5330-67-6Relevant academic research and scientific papers
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
Kalhor, Mehdi,Zarnegar, Zohre
, p. 519 - 540 (2021/12/03)
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.]
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.
Novel synthesis of 2-Aminothiazoles via Fe(III)-Iodine-catalyzed Hantzsch-type condensation
Ujwaldev, Sankuviruthiyil M.,Harry, Nissy Ann,Neetha, Mohan,Anilkumar, Gopinathan
supporting information, p. 646 - 653 (2020/10/20)
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.
Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas
Chen, Yuncan,Lv, Shan,Lai, Ruizhi,Xu, Yingying,Huang, Xin,Li, Jianglian,Lv, Guanghui,Wu, Yong
, p. 2555 - 2558 (2021/03/17)
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.
Structure-activity relationship studies in substituted sulfamoyl benzamidothiazoles that prolong NF-κB activation
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.
, (2021/07/19)
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.
Method for preparing 2-aminothiazole compound
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Paragraph 0084-0089, (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.
Asparagine functionalized Al2O3 nanoparticle as a superior heterogeneous organocatalyst in the synthesis of 2-aminothiazoles
Zarnegar, Zohre,Shokrani, Zahra,Safari, Javad
, p. 143 - 152 (2019/03/14)
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.
COMPOUNDS AND USES THEREOF
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Page/Page column 100, (2019/08/26)
The present disclosure features compounds useful for the treatment of BAF complex-related disorders.
Novel 1,3,5-triazine derivatives exert potent anti-cervical cancer effects by modulating Bax, Bcl2 and Caspases expression
Wang, Xiwen,Yi, Yuexiong,Lv, Qiongying,Zhang, Juan,Wu, Kejia,Wu, Wanrong,Zhang, Wei
, p. 728 - 734 (2017/11/21)
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.
C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay
Zarnegar, Zohre,Alizadeh, Roghayeh,Ahmadzadeh, Majid,Safari, Javad
, p. 58 - 65 (2017/05/12)
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.
