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1477-42-5, Name is 4-Methylbenzo[d]thiazol-2-amine, molecular formula is C8H8N2S, belongs to thiazole compound, is a common compound. In a patnet, once mentioned the new application about 1477-42-5, SDS of cas: 1477-42-5

3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK and F 96067). In the present study the further structure- activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK and F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

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Reference:
Thiazole | C3H9570NS – PubChem,
Thiazole | chemical compound | Britannica

A new application about 4-Methylbenzo[d]thiazol-2-amine

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Emodin is a cell arrest and apoptosis-inducing compound that is widely distributed in different plants (rhubarb, aloe), lichens and terrestrial fungi, and also isolated from marine-derived fungi and marine sponge-associated fungi. In this study, we designed and synthesized a novel series of emodin derivatives by binding emodin to an amino acid using linkers of varying lengths and composition, and evaluated their anti-proliferative activities using HepG2 cells (human hepatic carcinoma), MCF-7 cells (human breast cancer) and human normal liver L02 cells. Most of these derivatives showed moderate to potent anti-proliferative activities. Notably, compound 7a exhibited potent anti-proliferative activity against HepG2 cells with the half maximal inhibitory concentration (IC50) value of 4.95 muM, which was enhanced 8.8-fold compared to the parent compound emodin (IC50 = 43.87 muM), and it also exhibited better selective anti-proliferative activity and specificity than emodin. Moreover, further experiments demonstrated that compound 7a displayed a significant efficacy of inducing apoptosis through mitochondrial pathway via release of cytochrome c from mitochondria and subsequent activation of caspase-9 and caspase-3, inducing cell arrest at G0/G1 phase, as well as suppression of cell migration of tumor cells. The preliminary results suggested that compound 7a could be a promising lead compound for the discovery of novel anti-tumor drugs and has the potential for further investigations as an anti-cancer drug.

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Reference:
Thiazole | C3H9563NS – PubChem,
Thiazole | chemical compound | Britannica

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Rotacatenane is an interlocked compound composed of two mechanically interlocked macrocyclic components, i.e., a [2]catenane, and one axle component. In this paper we describe the selective synthesis of isomeric rotacatenanes. Two [2]rotaxanes with different phenanthroline moieties were synthesized by the oxidative coupling of an alkyne with a bulky blocking group, which proceeded in the cavity of the macrocyclic phenanthroline-Cu complex. The metal template method was used to install another cyclic component: the tetrahedral Cu(I) complex, which was composed of a [2]rotaxane and an acyclic phenanthroline derivative, was synthesized, and the cyclization of the phenanthroline derivative gave the rotacatenane. The sequential isomers of rotacatenanes were distinguished by 1H and 13C NMR spectroscopy.

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Reference:
Thiazole | C3H9558NS – PubChem,
Thiazole | chemical compound | Britannica

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Seven novel high refractive index (HRI) acrylic monomers, comprising the quinolinone structural motive, have been synthesized and characterized. Cross-linked homo- as well as copolymers were prepared by photochemical bulk polymerization. The homopolymers show refractive indices at 589 nm (n589) ranging from 1.60 up to 1.68, glass transition temperatures (Tg) from 52 to 76 C, and Abbe numbers (nuAbbe) of 19 to 25. Due to these parameters, the homopolymers are not suitable to be used directly for intraocular lens (IOL) manufacture, but the quinolinone monomers may be used as high refractive index components in copolymers. Potential mixtures were calculated theoretically and one example, a copolymer with PEA and PEGPEA, was prepared and characterized. The experimentally found values were Tg = 24 C, n589 = 1.593, and nuAbbe = 28.3. Interestingly, the quinolinone compound which does not have any spacer between the polymerizable group and the high refractive index group appears to be the most useful one. The lightfastness of the new material fulfills the demands for IOLs. Quinolinone derivatives are promising new comonomers for high refractive index copolymers.

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Reference:
Thiazole | C3H9557NS – PubChem,
Thiazole | chemical compound | Britannica

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Capture-Tag-Release: A Strategy for Small Molecule Labeling of Native Enzymes

A strategy for labeling native enzymes in a manner that preserves their activity is reported: capture?tag?release (CTR). Key to this approach is the small molecule CTR probe that contains an enzyme inhibitor, benzophenone crosslinker, and aryl phosphine ester. After UV-derived capture of the enzyme, addition of an azide-containing tag triggers a Staudinger ligation that labels the enzyme. A further consequence of the Staudinger ligation is fragmentation of the CTR probe, thus releasing the inhibitor and restoring enzymatic activity. As a proof-of-principle, the CTR strategy was applied to the hydrolase beta-galactosidase. The enzyme was efficiently labeled with biotin, and the kinetic data for the biotinylated enzyme were comparable to those for unlabeled beta-galactosidase. The CTR probe exhibits excellent targeting specificity, as it selectively labeled beta-galactosidase in a complex protein mixture.

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Reference:
Thiazole | C3H9566NS – PubChem,
Thiazole | chemical compound | Britannica

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1477-42-5, 4-Methylbenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The reaction carried out with 4-chloro-4-fluorobutyrophenone 7 (0.5ml, 3.04mmol) with imidazole 28 (0.21g, 3.04mmol) and K2CO3 (1g, 7.23mmol) in DMSO at 140C till the completion of reaction (TLC). After the completion of reaction, the workup was done with ethylacetate and water and then the organic layer was separated, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The latter was purified by silica gel (60-120 mesh) column chromatography using ethylacetate: hexane (1:1) as eluent to give the title compound in 80% yield (0.51g), 1477-42-5

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Reference£º
Article; Singh, Kartikey; Sona, Chandan; Ojha, Vikash; Singh, Maninder; Mishra, Ankita; Kumar, Ajeet; Siddiqi, Mohammad Imran; Tripathi, Rama P.; Yadav, Prem N.; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 499 – 516;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

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1477-42-5, 4-Methylbenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Add commercially available 2-amino-4-methy-benzothiazole (10 g, 61 mmol) portionwise to a black solution of copper (II) bromide (16 g, 73 mmol) and TERT-BUTYL nitrite (11.9 mL, 99 mmol) in acetonitrile (220 mL) at room temperature under nitrogen over the course of five min and stir the mixture for 30 min. Dilute the mixture with 1 N HCL (500 mL) and extract with ethyl acetate (3 x 500 mL). Wash the combined organic extracts with 1 N HCL (250 mL), dry over MGS04 and remove the solvents under reduced pressure. Purify the residue by filtration through a plug of silica gel, eluting with ethyl acetate (500 mL), and remove the solvents under reduced pressure to afford 2-bromo-4-methylbenzothiazole (Step 1) as a black solid (12.68 g, 91%): 1H NMR (CDCL3) 6 2.70 (s, 1H), 7.20 (m, 2H), 7.60 (d, 1H) ; APCI mass spectrum M/Z 228 [C8H6NSBR + H] +., 1477-42-5

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Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/63155; (2004); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1477-42-5,4-Methylbenzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 18: 4-METHYL-2-HYDRAZINOBENZOTHIAZOLE To a suspension of 4-methyl-2-aminobenzothiazole (5.0 g., 0.03 mole) in 20 ml. of ethylene glycol was added 5.4 g. of 85% hydrazine hydrate (0.09 mole) and 2.75 g. (0.046 mole) acetic acid. The mixture was heated to 126C. under N2 atmosphere for 3 hours. On cooling and dilution with about 1/2 volume of water the product crystallized.

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Reference£º
Patent; Eli Lilly and Company; US3937714; (1976); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1477-42-5,4-Methylbenzo[d]thiazol-2-amine,as a common compound, the synthetic route is as follows.,1477-42-5

Step 1: 4-methyl-3H-benzothiazol-2-one 5.00 g (30.5 mmol) 2-amino-4-methylbenzothiazole in 15.0 mL formic acid, 6.10 mL glacial acetic acid and 112 mL conc. hydrochloric acid were cooled to -5 C. with stirring and slowly combined with a solution of 2.10 g (30.5 mmol) sodium nitrite in 5.0 mL water. The reaction mixture was stirred for 20 min at this temperature, then heated to RT and then refluxed overnight. The cooled mixture was then mixed with water and extracted several times with EtOAc. The combined organic phases were washed with saturated sodium chloride solution, dried on sodium sulphate, filtered and the filtrate was evaporated down. Yield: 3.70 g (74% of theoretical) ESI-MS: m/z=164 (M-H)-

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Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/59954; (2011); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

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1477-42-5, 4-Methylbenzo[d]thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 4-methyl-2-aminobenzothiazole (164 mg, 1.0 mmol) in dichloromethane (20 mL) was added 1-Ethyl-3-(3-Dimethylaminopropyl)carbodiimide (EDC) (191 mg, 1.0 mmol) and 1-hydroxy-1,2,3-benzotriazole (HOBt) (13.5 mg, 0.1 mmol). Then added 2-{2-methoxy-5-[(E)-3-oxo-3-(3,4,5-trimethoxy phenyl)-1-propenyl]phenoxy}acetic acid (2) (402 mg, 0.1 mmol) and the reaction mixture was stirred at a temperature of 25 C. for 24 h and the reaction was monitored by TLC. Then to this water is added and extracted with dichloromethane. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate and hexane as solvent system to obtain the pure product (9k) (440 mg, 80% yield) 1H NMR (CDCl3): delta 10.71 (br s, 1H), 7.76 (d, 1H, J=15.4 Hz), 7.65-7.70 (m, 1H), 7.32-7.43 (m, 4H), 7.28 (s, 2H), 7.22-7.26 (m, 1H), 7.02 (d, 1H, J=8.4 Hz), 4.86 (s, 2H), 4.09 (s, 3H), 3.96 (s, 6H), 3.94 (s, 3H), 2.67 (s, 3H); ESIMS: 549 (M+1)+.

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Reference£º
Patent; Ahmed, Kamal; Reddy, Adla Malla; Paidakula, Suresh; Rao, Neigapula Sankara; Shetti, Rajesh V. C. R. N. C.; US2013/317231; (2013); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica