Xi:Irritant;10389-51-2Relevant articles and documents
Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics
Fors, Brett P.,Buchwald, Stephen L.
, p. 12898 - 12899 (2009)
(Chemical Equation Presented) An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent
Exploring the influence of designer surfactant hydrophobicity in key C–C/C–N bond forming reactions
Reddy, Singarajanahalli Mundarinti Krishna,Kothandapani, Jagatheeswaran,Sengan, Megarajan,Veerappan, Anbazhagan,Selva Ganesan, Subramaniapillai
, p. 80 - 86 (2019)
Designer micellar medium was explored for the transformation of diverse anilines to the corresponding densely substituted biologically relevant skatole derivatives in an aqueous medium via 5-exo-trig cyclization reaction. The scope of the reaction was extended to intermolecular Csp2-Csp2 and Csp2-N bond forming reactions in water. Systematic investigations revealed that altering hydrophobicity of surfactant influences the yield of both C–C and C–N bond forming reactions in water.
A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water
Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat
, p. 10645 - 10660 (2020)
A novel magnetically recyclable bimetallic catalyst was prepared by anchoring imidazolium moiety and PEG chains on Fe3O4 NPs and named as Fe3O4?PEG/Cu-Co. It was found to be a powerful catalyst for the Sonogashira, Suzuki, and C-N cross-coupling reactions in water as a green solvent without the need for any external base. Fe3O4?PEG/Cu-Co was well characterized with FT-IR, FE-SEM, TEM, VSM, EDX, ICP, UV-visible, CV, and XPS analyses. Optimum ranges of parameters such as time, temperature, and amount of catalyst were investigated by Design-Expert 10.0.7 software for C-C Suzuki, Sonogashira, and C-N cross-coupling reactions to find the optimum conditions. The catalyst was compatible with a variety of aryl halides and N-arenes and gave favorable coupling products with good to high yields for all of them. Hot filtration and Hg poisoning tests involving the nanocatalyst revealed the stability, low metal leaching, and heterogeneous nature of the catalyst. Reaction mechanisms were proposed by study of the UV-visible spectra in situ as well as hydroquinone tests during the progress of reactions. In situ XPS analysis was also used to study the reaction mechanism. To prove the synergistic performance of Co and Cu in the catalyst, its various homologues were synthesized and applied to a model reaction separately, and then their catalytic activities were investigated. Finally, the catalyst could be recovered from the reaction mixture simply, and reused for several cycles with a minimum loss in catalytic activity and performance.
Chitosan-Supported Ni particles: An Efficient Nanocatalyst for Direct Amination of Phenols
Hajipour, Abdol R.,Abolfathi, Parisa
, (2018)
A practical method for the direct amination of phenols using 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient promotor for the activation of phenols in the presence of an efficient and recyclable heterogeneous catalyst prepared by immobilization of nickel particles on triazole modified chitosan is described. This heterogeneous catalyst has demonstrated a promising activity for the conversion of phenolic compounds to their corresponding amine under mild conditions. Moreover, the obtained catalyst can be reused in five consecutive runs with consistent catalytic activity.
First-in-class DAPK1/CSF1R dual inhibitors: Discovery of 3,5-dimethoxy-N-(4-(4-methoxyphenoxy)-2-((6-morpholinopyridin-3-yl)amino)pyrimidin-5-yl)benzamide as a potential anti-tauopathies agent
Farag, Ahmed Karam,Hassan, Ahmed H.E.,Jeong, Hyeanjeong,Kwon, Youngji,Choi, Jin Gyu,Oh, Myung Sook,Park, Ki Duk,Kim, Yun Kyung,Roh, Eun Joo
, p. 161 - 175 (2019)
Kinase irregularity has been correlated with several complex neurodegenerative tauopathies. Development of selective inhibitors of these kinases might afford promising anti-tauopathy therapies. While DAPK1 inhibitors halt the formation of tau aggregates and counteract neuronal death, CSF1R inhibitors could alleviate the tauopathies-associated neuroinflammation. Herein, we report the design, synthesis, biological evaluation, mechanistic study, and molecular docking study of novel CSF1R/DAPK1 dual inhibitors as multifunctional molecules inhibiting the formation of tau aggregates and neuroinflammation. Compound 3l, the most potent DAPK1 inhibitor in the in vitro kinase assay (IC50 = 1.25 μM) was the most effective tau aggregates formation inhibitor in the cellular assay (IC50 = 5.0 μM). Also, compound 3l elicited potent inhibition of CSF1R in the in vitro kinase assay (IC50 = 0.15 μM) and promising inhibition of nitric oxide production in LPS-induced BV-2 cells (55% inhibition at 10 μM concentration). Kinase profiling and hERG binding assay anticipated the absence of off-target toxicities while the PAMPA-BBB assay predicted potentially high BBB permeability. The mechanistic study and selectivity profile suggest compound 3l as a non-ATP-competitive DAPK1 inhibitor and an ATP-competitive CSF1R inhibitor while the in silico calculations illustrated binding of compound 3l to the substrate-binding site of DAPK1. Hence, compound 3l might act as a protein-protein interaction inhibitor by hindering DAPK1 kinase reaction through preventing the binding of DAPK1 substrates.
Controlled synthesis of water-dispersible faceted crystalline copper nanoparticles and their catalytic properties
Wang, Yanfei,Biradar, Ankush V.,Wang, Gang,Sharma, Krishna K.,Duncan, Cole T.,Rangan, Sylvie,Asefa, Tewodros
, p. 10735 - 10743 (2010)
We report a solution-phase synthetic route to copper nanoparticles with controllable size and shape. The synthesis of the nanoparticles is achieved by the reduction of copper(II) salt in aqueous solution with hydrazine under air atmosphere in the presence of poly(acrylic acid) (PAA) as capping agent. The results suggest that the pH plays a key role for the formation of pure copper nanoparticles, whereas the concentration of PAA is important for controlling the size and geometric shape of the nanoparticles. The average size of the copper nanoparticles can be varied from 30 to 80 nm, depending on the concentration of PAA. With a moderate amount of PAA, faceted crystalline copper nanoparticles are obtained. The as-synthesized copper nanoparticles appear red in color and are stable for weeks, as confirmed by UV/Vis and X-ray photoemission (XPS) spectroscopy. The faceted crystalline copper nanoparticles serve as an effective catalyst for N-arylation of heterocycles, such as the C-N coupling reaction between p-nitrobenzyl chloride and morpholine producing 4-(4-nitrophenyl) morpholine in an excellent yield under mild reaction conditions. Furthermore, the nanoparticles are proven to be versatile as they also effectively catalyze the three-component, one-pot Mannich reaction between p-substituted benzaldehyde, aniline, and acetophenone affording a 100% conversion of the limiting reactant (aniline).
Formation of dispersed palladium-nickel bimetallic nanoparticles in microemulsions: Synthesis, characterization, and their use as efficient heterogeneous recyclable catalysts for the amination reactions of aryl chlorides under mild conditions
Heshmatpour, Felora,Abazari, Reza
, p. 55815 - 55826 (2014)
A simple method for preparing spherical palladium-nickel bimetallic nanoparticles with a molar ratio of 1.0 (Pd0.5-Ni0.5 B-NPs) has been adopted using a water-in-oil microemulsion system of water/aerosol-OT/ isooctane at room temperature. The morphology, size, structure, and elemental composition of these particles as the superior catalyst were characterized by field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), energy dispersive analysis using X-rays (EDAX), and X-ray fluorescence (XRF) analyses. The effects of the reaction parameters on the Buchwald-Hartwig amination reaction yield in the presence of these NPs as catalyst have been screened and the results are evaluated by using chlorobenzene and morpholine as a model reaction. Initially, differences in the catalytic properties of some synthesized NPs have been compared. In this context, Pd-Ni B-NPs with the molar ratio of 1 : 1 (Pd/Ni = 1) showed the highest catalytic activity for this reaction. The Pd0.5-Ni0.5 B-NPs are stable and the leaching of catalyst in solution is very low. Therefore, they has been employed as efficient catalysts in the C-N coupling reaction. Finally, a mechanism for an amination reaction on the Pd/Ni catalyst surface was proposed.
An integrated flow and microwave approach to a broad spectrum protein kinase inhibitor
Russell, Cecilia,Lin, Andrew J. S.,Hains, Peter,Simone, Michela I.,Robinson, Phillip J.,Mccluskey, Adam
, p. 93433 - 93437 (2015)
The protein kinase inhibitor CTx-0152960 (6, 2-((5-chloro-2-((4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), and the piperazinyl analogue, CTx-0294885 (7, 2-((5-chloro-2-((4-piperazin-1-ylphenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), were prepared using a hybrid flow and microwave approach. The use of flow chemistry approaches avoided the need for Boc-protection of piperidine in the key SNAr coupling with 1-fluoro-4-nitrobenzene. Microwave coupling of 4-morphilinoaniline 8 and 4-(piperazine-1-yl)aniline 9 with 2-(2,5-dichloropyrimidine-4-ylamino)-N-methylbenzamide 10, proved to be the most efficacious route to the target analogues 6 and 7. This hybrid methodology reduced the number of synthetic steps, gave enhanced overall yields and increased atom economy through step reduction and minimal requirement for chromatographic purification, relative to the original batch synthesis approach.
Synthesis of tertiary aryl amines of various aryl halides and secondary amines using ortho-palladated complex of tribenzylamine
Hajipour, Abdol R.,Dordahan, Fatemeh,Rafiee, Fatemeh
, p. 704 - 706 (2013)
The activity of dimeric [Pd{C6H4(CH 2N(CH2Ph)2)} (μ-Br)]2 complex as an efficient, air- and moisture-tolerant catalyst was investigated in amination reactions of various aryl halides with secondary amines. Substituted tertiary aryl amines were produced in excellent yields and short reaction times using catalytic amounts of this dimeric complex in DMSO at 120°C. Copyright
Synthesis and biological evaluation of some novel dithiocarbamate derivatives
Salik, Begüm Nurpelin,?zkay, Yusuf,Demir ?zkay, ümide,Karaca Gener, Hülya
, (2014)
18 novel dithiocarbamate derivatives were synthesized in order to investigate their inhibitory potency on acetylcholinesterase enzyme and antimicrobial activity. Structures of the synthesized compounds were elucidated by spectral data and elemental analyses. The synthesized compounds showed low enzyme inhibitory activity. However, they displayed good antimicrobial activity profile. Antibacterial activity of compounds 4a, 4e, and 4p (MIC = 25 g/mL) was equal to that of chloramphenicol against Klebsiella pneumoniae (ATCC 700603) and Escherichia coli (ATCC 35218). Most of the compounds exhibited notable antifungal activity against Candida albicans (ATCC 10231), Candida glabrata (ATCC 90030), Candida krusei (ATCC 6258), and Candida parapsilosis (ATCC 7330). Moreover, compound 4a, which carries piperidin-1-yl supstituent and dimethylthiocarbamoyl side chain as variable group, showed twofold better anticandidal effect against all Candida species than reference drug ketoconazole.
