogue 5, emerging from the initial structure of the parent compound methylene blue (MB), represents a promising lead structure and lacks the cytotoxicity associated with the parent compound MB.

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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

 

Discovery of 2-Cyano-phenothiazine

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O2-mediated dehydrogenative amination of phenols

A method was developed for the direct dehydrogenative construction of C-N bonds between unprotected phenols and a series of cyclic anilines without resorting to any kind of metal activation of either substrate and without the use of halides. The resulting process relies on the exclusively organic activation of molecular oxygen and the subsequent oxidation of the aniline substrate. This allows the coupling of ubiquitous phenols, thus furnishing aminophenols through an atom-economical and most sustainable dehydrogenative amination method. This new reactivity, which relies on the intrinsic organic reactivity of cumene in what can be seen as a modified Hock activation process of oxygen, is expected to have a large impact on the formation of C-N bonds in organic synthesis.

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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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Visible-Light-Promoted Direct Amination of Phenols via Oxidative Cross-Dehydrogenative Coupling Reaction

A transition-metal-free approach was disclosed for intermolecular aryl C-N bonds formation between phenols and cyclic anilines via cross-dehydrogenative coupling (CDC) amination that was mediated by visible light, wherein K2S2O8 served as an external oxidant. The salient features of this protocol include circumventing the requirement for prefunctionalized starting materials and achieving single regioselectivity of amination adducts at room temperature.

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

 

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A 2 – cyano phenothiazine preparation method (by machine translation)

The invention relates to a preparation method of 2-cyanophenothiazine. Dehydration reaction is firstly performed, thereby avoiding the complex technical step of performing dehydration refinement after the 2-cyanophenothiazine crude product is generated, and effectively reducing the product decomposition; meanwhile, the 2-cyanophenothiazine generation reaction is performed after dehydration to obviously reduce the recrystallization frequency in the refinement process, so that the recrystallization is only needed once, thereby greatly reducing the loss of the materials and energy sources, lowering the preparation cost and enhancing the reaction yield; and thus, the yield of the preparation method can reach 90.3% or above. Besides, the purity of the product is very high and can reach 99.5% or above, and the content of the impurity amide is less than 0.1%. In addition, the catalyst used by the method can effectively accelerate the reaction, shorten the reaction time and lower the reaction temperature, thereby enhancing the energy utilization ratio and further lowering the cost of the whole preparation process.

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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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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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Synthesis and structure-activity relationships of phenothiazine carboxylic acids having pyrimidine-dione as novel histamine H1 antagonists

A series of phenothiazine carboxylic acid derivatives, having 6-amino-pyrimidine-2,4(1H,3H)-dione moiety via a appropriate linker, were synthesized and evaluated for their affinity toward human histamine H1 receptor and Caco-2 cell permeability. Selected compounds were further evaluated for their oral anti-histaminic activity in mice and bioavailability in rats. Finally, promising compounds were examined for their anti-inflammatory potential in mice OVA-induced biphasic cutaneous reaction model. Among the compounds tested, phenothiazineacetic acid compound 27 showed both histamine H1-receptor antagonistic activity and anti-inflammatory activity in vivo model.

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