7182-99-2Relevant articles and documents
Tert-Butyl Hydroperoxide-Mediated Oxo-Sulfonylation of 2 H-Indazoles with Sulfinic Acid toward Indazol-3(2 H)-ones
Ghosh, Payel,Mondal, Susmita,Hajra, Alakananda
supporting information, p. 1086 - 1090 (2020/02/04)
A new and efficient oxo-sulfonylation protocol has been established for the synthesis of N-sulfonylated indazolones employing sulfinic acid as a sulfonylating agent using tert-butyl hydroperoxide (TBHP) under ambient air. A series of structurally diverse 1-sulfonylindazol-3(2H)-one derivatives were obtained in good yields. A radical reaction mechanism has been proposed for this transformation.
Discovery of a benzenesulfonamide-based dual inhibitor of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase that favorably modulates lipid mediator biosynthesis in inflammation
Cheung, Sun-Yee,Werner, Markus,Esposito, Lucia,Troisi, Fabiana,Cantone, Vincenza,Liening, Stefanie,K?nig, Stefanie,Gerstmeier, Jana,Koeberle, Andreas,Bilancia, Rossella,Rizza, Roberta,Rossi, Antonietta,Roviezzo, Fiorentina,Temml, Veronika,Schuster, Daniela,Stuppner, Hermann,Schubert-Zsilavecz, Manfred,Werz, Oliver,Hanke, Thomas,Pace, Simona
supporting information, p. 815 - 830 (2018/07/29)
Leukotrienes (LTs) and prostaglandin (PG)E2, produced by 5-lipoxygenase (5-LO) and microsomal prostaglandin E2 synthase-1 (mPGES-1), respectively, are key players in inflammation, and pharmacological suppression of these lipid mediators (LM) represents a strategy to intervene with inflammatory disorders. Previous studies revealed that the benzenesulfonamide scaffold displays efficient 5-LO-inhibitory properties. Here, we structurally optimized benzenesulfonamides which led to an N-phenylbenzenesulfonamide derivative (compound 47) with potent inhibitory activities (IC50 = 2.3 and 0.4 μM for isolated 5-LO and 5-LO in intact cells, respectively). Compound 47 prevented the interaction of 5-LO with its activating protein (FLAP) at the nuclear envelope in transfected HEK293 cells as shown by in situ proximity ligation assay. Comprehensive assessment of the LM profile produced by human macrophages revealed the ability of 47 to selectively down-regulate pro-inflammatory LMs (i.e. LTs and PGE2) in M1 but to enhance the formation of pro-resolving LMs (i.e. resolvins and maresins) in M2 macrophages. Moreover, 47 strongly inhibited LT formation and cell infiltration in two in vivo models of acute inflammation (i.e., peritonitis and air pouch sterile inflammation in mice). Together, 47 represents a novel LT biosynthesis inhibitor with an attractive pharmacological profile as anti-inflammatory drug that also promotes the biosynthesis of pro-resolving LM.
CO2-Catalyzed Efficient Dehydrogenation of Amines with Detailed Mechanistic and Kinetic Studies
Riemer, Daniel,Schilling, Waldemar,Goetz, Anne,Zhang, Yu,Gehrke, Sascha,Tkach, Igor,Hollóczki, Oldamur,Das, Shoubhik
, p. 11679 - 11687 (2018/11/23)
CO2-catalyzed dehydrogenation of amines has been achieved under photocatalytic conditions. With this concept, various amines have been selectively dehydrogenated to the corresponding imines in the presence of different functional groups such as nitrile, nitro, ester, halogen, ether, thioether, and carbonyl or carboxylic acid moieties. At the end, the CO2-catalyzed synthesis of pharmaceutical drugs has been achieved. The CO2 radical has been detected by EPR spectroscopy using DMPO, and the mechanism of this reaction is proposed on the basis of DFT calculations and experimental evidence.
Photochemically Promoted Aza-Diels-Alder-Type Reaction: High Catalytic Activity of the Cr(III)/Bipyridine Complex Enhanced by Visible Light Irradiation
Arai, Noriyoshi,Ohkuma, Takeshi
, p. 7628 - 7636 (2017/07/26)
Aza-Diels-Alder-type cycloaddition reactions between a range of N-arylimines and functionalized alkenes were effectively catalyzed by the Cr(III)/bipyridine complex under irradiation of blue light, to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in high yields with excellent diastereoselectivity. Typically, the reaction of benzylideneaniline with 1-vinyl-2-pyrrolidinone proceeded smoothly with a substrate-to-catalyst molar ratio (S/C) of 1000 and completed within 4 h at room temperature (20-25 °C), affording the cycloaddition product in 97% yield.
Synthesis of novel β-amino ketones containing a p-aminobenzoic acid moiety and evaluation of their antidiabetic activities
Tang, Guangxia,Yan, Jufang,Fan, Li,Xu, Jin,Song, Xiaoli,Jiang, Li,Luo, Lingfei,Yang, Dacheng
, p. 490 - 504 (2013/07/11)
The synthesis of two series of β-amino ketones containing a p-aminobenzoic acid moiety (TM-1 and TM-2) using a modified protocol of the Mannich reaction is reported. The molecular structures of a total of tweenty three new target compounds were characterized by 1H NMR, 13C NMR, ESI-MS and HR-MS. Subsequently, their antidiabetic activities were screened in vitro. The α-glucodase inhibition (α-GI) activity of compound 1e reached a remarkable level of 66.50%. The peroxisome proliferator-activated receptor (PPAR) relative activation activities of six compounds are above 80%, and in particular 2i displays an unprecedentedly high PPAR of 130.91%. The structure-activity relationships of the compounds were established. 2i is also subject to further in-depth investigation.
Investigation of the substituent specific cross-interaction effects on 13C NMR of the C=N bridging group in substituted benzylidene anilines
Cao, Chenzhong,Lu, Bingtao,Chen, Guanfan
experimental part, p. 335 - 341 (2011/10/09)
The substituent effect on 13C NMR of the C=N in benzylidene anilines XPhCH=NPhY was investigated, in which the substituents X and Y are in p-position or in m-position of the two aromatic rings. The substituent effects including the inductive effects of X and Y, the conjugative effects of X and Y, and the substituent specific cross-interaction effect were put into one model to quantify the 13C NMR chemical shift δC(C=N) of the C=N in XPhCH=NPhY. A penta-parameter correlation equation with correlation coefficient 0.9975 and standard error 0.17 ppm was obtained for 80 samples of compounds. The result shows that the substituents X and Y have an opposite effect on the δC(C=N). The electron-withdrawing effects of X decrease the δC(C=N); while the electron-donating effects of X increase the δC(C=N). In contrast, the electron-withdrawing effects of Y increase the δC(C=N); while the electron-donating effects of Y decrease the δC(C=N). A new substituent specific cross-interaction effect parameter δσ2 was proposed, which indicates that the most substituent specific cross-interaction effect exists in the pair of max electron-withdrawing group (EWG) and max electron-donating group (EDG) or the pair of max EDG and max EWG. Further to verify the obtained correlation equation, 15 samples of model compounds were prepared and their δC(C=N) was measured in this work. The predicted δC(C=N) values with the obtained equation are in good agreement with the measured ones for these prepared compounds, which confirmed the reliability of the obtained equation.
Synthesis of 4-[(p-alkylanilino-p-alkylphenyl)methyl]-4-butyl-1,2- diphenylpyrazolidine-3,5-diones
Kozlov,Rubis,Tkachev,Basalaeva
, p. 307 - 310 (2008/02/08)
4-Butyl-1,2-diphenylpyrazolidine-3,5-dione derivatives were prepared by its condensation with Schiff bases formed from p-aminobenzoic acid and its methyl and ethyl esters as amine components and substituted aromatic aldehydes. Pleiades Publishing, Inc., 2006.
Nonradical zinc-barbier reaction for diastereoselective synthesis of vicinal amino alcohols
Keinicke, Lise,Fristrup, Peter,Norrby, Per-Ola,Madsen, Robert
, p. 15756 - 15761 (2007/10/03)
A new protocol for the synthesis of vicinal amino alcohols is described. The method employs a Barbier-type reaction between an imine and 3-benzoyloxyallyl bromide in the presence of zinc metal. The addition products are debenzoylated to afford amino alcohols in good yields and with diastereomeric ratios greater than 85:15 in favor of the anti isomer. A Hammett study has been performed which strongly indicates that the allylation does not follow a radical mechanism, but instead an organometallic reagent is formed which subsequently reacts with the imine. A computational study based on this mechanism reproduces the observed diastereoselectivity with high accuracy, but only when a sufficiently large portion of the substrate is included.
SYNTHESIS OF IMINES FROM N-(1-HALOGENOALKYL)HETEROARYLIUM SALTS
Maquestiau, A.,Anders, E.,Eynde, J.-J. Vanden,D'Orazio, P.,Mayence, A.
, p. 523 - 528 (2007/10/02)
A comparison is established for the reactivity of benzaldehyde, N-(1-chlorobenzyl)pyridinium chloride or N-(1-chlorobenzyl)pyrimidinium chloride with several poorly nucleophilic and/or poorly soluble primary amines under mild experimental conditions.
