30709-67-2Relevant academic research and scientific papers
A novel synthesis of 2-imino-4-thiazolines via α-bromoketimines
De Kimpe, Norbert,Boelens, Mark,Declercq, Jean-Paul
, p. 3411 - 3424 (1993)
A novel straightforward synthesis of 2-imino-4-thiazolines has been performed by reaction of α-bromoketimines with potassium thiocyanate in acetonitrile. Contrary to other syntheses of these heterocycles, no side reactions were observed. The structural as
A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system
Zhang, Qian,Wu, Jiefei,Pan, Zexi,Zhang, Wen,Zhou, Wei
, p. 89 - 94 (2020/06/17)
A series of 2-aminothiazoles is prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus providing a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction.
Method for preparing 2-aminothiazole compound
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Paragraph 0120-0125, (2020/03/09)
The invention discloses a method for preparing a 2-aminothiazole compound. The method comprises the following steps: in an organic solvent, carrying out a condensation reaction on thiourea representedby a formula (II) and a ketone compound represented by a formula (III) at 50-120 DEG C for 6-24 h under the catalysis of elemental iodine, and after the reaction is finished, carrying out post-treatment on the reaction solution to obtain the 2-aminothiazole compound represented by a formula (I). According to the invention, the method has characteristics of cheap and easily available reaction rawmaterials, mild reaction conditions, simpleness, no requirement of transition metal catalysts and a stoichiometric halogenating reagents and cost reducing, and can be used for synthesizing a series of2-aminothiazole derivatives, and the prepared products can be used as important intermediates for synthesizing thiazole structure-containing drugs or bioactive compounds.
Synthesis and biological evaluation of 5-methyl-4-phenyl thiazole derivatives as anticancer agents
Evren, Asaf E.,Yurttas, Leyla,Ekselli, Bü?ra,Akalin-Ciftci, Gül?en
, p. 820 - 828 (2019/03/07)
New N-(5-methyl-4-phenylthiazol-2-yl)-2-(substituted thio)acetamides were synthesized and studied for their anticancer activity. The title compounds were procured by reacting 2-chloro-N-(5-methyl-4-phenylthiazol-2-yl)acetamide with some mercapto derivatives. The structural elucidation of the compounds was performed by 1H-NMR, 13C-NMR and LC-MS/MS spectral data and elemental analyses. The synthesized compounds were investigated for their antitumor activities against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell line for determining their selective cytotoxicity. 2-[(1-methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenylthiazol-2-yl)acetamide (4c) showed high selectivity, and whose IC50 value was determined as 23.30 ± 0.35 μM and >1000 μM against A549 human lung adenocarcinoma cells and NIH/3T3 mouse embryoblast cell lines, respectively. 2-[(1-Methyl-1H-imidazol-2-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4a) and 2-[(1-Methyl-1H-tetrazol-5-yl)thio]-N-(5-methyl-4-phenyl thiazol-2-yl)acetamide (4c) exhibited the highest apoptosis percentage among those tested, but not as high as the standard, cisplatin.
SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF NUCLEASES
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Page/Page column 14-15; 40; 57, (2019/11/12)
The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.
Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors
Dai, Weiyang,Samanta, Soma,Xue, Ding,Petrunak, Elyse M.,Stuckey, Jeanne A.,Han, Yanyan,Sun, Duxin,Wu, Yong,Neamati, Nouri
, p. 3068 - 3087 (2019/03/07)
Using reported glutathione S-transferase omega 1 (GSTO1-1) cocrystal structures, we designed and synthesized acrylamide-containing compounds that covalently bind to Cys32 on the catalytic site. Starting from a thiazole derivative 10 (GSTO1-1 IC50 = 0.6 μM), compound 18 was synthesized and cocrystallized with GSTO1. Modification on the amide moiety of hit compound 10 significantly increased the GSTO1-1 inhibitory potency. We solved the cocrystal structures of new derivatives, 37 and 44, bearing an amide side chain bound to GSTO1. These new structures showed a reorientation of the phenyl thiazole core of inhibitors, 37 and 44, when compared to 18. Guided by the cocrystal structure of GSTO1:44, analogue 49 was designed, resulting in the most potent GSTO1-1 inhibitor (IC50 = 0.22 ± 0.02 nM) known to date. We believe that our data will form the basis for future studies of developing GSTO1-1 as a new drug target for cancer therapy.
2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas
Shibasaki, Kaho,Togo, Hideo
, p. 2520 - 2527 (2019/04/04)
Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.
Synthesis and biological evaluation of novel thiazole- VX-809 hybrid derivatives as F508del correctors by QSAR-based filtering tools
Liessi, Nara,Cichero, Elena,Pesce, Emanuela,Arkel, Maria,Salis, Annalisa,Tomati, Valeria,Paccagnella, Matteo,Damonte, Gianluca,Tasso, Bruno,Galietta, Luis J.V.,Pedemonte, Nicoletta,Fossa, Paola,Millo, Enrico
, p. 179 - 200 (2017/12/28)
The most common CF mutation, F508del, impairs the processing and gating of CFTR protein. This deletion results in the improper folding of the protein and its degradation before it reaches the plasma membrane of epithelial cells. Present correctors, like VX809 only induce a partial rescue of the mutant protein. Our previous studies reported a class of compounds, called aminoarylthiazoles (AATs), featuring an interesting activity as correctors. Some of them show additive effect with VX809 indicating a different mechanism of action. In an attempt to construct more interesting molecules, it was thought to generate chemically hybrid compounds, blending a portion of VX809 merged to the thiazole scaffold. This approach was guided by the development of QSAR analyses, which were performed based on the F508del correctors so far disclosed in the literature. This strategy was aimed at exploring the key requirements turning in the corrector ability of the collected derivatives and allowed us to derive a predictive model guiding for the synthesis of novel hybrids as promising correctors. The new molecules were tested in functional and biochemical assays on bronchial CFBE41o-cells expressing F508del-CFTR showing a promising corrector activity.
Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)
Ma, Chunhua,Miao, Yuqi,Zhao, Minghao,Wu, Ping,Zhou, Jianglu,Li, Zhi,Xie, Xilei,Zhang, Wei
, p. 3602 - 3607 (2018/05/26)
An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.
Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach
Gundala, Trivikram Reddy,Godugu, Kumar,Nallagondu, Chinna Gangi Reddy
, p. 1408 - 1416 (2017/10/23)
An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.
