55661-33-1归档 - Page 2 of 2 - Heterocyclic Building Blocks-Thiazole

Maryanoff, Bruce E. et al. published their research in ACS Medicinal Chemistry Letters in 2011 | CAS: 55661-33-1

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Category: thiazole

Inhibitors of Ketohexokinase: Discovery of Pyrimidinopyrimidines with Specific Substitution that Complements the ATP-Binding Site was written by Maryanoff, Bruce E.;O’Neill, John C.;McComsey, David F.;Yabut, Stephen C.;Luci, Diane K.;Jordan, Alfonzo D.;Masucci, John A.;Jones, William J.;Abad, Marta C.;Gibbs, Alan C.;Petrounia, Ioanna. And the article was included in ACS Medicinal Chemistry Letters in 2011.Category: thiazole This article mentions the following:

Attenuation of fructose metabolism by the inhibition of ketohexokinase (KHK; fructokinase) should reduce body weight, free fatty acids, and triglycerides, thereby offering a novel approach to treat diabetes and obesity in response to modern diets. We have identified potent, selective inhibitors of human hepatic KHK within a series of pyrimidinopyrimidines (1). For example, 8, 38, and 47 exhibited KHK IC₅₀ values of 12, 7, and 8 nM, resp., and also showed potent cellular KHK inhibition (IC₅₀ < 500 nM), which relates to their intrinsic potency vs KHK and their ability to penetrate cells. X-ray cocrystal structures of KHK complexes of 3, 8, and 47 revealed the important interactions within the enzyme’s ATP-binding pocket. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Category: thiazole).

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Aldrich, Leslie N. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2010 | CAS: 55661-33-1

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.HPLC of Formula: 55661-33-1

Total synthesis and biological evaluation of tambjamine K and a library of unnatural analogs was written by Aldrich, Leslie N.;Stoops, Sydney L.;Crews, Brenda C.;Marnett, Lawrence J.;Lindsley, Craig W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.HPLC of Formula: 55661-33-1 This article mentions the following:

The first total synthesis of tambjamine K (I) and a library of unnatural analogs was disclosed. Unnatural analogs were shown to be more potent in viability, proliferation, and invasion assays than the natural product in multiple cancer cell lines, with minimal to no cytotoxicity on non-transformed cell lines. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1HPLC of Formula: 55661-33-1).

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Aldrich, Leslie N. et al. published their research in Bioorganic & Medicinal Chemistry Letters in 2010 | CAS: 55661-33-1

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Downstream synthetic route of 55661-33-1

The synthetic route of 55661-33-1 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55661-33-1,Thiazol-2-ylmethanamine,as a common compound, the synthetic route is as follows.

Example 1286-Chloro-2-oxo-8-(2-oxo-2-((thiazol-2-ylmethyl)amino)ethyl)-1 ,2-dihydroquinoline- 3-carboxylic acid a) Methyl 6-chloro-2-methoxy-8-(2-oxo-2-(thiazol-2-ylmethylamino)ethyl)- quinoline-3-carboxylate[00366] Thiazol-2-yl-methylamine (104 muIota, 1 .10 mmol, 2.0 equiv.) is added to a suspension of (CO)sMoCINEt (220 mg, 0.55 mmol) in ethanol (5 mL). The resulting mixture is stirred under a nitrogen atmosphere for 2 h. Diglyme (5 mL) is added to the mixture and heated to 120 C with evaporation of ethanol. Tributylamine (144 muIota, 0.60 mmol, 1 .10 equiv.) and methyl 8-(bromomethyl)-6-chloro-2-methoxyquinoline-3- carboxylate (170 mg, 0.49 mmol, 0.9 equiv.) are added and the mixture is heated at 130 C for 2 h. The reaction mixture is filtered over kieselguhr and the filtrate is concentrated in vacuo. The residue is taken on hydromatrix and purified by flash column chromatography (silica, 1 -10% MeOH in DCM) to afford 89 mg (44%) of the title compound as a solid. 1H NMR (400 MHz, CDCI3), delta (ppm) 3.90 (s, 3H), 3.96 (s, 3H), 4.08 (s, 2H), 4.36 (d, 2H), 6.56 (br s, 1 H), 7.07-7.13 (m, 2H), 7.22-7.29 (m, 3H), 7.72 (s, 2H), 8.54 (s, 1 H). LC-MS: 399 [M+H] [35CI]., 55661-33-1

The synthetic route of 55661-33-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merz Pharma GmbH & Co. KGaA; ABEL, Ulrich; HANSEN, Angela; WOLTER, Falko Ernst; KRUEGER, Bjoern; KAUSS, Valerjans; ROZHKOVS, Jevgenijs; SEMENIHINA, Valentina; PISKUNOVA, Irena; PELSS, Juris; WO2012/164085; (2012); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Analyzing the synthesis route of 55661-33-1

55661-33-1 Thiazol-2-ylmethanamine 2756507, athiazole compound, is more and more widely used in various fields.

55661-33-1, Thiazol-2-ylmethanamine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

55661-33-1, To a round bottom flask with a magnetic stirrer bar 2-(aminomethyl)thiazole (0.46 g, 4 mmol) and 4-methoxybenzaldehyde (1 .22 g, 9 mmol) were added together with 10 ml methanol, NaCNBH3 (0.57 g, 9 mmol) and a few granules of 4A molecular sieve. The solution was stirred overnight at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC). After filtration the mixture was concentrated in vacuo and the resulting liquid was diluted with 50 ml dichloromethane and extracted with 3×50 ml 0.05 M HCI. The combined aqueous layer was made basic with NaOH until the pH was 10-1 1 and the solution was extracted with 2×150 ml dichloromethane. The organic layers were combined and dried over anhydrous MgS04, filtered and evaporated to give /V,/V-bis(4- methoxybenzyl)-1 -(thiazol-2-yl)methanamine as a dark brown oil. Yield: 1 g (70 %), ,1H NMR (300 MHz, CDCI3): delta 7.73 (1 H, d), 7.29 (5H, m), 6.9 (4H, m), 4.62 (2H, s), 4.13 (2H, s), 3.81 (8H, s),13C NMR (75 MHz, CDCI3): delta 172, 159.2, 158.9, 142.6, 133.4, 131 .8, 129.5, 128.7, 1 18.9, 1 14, 65, 55.4, 52.7, 50.1 .

55661-33-1 Thiazol-2-ylmethanamine 2756507, athiazole compound, is more and more widely used in various fields.

Reference£º
Patent; UNIVERSITETET I OSLO; TASKEN, Kjetil; LYGREN, Birgitte; ?STENSEN, Ellen; KLAVENESS, Jo; WO2013/171332; (2013); A2;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Simple exploration of 55661-33-1

As the paragraph descriping shows that 55661-33-1 is playing an increasingly important role.

Preparation of 3,5-di-tert-butyl-4-hydroxy-N-(1-(thiazol-2-ylmethylcarbamoyl)cyclopropyl)-benzamide; 1-(3,5-Di-tert-butyl-4-hydroxybenzamido)cyclopropanecarboxylic acid (100 mg, 0.3 mmol), thiazol-2-ylmethanamine (50 mg, 0.45 mmol), HATU (171 mg, 0.45 mmol) and DIPEA (0.15 mL, 0.9 mmol) were stirred in DCM at rt for 16 h. The organics were washed sequentially with saturated NaHCO3, 0.1 M HCl, dried (Na2SO4), concentrated in-vacuo and the residue purified by Biotage (5% MeOH/DCM) to give 3,5-di-tert-butyl-4-hydroxy-N-(1-(thiazol-2-ylmethylcarbamoyl)cyclopropyl)-benzamide (57 mg, 45.0%). MS: m/z=430.2 (calc’d for C23H31N3O3S 429.2).

As the paragraph descriping shows that 55661-33-1 is playing an increasingly important role.

Reference£º
Patent; Galemmo, JR., Robert; Holland, Richard; Hum, Gabriel; Pajouhesh, Hossein; Chahal, Navjot; Seid-Bagherzadeh, Mehran; Girard, Amy; US2009/270394; (2009); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Brief introduction of 55661-33-1

55661-33-1 Thiazol-2-ylmethanamine 2756507, athiazole compound, is more and more widely used in various.

General procedure: 5.1.5 2-(1-(4-Fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamide (7a) To a solution of 6a (2.00 g, 5.98 mmol), EDCI (1.50 g, 7.82 mmol) and iPr2NEt (2.67 mL, 15.64 mmol) in N,N-dimethylformamide (80 mL) was added HOBt (1.00 g, 7.40 mmol). The reaction mixture was stirred at ambient temperature for 15 min, followed by addition of 3-(aminomethyl)pyridine (0.73 mL, 7.16 mmol). After stirring for 17 h at ambient temperature, the reaction mixture was diluted with ethyl acetate (300 mL) and sequentially washed with water, saturated NaHCO3 solution, water and brine. The organic solution was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was crystallized from ethyl acetate and hexanes to yield 7a as an off-white solid (1.93 g, 76%), mp 178-180 C (ethyl acetate/hexanes); By a similar procedure as described for 7a, 7h was obtained as an off-white solid (0.17g, 66%). Mp 189-190C (ethyl acetate/hexanes); 1H NMR (300MHz, CDCl3) delta 8.25 (s, 1H), 7.74 (br s, 1H), 7.40-7.31 (m, 3H), 7.06-6.97 (m, 2H), 6.78 (t, J=5.4Hz, 1H), 4.97 (s, 2H), 4.92 (d, J=5.4Hz, 2H), 2.67 (s, 3H); MS (ES+) m/z 431.1 (M+1), 55661-33-1

55661-33-1 Thiazol-2-ylmethanamine 2756507, athiazole compound, is more and more widely used in various.

Reference£º
Article; Sun, Shaoyi; Zhang, Zaihui; Pokrovskaia, Natalia; Chowdhury, Sultan; Jia, Qi; Chang, Elaine; Khakh, Kuldip; Kwan, Rainbow; McLaren, David G.; Radomski, Chris C.; Ratkay, Leslie G.; Fu, Jianmin; Dales, Natalie A.; Winther, Michael D.; Bioorganic and Medicinal Chemistry; vol. 23; 3; (2015); p. 455 – 465;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Brief introduction of 55661-33-1

55661-33-1 Thiazol-2-ylmethanamine 2756507, athiazole compound, is more and more widely used in various.

55661-33-1,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.55661-33-1,Thiazol-2-ylmethanamine,as a common compound, the synthetic route is as follows.

Example 3; 2-(2-oxo-3,3-diphenylpyrrolidin-l-yl)-7V-(l,3-thiazol-2-ylmethyl)acetamide; N1-((ethylimino)methylene)-Lambda/3,Lambda/3-dimethylpropane-l ,3-diamine hydrochloride(0.049 g, 0.254 mmol) , 2-(2-oxo-3,3-diphenylpyrrolidin-l-yl)acetic acid (Example 1C, 0.050 g, 0.169 mmol) and thiazol-2-ylmethanamine (0.021 g, 0.186 mmol) were combined and stirred together in dichloromethane (0.5 mL) at room temperature. After stirring overnight, the reaction was loaded directly onto a SF 15- 12 silica gel column (Analogix, Burlington, WI), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow = 30 mL/minute). 1H NMR (300 MHz, CDCl3) delta ppm 7.69 (d, J= 3.3 Hz, 1 H), 7.19-7.38 (m, 11 H), 6.77 (t, J= 5.8 Hz, 1 H), 4.67 (d, J= 5.8 Hz, 2 H), 4.09 (s, 2 H), 3.53 (t, J= 6.5 Hz, 2 H), 2.84 (t, J= 6.5 Hz, 2H); MS (ESI+) m/z 392 (M+H)+.

55661-33-1 Thiazol-2-ylmethanamine 2756507, athiazole compound, is more and more widely used in various.

Reference£º
Patent; ABBOTT LABORATORIES; BHATIA, Pramila, A.; DOHERTY, George, A.; DRIZIN, Irene; MACK, Helmut; PERNER, Richard, J.; STEWART, Andrew, O.; ZHANG, Qing Wei; WO2010/39947; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica