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3,6-Diazaphenothiazines as potential lead molecules – synthesis, characterization and anticancer activity

3,6-Diazaphenothiazines were obtained in cyclization of 3-amino-3′-nitro-2,4′-dipyridinyl sulfide and the reaction of sodium 3-amino-2-pyridinethiolate with 4-chloro-3-nitropyridine followed by alkylation and heteroarylation. The thiazine ring formation ran via the Smiles rearrangement. The structure elucidation was based on 2D NMR and X-ray analysis of N-methylated product. 3,6-Diazaphenothiazines were investigated for antitumor activity using glioblastoma SNB-19, melanoma C-32 and breast cancer MCF-7 cells. 10H-3,6-diazaphenothiazine was 10 times more active (IC50 < 0.72 mu g/mL) than cisplatin. Two diazaphenothiazines with the 2-pyrimidinyl and dimethylaminopropyl substituents were selectively active against MCF-7 and C-32 cells. The expressions of H3 (proliferation marker), TP53, CDKN1A (cell cycle regulators), BAX and BCL-2 (proapoptopic and antiapoptopic genes) were detected by RT-QPCR method. The expression analysis suggests the cell cycle arrest and the mitochondrial apoptosis pathway activation in MCF-7 and SNB-19 cells. Do you like my blog? If you like, you can also browse other articles about this kind. Thanks for taking the time to read the blog about 7689-03-4, Category: thiazines.

Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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Structural Modifications of Surfactant-Assisted Alumina and Their Effectiveness for the Removal of Dyes

The current study focuses on the development of the modified surface of the alumina by anionic surfactant sodium dodecyl sulfate. The synthesized Surfactant Modified Alumina (SMA) effectively associated with dye molecules and amended their properties. The triphenylmethane (CBB) and thiazine dyes (MB) were selected as a simulated dye wastewater system. The removal was carried out by adsorption method under the optimized amount of adsorbent dosage, the concentration of adsorbate, contact time and temperature. The adsorption isotherm models like Langmuir, Freundlich and Dubinin Radushkevish were employed. The mechanism of the interaction represents the decolorized leuco dye molecules were formed after adsorption. Moreover, the thermodynamic parameters like (Delta S degrees), (Delta H degrees) and (Delta G degrees) were calculated represents the endothermic and spontaneous nature of the adsorption process. The pH at the point of zero charges (pHPZC) was determined. The photocatalytic degradation of respective dye systems was also observed. The surface morphology of (SMA) was determined by FT-IR and SEM techniques. Whereas the pseudo second order kinetics model was followed in the present system. The Pearson correlation Coefficient was conjointly applied. The removal efficiency was ascertained to be 99.50% for CBB(R-250) and 95.70% for (MB).

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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Ultrasound-assisted synthesis of highly functionalized benzo[1,3]thiazine via Cu-catalyzed intramolecular C-H activation reaction from isocyanides, aniline-benzoyl(acetyl) isothiocyanate adduct

A facile sonochemical route for the synthesis of benzo[1,3]thiazine derivatives via a one pot, multicomponent, intramolecular C-H activation reaction from isocyanides, aniline and benzoyl (acetyl) isothiocyanate adduct catalyzed by copper (I) iodide in acetone at 30 degrees C have been reported. The advantages of the described method include using simple and readily available starting materials and performing under mild copper-catalytic reaction conditions and also obtaining pure product with high yield without applying column chromatography. Furthermore, using the sonochemical methodology as an efficient method led to reduce the reaction times.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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The Reaction of 1-Phenylpyrazolidine-3,5-dione with Active Nitriles Using Phase Transfer Catalysis Conditions Technique

Heterocyclization reaction of 1-phenylpyrazolidine-3,5-dione with some active nitriles and acrylonitriles is described. These cyclization reactions afforded novel heterocyclic derivatives such as pyrano[2,3-c]pyrazoles, pyrazolyl-thiazole, pyrazolyl-1,3-thiazines, and pyrazolyl-1,3-oxathiino[6,5-c]pyrazoles. Heating 1-phenylpyrazolidine-3,5-dione alone under phase transfer catalysis conditions afforded the tricyclic dipyrazolofurandione. The structure of the new products has been characterized by IR, NMR, mass spectra, and their elemental analyses.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 3-{(2Z)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl}propanenitrile

The title compound, C18H12Cl2N2OS, consists of a dihydrobenzothiazine unit linked by a -CH group to a 2,4-dichlorophenyl substituent, and to a propanenitrile unit is folded along the S center dot center dot center dot N axis and adopts a flattened-boat conformation. The propanenitrile moiety is nearly perpendicular to the mean plane of the dihydrobenzothiazine unit. In the crystal, C-H-Bnz center dot center dot center dot N-Prpnit and C-H-Prpnit center dot center dot center dot O-Thz (Bnz = benzene, Prpnit = propanenitrile and Thz = thiazine) hydrogen bonds link the molecules into inversion dimers, enclosing R-2(2) (16) and R-2(2)(12) ring motifs, which are linked into stepped ribbons extending along [110]. The ribbons are linked in pairs by complementary C=O center dot center dot center dot Cl interactions. pi-pi contacts between the benzene and phenyl rings, [centroid-centroid distance = 3.974 (1) angstrom] may further stabilize the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H center dot center dot center dot H (23.4%), H center dot center dot center dot Cl/Cl center dot center dot center dot H (19.5%), H center dot center dot center dot C/C center dot center dot center dot H (13.5%), H center dot center dot center dot N/N center dot center dot center dot H (13.3%), C center dot center dot center dot C (10.4%) and H center dot center dot center dot O/O center dot center dot center dot H (5.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry calculations indicate that the two independent C-H-Bnz center dot center dot center dot N-Prpnit and CHPrpnit-O-Thz hydrogen bonds in the crystal impart about the same energy (ca 43 kJ mol(-1)). Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d, p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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Azafluorene Ornamented Thiazine Based Novel Fused Heterocyclic Organic Dyes for Competent Molecular Photovoltaics

Described herein is a series of azafluorene ornamented thiazine based novel fused heterocyclic organic dyes TBCPCA-1, TBCPCA-2, TBTCPCA-1 and TBTCPCA-2. Nanocrystalline titania based DSSC performance along with photophysical/electrochemical behaviors of the aforementioned dyes have been examined. Utilizing computational approach, distribution of electrons within the molecules has been explored. The devices possessing the novel fused dyes TBCPCA-1, TBCPCA-2, TBTCPCA-1 and TBTCPCA-2 as sensitizers exhibited overall power conversion efficiency range between 6.17 +/- 0.4 and 7.97 +/- 0.3%. The novel fused heterocyclic organic dyes featuring di-tert-butylazafluorene structural motif such as TBCPCA-1 and TBCPCA-2 exhibit higher power conversion efficiency than the ones carrying sterically congested tetra-tert-butyl-tri(azafluorene) scaffold viz., TBTCPCA-1 and TBTCPCA-2. Amongst the devices fabricated with the utilization of novel heterocyclic dyes as sensitizers, the device possessing the dye TBCPCA-2 as sensitizer displayed the highest power conversion efficiency of 7.97 +/- 0.3% along with a V-oc of 745 +/- 0.6 mV, a J(sc) of 16.92 +/- 0.3 mA.cm(-2) and a ff of 0.67 +/- 0.003. (C) 2017 Elsevier Ltd. All rights reserved.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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One-pot cis-selective route to sugar-fused thiazines via a masking-unmasking strategy in basic ionic liquid

A novel sequential Knoevenagel condensation, thia-Michael, and amino/mercaptoacetylative ring transformation reaction cascade for cis-selective synthesis of sugar-fused 1,3-thiazine is reported. The expeditious one-pot multicomponent annulation was performed using masked amino acid viz. 2-phenyl-1,3-oxazol-5-one or masked mercaptoacid viz. 2-methyl-2-phenyl-1,3-oxathiolan-5-one, D-xylose/D-glucose, and N-aryldithiocarbamic acid in ionic liquid [bmim] OH. The acetophenone obtained as a by-product and [bmim] OH itself could be easily recycled for further use without loss of efficiency. The envisaged method is operationally simple, high yielding, and excellent diastereoselective in favor of the cis-isomer of fused thiazines.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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One-pot cis-selective route to sugar-fused thiazines via a masking-unmasking strategy in basic ionic liquid

A novel sequential Knoevenagel condensation, thia-Michael, and amino/mercaptoacetylative ring transformation reaction cascade for cis-selective synthesis of sugar-fused 1,3-thiazine is reported. The expeditious one-pot multicomponent annulation was performed using masked amino acid viz. 2-phenyl-1,3-oxazol-5-one or masked mercaptoacid viz. 2-methyl-2-phenyl-1,3-oxathiolan-5-one, D-xylose/D-glucose, and N-aryldithiocarbamic acid in ionic liquid [bmim] OH. The acetophenone obtained as a by-product and [bmim] OH itself could be easily recycled for further use without loss of efficiency. The envisaged method is operationally simple, high yielding, and excellent diastereoselective in favor of the cis-isomer of fused thiazines.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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Uses of 1-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]-thiophen-2-yl)-3-dodecanoylthiourea as a Building Block in the Synthesis of Fused Pyrimidine and Thiazine Systems

The reaction of lauroyl isothiocyanate and 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile was used to synthesize the title compound 2. Compound 2 could serve as the main building block in the synthesis of many target heterocyclic systems. Various fused pyrimidines were synthesized in the reactions of compound 2 with sodium ethoxide, hydrazine hydrate, phenyl hydrazine, ethyl carbazate, thiourea, and/or 2-aminothiophenol. The structures of the synthesized compounds were confirmed by microanalytical and spectral data.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem

 

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Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photooxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates. (C) 2019 Elsevier Ltd. All rights reserved.

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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem