5153-67-3Relevant academic research and scientific papers
Investigation of regioselectivity in the synthesis of spiro [pyrrolidine-2,3′-oxindoles] by use of the Huisgen reaction
Chen, Gang,Miao, Yan-Qing,Zhou, Rui,Zhang, Li,Zhang, Jie,Hao, Xiao-Jiang
, p. 2445 - 2450 (2013)
The Huisgen reaction has been used to synthesize five-membered heterocyclic compounds in high yield and with high regio and stereoselectivity. In the synthesis of spiro [pyrrolidine-2,3′-oxindole] derivatives from isatin, α-amino acids, and (E)-β-phenyl nitroolefins, two regioisomers were obtained in each reaction. The regioselectivity of the major product was found to be different from that in reported work, and was investigated at the B3LYP/6-311G*level of theory. On the basis of this new finding, several conditions, for example molar ratio, solvent, and temperature, which affect the regioselectivity of this reaction were investigated; the results obtained are discussed. It was found that the regioselectivity of this reaction was affected by solvent and temperature, irrespective of the ratio of the reactants. Low temperature and high solvent polarity leads to high regioselectivity, and protic solvents result in higher yield and regioselectivity. These results are of benefit for regioselective synthesis of some compounds.
Synthesis and catalytic activity of novel Ni-N complexes1
Mei,Tao,Long,Ming,Liang,Rong
, p. 567 - 572 (2012)
A series of nickel complexes with 1,3-xylylenediamine, 1,2-diaminobenzene and 1,2-aminobenzylamine were first synthesized and characterized. The reaction of these amines with Ni(OAc)2 · 4H2O and NiCl 2 · 6H2O in methanol or tetrahydrofuran resulted in the production of four novel nickel complexes I, II, III, and IV. The structure of each complex was determined by X-ray diffraction analysis. Each complex was also characterized using elemental analysis, 1H NMR and IR. The complexes were then used to catalyze the Henry reaction, and good catalytic results (65-99%) were achieved. The catalytic activity of the complexes was determined by 1H NMR.
Anti-inflammatory potential of 1-nitro-2-phenylethylene
Sugimoto, Michelle A.,Da Silva, Márcia de Jesus Amazonas,Brito, Larissa Froede,Borges, Rosivaldo dos Santos,Amaral, Flávio Almeida,Boleti, Ana Paula de Araujo,Ordo?ez, Maritza Echevarria,Tavares, Jose Carlos,Sousa, Lirlandia Pires,Lima, Emerson Silva
, (2017)
Inflammation is a reaction of the host to infectious or sterile stimuli and has the physiological purpose of restoring tissue homeostasis. However, uncontrolled or unresolved inflammation can lead to tissue damage, giving rise to a plethora of chronic inflammatory diseases, including metabolic syndrome and autoimmunity pathologies with eventual loss of organ function. Beta-nitrostyrene and its derivatives are known to have several biological activities, including anti-edema, vasorelaxant, antiplatelet, anti-inflammatory, and anticancer. However, few studies have been carried out regarding the anti-inflammatory effects of this class of compounds. Thereby, the aim of this study was to evaluate the anti-inflammatory activity of 1-nitro-2-phenylethene (NPe) using in vitro and in vivo assays. Firstly, the potential anti-inflammatory activity of NPe was evaluated by measuring TNF-α produced by human macrophages stimulated with lipopolysaccharide (LPS). NPe at non-toxic doses opposed the inflammatory effects induced by LPS stimulation, namely production of the inflammatory cytokine TNF-α and activation of NF-κB and ERK pathways (evaluated by phosphorylation of inhibitor of kappa B-alpha [IκB-α] and extracellular signal-regulated kinase 1/2 [ERK1/2], respectively). In a well-established model of acute pleurisy, pretreatment of LPS-challenged mice with NPe reduced neutrophil accumulation in the pleural cavity. This anti-inflammatory effect was associated with reduced activation of NF-κB and ERK1/2 pathways in NPe treated mice as compared to untreated animals. Notably, NPe was as effective as dexamethasone in both, reducing neutrophil accumulation and inhibiting ERK1/2 and IκB-α phosphorylation. Taken together, the results suggest a potential anti-inflammatory activity for NPe via inhibition of ERK1/2 and NF-κB pathways on leukocytes.
Mesoporous silica with site-isolated amine and phosphotungstic acid groups: A solid catalyst with tunable antagonistic functions for one-pot tandem reactions
Shiju, N. Raveendran,Alberts, Albert H.,Khalid, Syed,Brown, David R.,Rothenberg, Gadi
, p. 9615 - 9619 (2011)
Coniuga et impera: A bifunctional solid catalyst is prepared by combining acid and base functions on mesoporous silica supports (see picture). The co-existence of these functions is shown by a two-step reaction sequence in one pot. Excellent product yields, which cannot be obtained by separated acid and base functions in one pot, show the validity of our concept. Copyright
N-Heterocyclic Iod(az)olium Salts – Potent Halogen-Bond Donors in Organocatalysis
Boelke, Andreas,Kuczmera, Thomas J.,Lork, Enno,Nachtsheim, Boris J.
supporting information, p. 13128 - 13134 (2021/08/09)
This article describes the application of N-heterocyclic iod(az)olium salts (NHISs) as highly reactive organocatalysts. A variety of mono- and dicationic NHISs are described and utilized as potent XB-donors in halogen-bond catalysis. They were benchmarked in seven diverse test reactions in which the activation of carbon- and metal-chloride bonds as well as carbonyl and nitro groups was achieved. N-methylated dicationic NHISs rendered the highest reactivity in all investigated catalytic applications with reactivities even higher than all previously described monodentate XB-donors based on iodine(I) and (III) and the strong Lewis acid BF3.
Design, Synthesis, and Biological Evaluation of Organic Nitrite (NO 2-) Donors as Potential Anticerebral Ischemia Agents
Wu, Jianbing,Yin, Wei,Huang, Zhangjian,Zhang, Yinqiu,Jia, Jian,Cheng, Huimin,Kang, Fenghua,Huang, Kai,Sun, Tao,Tian, Jide,Xu, Xiaojun,Zhang, Yihua
, p. 10919 - 10933 (2021/08/16)
The treatment of ischemic stroke (IS) remains a big challenge in clinics, and it is urgently needed to develop novel, safe, and effective medicines against IS. Here, we report the design, synthesis, and biological evaluation of organic NO2- donors as potential agents for the treatment of IS. The representative compound 4a was able to slowly generate low concentrations of NO2- by reaction with a thiol-containing nucleophile, and the NO2- was selectively converted into NO under ischemic/hypoxia conditions to protect primary rat neurons from oxygen-glucose deprivation and recovery (OGD/R)-induced cytotoxicity by enhancing the Nrf2 signaling and activating the NO/cGMP/PKG pathway. Treatment with 4a at 2 h before or after ischemia mitigated the ischemia/reperfusion-induced brain injury in middle cerebral artery occlusion (MCAO) rats by producing NO and enhancing Nrf2 signaling. Furthermore, 4a significantly promoted endothelial cell proliferation and angiogenesis within the ischemic penumbra. Our findings suggest that this type of NO2- donors, like 4a, may be valuable to fight IS and other ischemic diseases.
Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles
Kumar, Rakesh,Banerjee, Prabal
, p. 16104 - 16113 (2021/11/18)
Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction ofN-heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins. This electrosynthetic methodology indulges a straightforward and facile approach for the construction of substituted pyrrolidines.
Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"
Gao, Fengyun,Guo, Yifei,Sun, Mengmeng,Wang, Yalan,Yang, Changyan,Wang, Yuqiang,Wang, Kairong,Yan, Wenjin
supporting information, p. 2584 - 2589 (2021/04/13)
We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.
Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis
Bai, Rongxian,Gao, Feng,Gu, Yanlong,Li, Minghao
supporting information, p. 7499 - 7505 (2021/10/12)
Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.
A noncovalent hybrid of [Pd(phen)(OAc)2] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine
Pal, Mrityunjoy,Musib, Dulal,Pal, Maynak,Rana, Gopal,Bag, Gobinda,Dutta, Subrata,Roy, Mithun
supporting information, p. 5072 - 5076 (2021/06/21)
We developed a novel Pd-catalysed enantioselective synthesis of C-N bonds using the chiral scaffold of DNA. The non-covalently linked [Pd(phen)(OAc)2] with st-DNA catalysed the Markonicov hydroamination of β-nitrostyrene with methoxyamine for the first time with >75% enantiomeric excess (ee) in an aqueous buffer (pH 7.4) at room temperature.
