- A 4-(o-chlorophenyl)-2-aminothiazole: Microwave assisted synthesis, spectral, thermal, XRD and biological studies
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A 4-(o-chlorophenyl)-2-aminothiazole (CPAT) has been synthesized by reacting o-chloroacetophenone, iodine and thiourea under microwave irradiation as a green chemistry approach. The reactions proceed selectively and within a couple of minutes giving high
- Rajmane,Ubale,Lawand,Nalawade,Karale,More
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- A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system
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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.
- Zhang, Qian,Wu, Jiefei,Pan, Zexi,Zhang, Wen,Zhou, Wei
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- COLLAGEN 1 TRANSLATION INHIBITORS AND METHODS OF USE THEREOF
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The present invention relates to novel collagen translation inhibitors 1, a composition, their preparation methods, and their uses for the treatment of fibrosis in particular, fibrosis of the lung, liver, kidney, cardiac and dermal fibrosis, IPF, wound he
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- Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas
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Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.
- Chen, Yuncan,Lv, Shan,Lai, Ruizhi,Xu, Yingying,Huang, Xin,Li, Jianglian,Lv, Guanghui,Wu, Yong
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p. 2555 - 2558
(2021/03/17)
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- Method for preparing 2-aminothiazole compound
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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.
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Paragraph 0048-0053
(2020/03/09)
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- Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors
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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.
- Dai, Weiyang,Samanta, Soma,Xue, Ding,Petrunak, Elyse M.,Stuckey, Jeanne A.,Han, Yanyan,Sun, Duxin,Wu, Yong,Neamati, Nouri
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p. 3068 - 3087
(2019/03/07)
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- Novel 1,3,5-triazine derivatives exert potent anti-cervical cancer effects by modulating Bax, Bcl2 and Caspases expression
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This study aimed to develop novel 1,3,5-triazine derivatives as potent anti-cervical cancer agents. The compounds were synthesized in short steps with an excellent yield and characterized via various spectroscopic and analytical methods. A structure–activity relationship study suggested that electron-withdrawing substituents showed greater anticancer activity than electron-donating groups. Compound 7p (p-fluoro) showed the highest activity against cervical cancer cells. In a nude mouse xenograft model inoculated with HeLa cells, 7p showed dose-dependent inhibition of cervical tumour growth. Histopathological examination of excised tumour-bearing tissues showed that 7p improved the microstructure in a dose-dependent manner. Compound 7p also increased the proportions of HeLa cells in G0/G1 and S-phase and significantly decreased that of G2/M-phase. The effects of 7p on C-caspase-3, C-caspase-9, Bcl-2 and Bax expression in HeLa cells were also determined.
- Wang, Xiwen,Yi, Yuexiong,Lv, Qiongying,Zhang, Juan,Wu, Kejia,Wu, Wanrong,Zhang, Wei
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p. 728 - 734
(2017/11/21)
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- Design and development of some thiazole-based flavanoids as novel antibacterial against pathogens causing surgical site infection for possible benefit in bone trauma via inhibition of DNA gyrase
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In this study, a novel class of hybrid thiazole-based flavanoid derivatives were synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR, mass and elemental analysis. These derivatives were evaluated for antibacterial activity for possible benefit in bone trauma via inhibition of DNA gyrase enzyme. Results suggested that compounds 9n, 9o, and 9p showed considerable inhibition of DNA gyrase with considerable activity against tested forty strains of Staphylococcus aureus clinical isolates. Moreover, compound 9n showed hydrogen bonding with LYS460 along with low binding free energy of ?4.36?kcal/mol against DNA gyrase enzyme. The hemolytic activity of the potent compounds showed mild to no activity together with excellent pharmacokinetics, suggesting to have a potential for the development of designed compounds as novel antibacterial agents.
- Zhao, Gang,Lan, Dengzhe,Qi, Guobao
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p. 778 - 790
(2017/11/15)
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- 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
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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.
- Gundala, Trivikram Reddy,Godugu, Kumar,Nallagondu, Chinna Gangi Reddy
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p. 1408 - 1416
(2017/10/23)
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- Discovery of novel N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides as potent RORγt inhibitors
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Novel series of N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides were discovered as potent retinoic acid receptor-related orphan receptor-gamma-t (RORγt) inhibitors. SAR studies of the RORγt HTS hit 6a led to identification of thiazole ketone amide 8h and thiophene ketone amide 9g with high binding affinity and inhibitory activity of Th17 cell differentiation. Compound 8h showed in vivo efficacy in both mouse experimental autoimmune encephalomyelitis (EAE) and collagen induced arthritis (CIA) models via oral administration.
- Wang, Yonghui,Cai, Wei,Zhang, Guifeng,Yang, Ting,Liu, Qian,Cheng, Yaobang,Zhou, Ling,Ma, Yingli,Cheng, Ziqiang,Lu, Sijie,Zhao, Yong-Gang,Zhang, Wei,Xiang, Zhijun,Wang, Shuai,Yang, Liuqing,Wu, Qianqian,Orband-Miller, Lisa A.,Xu, Yan,Zhang, Jing,Gao, Ruina,Huxdorf, Melanie,Xiang, Jia-Ning,Zhong, Zhong,Elliott, John D.,Leung, Stewart,Lin, Xichen
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supporting information
p. 692 - 702
(2014/01/23)
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- Synthesis and anticancer evaluation of 3-aryl-6-phenylimidazo[2,1-b]thiazoles
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A series of new 3,6-diphenylimidazo[2,1-b]thiazole derivatives (4a-l) are synthesized and evaluated for their anticancer activity. Some of the synthesized compounds have shown potent anti-proliferative activity against HeLa, MDA-MB-231, A549 and THP1 huma
- Koppireddi, Satish,Chilaka, Deepika Raj Kumari,Avula, Sreenivas,Komsani, Jayaram Reddy,Kotamraju, Srigiridhar,Yadla, Rambabu
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supporting information
p. 5428 - 5431
(2015/01/08)
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- Novel 2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamides as antioxidant and/or anti-inflammatory compounds
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A series of novel N-(4-aryl-1,3-thiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin- 5-yl)acetamides (4a-k) and N-(1,3-benzothiazol-2-yl)-2-(2,4-dioxo-1,3- thiazolidin-5-yl)acetamide derivatives (4l-o) are synthesized and evaluated for their anti-inflammatory and antioxidant activity (DPPH radical scavenging, superoxide anion scavenging, lipid peroxide inhibition, erythrocyte hemolytic inhibition). Compounds 4k and 4l have exhibited good antioxidant activity in four assays, while compounds 4c, 4d , 4m, 4n and 4o have shown good DPPH radical scavenging efficacy. Compounds 4a, 4h , 4i, 4k, 4m and 4n have possessed excellent anti-inflammatory activity. N-[4-(o-methoxyphenyl)-1,3-thiazol-2-yl]- 2-(2,4-dioxo-1,3-thiazolidin-5-yl) acetamide (4k) and N-(6-nitro-/methoxy-1,3- benzothiazol-2-yl)-2-(2,4-dioxo-1,3-thiazolidin-5-yl)acetamide (4m and 4n) have exhibited both antioxidant and anti-inflammatory activities.
- Koppireddi, Satish,Komsani, Jayaram Reddy,Avula, Sreenivas,Pombala, Sujitha,Vasamsetti, Satishbabu,Kotamraju, Srigiridhar,Yadla, Rambabu
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p. 305 - 313
(2013/10/01)
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- Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes
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Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-α. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 μM and a binding affinity for ap2 with the apparent Ki values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent.
- Xu, Qinyuan,Huang, Li,Liu, Juan,Ma, Liang,Chen, Tao,Chen, Jinying,Peng, Fei,Cao, Dong,Yang, Zhuang,Qiu, Neng,Qiu, Jingxiang,Wang, Guangcheng,Liang, Xiaolin,Peng, Aihua,Xiang, Mingli,Wei, Yuquan,Chen, Lijuan
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experimental part
p. 70 - 81
(2012/07/30)
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- COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS
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The present invention is directed to novel compounds of formula (I) and their use in treating metabolic diseases.
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Page/Page column 209
(2010/06/22)
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- Synthesis and antibacterial activity of bis[2-amino-4-phenyl-5-thiazolyl] disulfides
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Different dimeric disulfides, having the basic skeleton of bis[2-amino-4-phenyl-5-thiazolyl] disulfides were synthesized in a straightforward manner from acetophenones. 2-Amino-4-phenyl-1,3-thiazoles were prepared by the reaction of thiourea with substitu
- Siddiqui, Hamid Latif,Zia-Ur-Rehman, Muhammad,Ahmad, Naveed,Weaver, George William,Lucas, Paul David
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p. 1014 - 1017
(2008/02/13)
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- Synthesis and cytotoxic activity of certain new arylazothiazole containing compounds
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2-Amino-5-arylazo-4-(2-chlorophenyl)thiazoles (2a-e) were prepared by the coupling of aryldiazonium chlorides with 2-amino-4-(2-chlorophenyl) thiazole (1). The thioureas 3a-e were obtained by condensing the arylazothiazoles 2a-c with the appropriate isoth
- El-Meligie, Salwa,El-Awady, Raafat A.
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p. 1133 - 1138
(2007/10/03)
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- Studies of arylthiazole oxamates in relation to oral antiallergic activity
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25 arylthiazole oxamate derivatives were synthesized and examined for antiallergic activity in the rat passive cutaneous anaphylaxis assay. These compounds were prepared by treatment of the appropriate bromoacetophenone with thioureas to give arylaminothiazoles. Further condensation with alkyloxalyl chloride gave the arylthiazolyl oxamates. Several derivatives showed a 70% inhibition at 5 mg/kg p.o. p-Alkoxy substitution on the phenyl ring resulted in enhanced activity while N-alkyl substitution on the nitrogen amide function inhibited the activity. Ethyl-N-(4-p-methoxyphenyl)-2-thiazolyl oxamate (tioxamast, F-1865) was selected for clinical studies.
- Cousse,Mouzin,Bonnaud,Tarayre,Couzinier
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p. 1391 - 1393
(2007/10/02)
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