Current achievements and perspectives in synthesis and applications of 3,7-disubstituted phenothiazines as Methylene Blue analogues

Padnya, Pavel L.; Khadieva, Alena I.; Stoikov, Ivan I.

doi:10.1016/j.dyepig.2022.110806

Cited by 15 publications

(12 citation statements)

References 155 publications

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“…The phenothiazines and the phenazines are exceptional and versatile classes of electron-rich nitrogen heterocycles with broad pharmaceutical profiles and rich materials sciences applications [ 1 , 2 , 3 ]. A seemingly small difference between these types of molecules, i.e., the presence of a six-membered ring with nitrogen and sulfur atoms for phenothiazines and two nitrogen atoms for phenazines, manifests itself profoundly through their physicochemical and structural properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

et al. 2022

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Two unique structures were isolated from the phosphorylation reaction of 10H-phenothiazine. The 5,5-dimethyl-2-(10H-phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide (2a) illustrates the product of N-phosphorylation of phenothiazine. Moreover, a potential product of 2a instability, a thiophosphoric acid 2b, was successfully isolated and structurally characterized. Molecule 2a, similarly to sulfoxide derivative 3, possesses interesting phosphorescence properties due to the presence of d-pπ bonds. The X-ray, NMR, and DFT computational studies indicate that compound 2a exhibits an anomeric effect. Additionally, the syntheses of selected symmetrical and unsymmetrical pyridine-embedded phenazines were elaborated. To compare the influence of phosphorus and sulfur atoms on the structural characteristics of 10H-phenothiazine derivatives, the high-quality crystals of (4a,12a-dihydro-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxalin-12-yl)(phenyl)methanone (1) and selected phenazines 5,12-diisopropyl-3,10-dimethyldipyrido[3,2-a:3′,2′-h]phenazine (5) and 5-isopropyl-N,N,3-trimethylpyrido[3,2-a]phenazin-10-amine (6a) were obtained. The structures of molecules 1, 2a, 2-mercapto-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (2b), 3,7-dinitro-10H-phenothiazine 5-oxide (3), 5 and 6a were determined by single-crystal X-ray diffraction measurements.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

et al. 2022

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“…In addition, it was suggested that due to the sedative and antiemetic properties, the phenothiazine compounds can have palliative outcome on chemotherapy side effects [ 23 ]. These data encouraged further research for the improvement of anticancer activity by structural modifications [ 24 ] with various heteroaromatic units [ 25 , 26 , 27 ], leading to promising results, with an in vivo tumor inhibition of approx. 70% being reported [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Antitumor Activity of PEGylated and TEGylated Phenothiazine Derivatives: Structure–Activity Relationship

Cibotaru¹,

Sandu²,

Nicolescu³

et al. 2023

IJMS

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The paper aims to investigate the antitumor activity of a series of phenothiazine derivatives in order to establish a structure–antitumor activity relationship. To this end, PEGylated and TEGylated phenothiazine have been functionalized with formyl units and further with sulfonamide units via dynamic imine bonds. Their antitumor activity was monitored in vitro against seven human tumors cell lines and a mouse one compared to a human normal cell line by MTS assay. In order to find the potential influence of different building blocks on antitumor activity, the antioxidant activity, the ability to inhibit farnesyltransferase and the capacity to bind amino acids relevant for tumor cell growth were investigated as well. It was established that different building blocks conferred different functionalities, inducing specific antitumor activity against the tumor cells.

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“…Their occurrence in several pharmaceutically active compounds such as promethazine, prochlorperazine, chlorpromazine, and many antipsychotic drugs is a testament to their growing importance in various fields of research (Figure ). − Synthetic methodologies for the construction and functionalization of phenothiazine are well explored in literature studies − and have helped promote the development of phenothiazine-based functional materials.…”

Section: Introductionmentioning

confidence: 99%

Phenothiazine-Based Cu(II)-Selective Fluorescent Sensor: GHK-Cu Sensing Applications

Sahu,

Yadav,

Gunturu

et al. 2023

J. Org. Chem.

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Sensing important metals in different environments is an important area and involves the development of a wide variety of metal-sensing materials. The employment of fluorescent sensors in metal sensing has been one of the most widely applied methodologies, and the identification of selective metal sensors is important. We herein report a phenothiazine-based Cu(II) fluorescent sensor that is highly selective to Cu(II) ions compared with other transition metal salts. The Lewis acidity of the Cu(II) salt certainly was found to be a factor for obtaining an enhanced sensing response in MeOH as the solvent, while a ratio of 1:1 was calculated to be the most optimum for getting the desired response.

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Current achievements and perspectives in synthesis and applications of 3,7-disubstituted phenothiazines as Methylene Blue analogues

Cited by 15 publications

References 155 publications

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

Antitumor Activity of PEGylated and TEGylated Phenothiazine Derivatives: Structure–Activity Relationship

Phenothiazine-Based Cu(II)-Selective Fluorescent Sensor: GHK-Cu Sensing Applications

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