- 1-Methylimidazolium ionic liquid supported on Ni@zeolite-Y: fabrication and performance as a novel multi-functional nanocatalyst for one-pot synthesis of 2-aminothiazoles and 2-aryl benzimidazoles
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In the present study, 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride-supported Ni@zeolite-Y-based nanoporous materials (Ni@zeolite-Im-IL) were synthesized and their structures were confirmed using different characterization techniques such as FT-IR, FE-SEM, EDX, XRD, BET and TGA-DTG analyses. In order to synthesize this multi-functional nano-system, zeolite-NaY was modified first, with exchanged Ni2+ ions and 3-chloropropyltriethoxysilane (CPTES) as a coupling reagent and then functionalized to imidazolium chloride ionic liquid by N-methylimidazole. New multi-functional nano-material of Ni@zeolite-Im-IL demonstrated high activity in the catalytic synthesis of 2-aminothiazoles 3a–l by one-pot reaction of methylcarbonyls, thiourea and iodine at 80?°C in DMSO with good to excellent yields (85–98%). Also, the catalytic synthesis of 2-aryl benzimidazoles, 6a–m was performed by the condensational reaction of o-arylendiamine and aromatic aldehydes in EtOH at room temperature with excellent yields (90–98%). Advantages of this efficient synthetic strategy include higher purity and shorter reaction time, excellent yield, easy isolation of products, the good stability, activity and feasible reusability of the metallic ionic liquid nanocatalyst. These benefits have made this method more compatible with the principles of green chemistry. Graphical abstract: [Figure not available: see fulltext.]
- Kalhor, Mehdi,Zarnegar, Zohre
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p. 519 - 540
(2021/12/03)
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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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- Structure-activity relationship studies in substituted sulfamoyl benzamidothiazoles that prolong NF-κB activation
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In the face of emerging infectious diseases, there remains an unmet need for vaccine development where adjuvants that enhance immune responses to pathogenic antigens are highly desired. Using high-throughput screens with a cell-based nuclear factor κB (NF-κB) reporter assay, we identified a sulfamoyl benzamidothiazole bearing compound 1 that demonstrated a sustained activation of NF-κB after a primary stimulus with a Toll-like receptor (TLR)-4 agonist, lipopolysaccharide (LPS). Here, we explore systematic structure–activity relationship (SAR) studies on compound 1 that indicated the sites on the scaffold that tolerated modification and yielded more potent compounds compared to 1. The selected analogs enhanced release of immunostimulatory cytokines in the human monocytic cell line THP-1 cells and murine primary dendritic cells. In murine vaccination studies, select compounds were used as co-adjuvants in combination with the Food and Drug Administration approved TLR-4 agonistic adjuvant, monophosphoryl lipid A (MPLA) that showed significant enhancement in antigen-specific antibody titers compared to MPLA alone. Additionally, our SAR studies led to identification of a photoaffinity probe which will aid the target identification and mechanism of action studies in the future.
- Shukla, Nikunj M.,Chan, Michael,Lao, Fitzgerald S.,Chu, Paul J.,Belsuzarri, Masiel,Yao, Shiyin,Nan, Jason,Sato-Kaneko, Fumi,Saito, Tetsuya,Hayashi, Tomoko,Corr, Maripat,Carson, Dennis A.,Cottam, Howard B.
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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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- Novel synthesis of 2-Aminothiazoles via Fe(III)-Iodine-catalyzed Hantzsch-type condensation
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A novel iron-iodine catalyzed one pot synthesis of 2-aminothiazoles from methyl aryl ketones and thiourea is demonstrated. This protocol can be considered as a catalyzed version of the classical Hantzsch aminothiazole synthesis as it enables the in situ generation of α-iodoketones in the reaction medium using catalytic amount of iodine leading to Hantzsch condensation with thiourea. The supply of iodine for multiple catalytic cycles is ensured by using catalytic amounts of iron as it enables iodide to iodine oxidation. The generality of this protocol is also well established in this manuscript by synthesizing a variety of 2-aminothiazoles from different ketones and thiourea.
- Ujwaldev, Sankuviruthiyil M.,Harry, Nissy Ann,Neetha, Mohan,Anilkumar, Gopinathan
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supporting information
p. 646 - 653
(2020/10/20)
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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 0084-0089
(2020/03/09)
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- Asparagine functionalized Al2O3 nanoparticle as a superior heterogeneous organocatalyst in the synthesis of 2-aminothiazoles
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Asparagine functionalized aluminum oxide nanoparticles (Asp-Al2O3) have been prepared by a two-step procedure involving the grafting of Al2O3 with 3-chloropropyltrimethoxysilane (CPTMS) and subsequent organofunctionalization using asparagine amino acid. It is shown that Asp-Al2O3 exhibits as an active nanocatalyst for the preparation of 2-aminothiazoles is achieved by one-pot reaction of methylcarbonyls, thiourea and iodine. The structure of Asp-Al2O3 was characterized by fourier transform infrared radiation (FT-TR), thermal gravimetric analysis (TGA), X-ray diffraction (XRD), scanning electron microscopic (SEM), and energy-dispersive analysis of X-ray (EDAX) analyses. Advantages of this modified methodology include higher purity and excellent yield of products, greener and cleaner conditions, easy isolation of products and convenient manipulation. Moreover, immobilization of organocatalysts on the Al2O3 surface are stable under the catalytic reaction conditions resulting their efficient reuse.
- Zarnegar, Zohre,Shokrani, Zahra,Safari, Javad
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p. 143 - 152
(2019/03/14)
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- COMPOUNDS AND USES THEREOF
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The present disclosure features compounds useful for the treatment of BAF complex-related disorders.
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Page/Page column 100
(2019/08/26)
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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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- C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay
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In the current protocol, amine functionalized montmorillonite K10 nanoclay (NH2-MMT) was applied to catalyze the formation of C[sbnd]N bonds in the synthesis of azines and 2-aminothiazoles at room temperature. In comparison with the current methods of C[sbnd]N bond formation, this approach displays specific advantages include atom economy, clean conversion, design for energy efficiency, the use of nontoxic and heterogeneous catalyst, higher purity and yields, safer solvent and reagents for this organic transformation.
- Zarnegar, Zohre,Alizadeh, Roghayeh,Ahmadzadeh, Majid,Safari, Javad
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- Nanostarch: a novel and green catalyst for synthesis of 2-aminothiazoles
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Abstract: In this work, starch nanoparticles as a green and cheap catalyst were obtained based on the precipitation of amorphous starch in ethanol. It was found that starch nanoparticles are efficient catalyst for the synthesis of 2-aminothiazoles using methylcarbonyl compounds and thiourea as precursors. The use of green and biodegradable nanostarch makes this present methodology quite simple, shorter reaction times and milder conditions, and more convenient and economically viable compared to catalyzed methods reported in the literature. Graphical abstract: [Figure not available: see fulltext.]
- Safari, Javad,Sadeghi, Masoud
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p. 745 - 749
(2017/03/17)
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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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- Magnetic carbon nanotube-supported imidazolium cation-based ionic liquid as a highly stable nanocatalyst for the synthesis of 2-aminothiazoles
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Magnetic carbon nanotube-supported imidazolium ionic liquid (CNT-Fe3O4-IL) was synthesized and investigated using various characterization techniques, including Fourier transform infrared and Raman spectroscopies, X-ray diffraction, vibrating sample magnetometry, scanning and transmission electron microscopies, and thermogravimetric and differential thermal analyses. In order to synthesize the CNT-Fe3O4-IL nanocomposites, Fe3O4-decorated multi-walled CNTs were modified with 1-methyl-3-(3-trimethoxysilylpropyl)-1H-imidazol-3-ium chloride. This catalytic system was found to be a highly stable, active, reusable and solid-phase catalyst for the synthesis of 2-aminothiazoles via the one-pot reaction of ketone, thiourea and N-bromosuccinimide under mild conditions. Immobilized magnetic ionic liquid catalysis combines the advantages of ionic liquid media with magnetic solid support nanomaterials which enables the application of nanotechnology and green chemistry in chemical processes. Copyright
- Zarnegar, Zohre,Safari, Javad
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p. 1043 - 1049
(2016/11/23)
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- Nanochitosan: A biopolymer catalytic system for the synthesis of 2-aminothiazoles
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A convenient and efficient method is described for the synthesis of 2-aminothiazoles by one-pot reaction of ketone and thiourea using chitosan nanoparticles under mild condition. Nanochitosan was used as a biodegradable and green catalyst for this reaction in satisfactory yields. The attractive advantages of the present process include easy isolation of products, milder and cleaner conditions, higher purity and yields and easier work-up procedure.
- Safari, Javad,Abedi-Jazini, Zahra,Zarnegar, Zohre,Sadeghi, Masoud
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p. 108 - 112
(2016/02/05)
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- Synthesis of 2-aminothiazoles from methylcarbonyl compounds using a Fe3O4 nanoparticle-: N -halo reagent catalytic system
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An efficient protocol is developed for the synthesis of 2-aminothiazoles from unfunctionalized methylcarbonyl compounds using Fe3O4 nanoparticle-N-halo reagent catalytic systems. 1,3-dichloro-5,5-dimethylhydantoin (DCDMH), N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) as N-halo reagents were explored and the best results were obtained for DCDMH. Fe3O4 nanoparticle-DCDMH as an active, reusable, excellent, highly stable magnetic catalyst was used in this process. Advantages of this efficient method include greener and cleaner conditions, shorter reaction time, excellent yield of products, easy separation using a simple external magnetic field, low cost and operational simplicity.
- Sadeghi, Masoud,Safari, Javad,Zarnegar, Zohre
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p. 64749 - 64755
(2016/07/21)
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- Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles
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An efficient one-pot synthesis of 2-aminothiazoles from methylcarbonyl and thiourea has been developed using montmorillonite-K10 as a catalyst at 80?°C in DMSO medium. A plausible mechanism is proposed in which α-iodomethylcarbonyls are formed via methylcarbonyls as raw material using iodine as iodination reagent.
- Safari, Javad,Sadeghi, Masoud
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p. 8175 - 8183
(2016/11/25)
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- Synthesis and biological evaluation of N-(4-phenylthiazol-2-yl)cinnamamide derivatives as novel potential anti-tumor agents
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In this study, a series of novel N-(4-phenylthiazol-2-yl)cinnamamide derivatives (7a-8n) were synthesized and evaluated for their anti-proliferative activities in vitro by MTT assay and a possible antitumor mechanism was also explored. SAR analysis showed that steric effects played an important role on the anti-tumor activity. The most potent analogue 8f showed excellent inhibitions on the K562, Bel7402, A549 and Jurkat cells ranging from sub-micromolar to nanomolar concentration. Compound 8f inhibited Jurkat cells with an IC50 value of 0.035 μM with no apparent toxicity in different non-cancerous cells. Furthermore, it was suggested that the possible mechanism of 8f might be associated with inducing cancer cell apoptosis following flow cytometer analysis and Hoechst 33358 staining assays.
- Luo, Yong,Zhu, Yongxia,Ran, Kai,Liu, Zhihao,Wang, Ningyu,Feng, Qiang,Zeng, Jun,Zhang, Lidan,He, Bing,Ye, Tinghong,Zhu, Shirui,Qiu, Xiaolong,Yu, Luoting
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p. 1036 - 1042
(2015/06/25)
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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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- MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-κB ACTIVITY AND USE THEREOF
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Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including inflammatory and immune diseases, obesity and diabetes having the structure o
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Page/Page column 76
(2008/12/05)
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