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Regioselective Synthesis of Functionalized 1,3-Thiazine-4-ones via Multicomponent Click Reaction Approach

Herein, we disclose a synthetic strategy for the preparation of functionalized thiazinones under exceptionally ambient condition via domino multicomponent click reaction. The protocol utilizes readily available starting materials: phenylisothiocyanates, hydrazine monohydrate and diethyl but-2-ynedioate or dimethyl but-2-ynedioate. The reaction condition merely requires mixing of substrates at room temperature without using any catalyst and/or solvent.

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

 

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Quinoline-Based Polyazaheterocycles by a Hydrogen Peroxide-Mediated Isocyanide Insertion

An efficient and green protocol for the synthesis of quinoline-based polyazaheterocycles with 2-(2-mercaptoquinolin-3-yl)-2,3-dihydroquinazolin-4(1H)-ones and aliphatic and aromatic isocyanides using hydrogen peroxide is described.

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

 

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Synthesis of Novel Heterocyclic Compounds Incorporate 4,5,6,7-Tetrahydrobenzo[b]thiophene Together with Their Cytotoxic Evaluations

The 2-amino-3-cyano-4,5,6,7-tetrahydrobenzolbithiophene was the key starting compound used to synthesize new thiazole, pyrimidine, pyran, pyridine and thiazine derivatives. The cytotoxicity of the synthesized compounds was studied towards the three cancer cell lines namely MCF-7 (breast adenocarcinorna), NCI-H460 (non-small cell lung cancer) and SF-268 (central nervous system (CNS) cancer) in addition to the normal cell line (WI-38) using doxorubicin as the reference drug. The study showed that compounds 5, 9a, 15b, 17c, 18 and 21b were the most potent compounds.

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

 

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An operational study comparing microscopes and staining variations for tuberculosis LED FM

SETTING: Tuberculosis control projects, Damien Foundation Bangladesh. OBJECTIVES: To compare transmitted fluorescence (Olympus CX21 (TM)/FRAEN FluoLED (TM)) with epi-fluorescence (Zeiss Primostar iLED (TM)) light-emitting diode microscopes (LED-FM) and various auramine staining and destaining/counterstaining techniques for the detection of acid-fast bacilli. DESIGN: Multicentre blinded reading of routine smears on both types of microscopes using different staining techniques in multiple phases. LED-FM rechecking of discordant series with and without restaining to calculate operating characteristics. RESULTS: Among 64 874 smears, both instruments detected 9.6% positives. Compared to the standard technique, the stronger auramine-O formulation did not perform better. Thiazine red counterstaining tended to yield more false-positive as well as false-negative errors. Combined destaining/counterstaining (sensitivity 93%, positive predictive value [PPV] 98%) proved significantly less effective. Both destaining with 1% hydrochloric acid (HCl) and 10% alcohol and the standard 0.5% HCl and 70-95% alcohol were equally accurate (sensitivity 95-96%, PPV 99%). The sturdiness of the microscopes in field conditions was sub-optimal: only 5/16 instruments did not break down. CONCLUSIONS: Both microscopes performed equally well. The standard staining technique is as good as the more complicated and expensive variations. A destaining solution containing only 10% alcohol works perfectly well. The inferior quality of LED-FM microscope components is an obstacle to FM expansion.

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

 

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Crystal structure of (E)-2-benzylidene-4-[(3-phenyl-4,5-dihydroisoxazol-5-yl)-methyl]-2H-benzo[b][1,4] thiazin-3(4H)-one

In the title compound, C25H20N2O2S, the dihydroisoxazole ring exhibits an envelope conformation with the methine atom being the flap, while the 1,4-thiazine ring displays a screw-boat conformation. The six-membered ring fused to the 1,4-thiazine ring makes dihedral angles of 63.04 (2) and 54.7 (2)degrees with the mean planes through the five-membered heterocycle and the attached phenyl ring, respectively. The phenyl group connected to the 1,4-thiazine ring is disordered over two sites [major component = 0.57 (2)]. The most prominent interactions in the crystal structure are C-H center dot center dot center dot O hydrogen bonds that link molecules, forming inversion dimers, and C-H center dot center dot center dot N hydrogen bonds that link the dimers into columns parallel to the b axis.

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

 

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A facile access and evaluation of some novel thiazole and 1,3,4-thiadiazole derivatives incorporating thiazole moiety as potent anticancer agents

Background: Many heterocyclic compounds containing thiazole or 1,3,4-thiadiazole ring in their skeletons have been reported to possess various pharmacological activities especially anticancer activities. Results: 4-Methyl-2-phenylthiazole-5-carbohydrazide (2) was used as a synthon to prepare 2-(4-methyl-2-phenylthiazole-5-carbonyl)-N-phenylhydrazinecarbothioamide (3) and 2-(2-(4-methyl-2-phenylthiazole-5-carbonyl) hydrazono)-N’-phenylpropane hydrazonoyl chlorides 5a-c. In addition, thioamide 3 was used as starting material for preparation of a new series of thiadiazole derivatives via its reaction with hydrazonoyl chlorides 5a-c in dioxane using triethylamines as catalyst. In addition, a series of thiazole derivatives was synthesized by reaction of thioamide 3 with a number of a-halo compounds, namely, 3-chloropentane-2,4-dione (8) or 2-chloro-3-oxo-N-phenyl butanamide (10) phenacyl bromide 12 ethyl chloroacetate (14) in EtOH in the presence of triethylamine. The structures assigned for all the new products were elucidated based on both elemental analyses and spectral data and the mechanisms of their formation was also discussed. Moreover, the new products was evaluated in vitro by MTT assays for their anticancer activity against cell lines of Hepatocellular carcinoma cell line (HepG-2). The best result observed for compounds 7b (IC50 = 1.61 +/- 1.92 (mu g/mL)) and 11 (IC50 = 1.98 +/- 1.22 (mu g/mL)). The structure-activity relationships have been suggested based on their anticancer results. Conclusions: A novel series of new pharmacophores containing thiazole moiety have been synthesized using a facile and convenient methods and evaluated as potent anticancer agents.

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

 

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Synthesis and In Vitro Anticancer Evaluation of Symmetrically Bridged 1,3-thiazine Derivatives

A series of bis-1,3-thiazine derivatives 3a-o were synthesized from the condensation reactions of symmetric dialdehydes 1a-c possessing aliphatic ether spacer units with 3-substituted-amino-2-cyano-3-mercaptoacrylamides 2a-e. The chemical structures of the products were fully characterized by using different spectroscopic techniques, such as H-1 NMR, C-13 NMR, IR, electron impact mass spectrometry, and elemental analysis. Compounds 3a, 3f, and 3k underwent ring opening followed by recyclization and alkylation in basic medium to afford bis-pyrimidinones 4a-c and 5a-c. The anticancer potential of the new bis-1,3-thiazines was assessed in vitro against six different human cell lines, including lung A549, colon HCT116, breast MCF-7, prostate PC3, liver HepG2, and normal melanocyte HFB4. The results revealed a potent activity of compounds 3e and 3k against breast and liver cancer cell lines in comparison with the reference drug doxorubicin with no noticeable toxicity on normal cells.

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

 

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New Advances in Chemical Research, May 2021. We’ll be discussing some of the latest developments in chemical about CAS: 20277-69-4, Name is Sodium methanesulfinate, belongs to thiazines compound, is a common compound. In a pantent, author is El Malah, Tamer, once mentioned the new application about 20277-69-4, Quality Control of Sodium methanesulfinate.

Synthesis and In Vitro Anticancer Evaluation of Symmetrically Bridged 1,3-thiazine Derivatives

A series of bis-1,3-thiazine derivatives 3a-o were synthesized from the condensation reactions of symmetric dialdehydes 1a-c possessing aliphatic ether spacer units with 3-substituted-amino-2-cyano-3-mercaptoacrylamides 2a-e. The chemical structures of the products were fully characterized by using different spectroscopic techniques, such as H-1 NMR, C-13 NMR, IR, electron impact mass spectrometry, and elemental analysis. Compounds 3a, 3f, and 3k underwent ring opening followed by recyclization and alkylation in basic medium to afford bis-pyrimidinones 4a-c and 5a-c. The anticancer potential of the new bis-1,3-thiazines was assessed in vitro against six different human cell lines, including lung A549, colon HCT116, breast MCF-7, prostate PC3, liver HepG2, and normal melanocyte HFB4. The results revealed a potent activity of compounds 3e and 3k against breast and liver cancer cell lines in comparison with the reference drug doxorubicin with no noticeable toxicity on normal cells.

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

 

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Synthesis and L-type calcium channel blocking activity of new chiral oxadiazolothiazinones

Oxadiazolo[3,4-c][1,4]thiazin-3-ones are cardiovascular agents that block L-type calcium channels. Previous data of cardiac and vasorelaxant activity on guinea-pig for several derivatives indicated the two positions ortho to the thiazine’s sulphur as crucial for modulating the activity; but these positions are likely susceptible to metabolic biotransformations, as indicated by in silico predictions. We designed new derivatives, and obtained three negative inotropic agents with EC50 in the low nanomolar range, more potent than all the precursors published so far. In particular, benzocondensation at the thiazine ring led to 3a (EC50 = 0.013 mu M) and 3b (EC50 = 0.006 mu M). Besides negative inotropy, we also observed relaxant activity on nonvascular muscle in the micromolar range. We resolved the new derivatives by chiral chromatography, and determined their absolute configuration by comparing experimental and calculated chiroptical properties (VCD, ECD and ORD): they hold the same absolute configuration-optical rotation relationship, (S)-(+)I(R)-(-). Both cardiac and nonvascular activity are majorly or mostly retained in the R-form for all the compounds, but for the nonvascular activity we observed a strong stereoselectivity for 3a, with the R-form in the nanomolar range (IC50 = 0.020 mu M) and 259-fold more potent than the S-one. (C) 2015 Elsevier Masson SAS. All rights reserved.

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

 

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Organic-inorganic hybrid layer-by-layer electrostatic self-assembled film of cationic dye Methylene Blue and a clay mineral: Spectroscopic and Atomic Force microscopic investigations

The metachromic cationic dye Methylene Blue (MB) belongs to the thiazine class of organic dye. This dye cation can interact electrostatically with inorganic clay mineral Montmorillonite (MMT) to form organic inorganic hybrid layer-by-layer (LbL) self-assembled film onto a poly(allylamine hydrochloride) coated quartz substrate. The degree of dye aggregations in LbL films was found to depend on concentrations of both MMT clay and MB in LbL self-assembled films as evidenced by UV vis absorption spectroscopic technique. The adsorption of dye molecules to the LbL films was found to a two-step exponential process: first step was very fast and the later process had a much delay period. Also the assembling behavior and organizations of MB molecules in the host clay matrix in LbL films significantly depend on pH of dye solution from which LbL film was fabricated. For MMT/MB mixed solution the pi-pi transition of absorption bands of MB shifted to lower wavelength due to the formation of large number of H-aggregates in their mixed aqueous solution. Fourier Transform infrared (in ATR mode) spectroscopic method was employed to explore the electrostatic interaction between clay MMT and MB in LbL films. Atomic Force microscopic image of hybrid LbL films revealed the surface morphology and roughness profile of the organic-inorganic hybrid molecular assemblies onto the solid substrate. (C) 2017 Elsevier B.V. All rights reserved.

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