94-32-6Relevant articles and documents
Folded-to-unfolded structural switching of a macrocyclic aromatic hexaamide based on conformation changes in the amide groups induced by N-alkylation and dealkylation reactions
Katagiri, Kosuke,Tohaya, Taichi,Shirai, Riwako,Kato, Takako,Masu, Hyuma,Tominaga, Masahide,Azumaya, Isao
, p. 23 - 28 (2014)
A macrocyclic compound has been designed and synthesized containing six para-phenylene groups and six alternate N-butyl and N-4-methoxybenzyl substituted amides. The three N-4-methoxybenzyl groups could be removed by N-dealkylation under acidic conditions to give the corresponding secondary amides, which underwent a switch in their conformation from cis to trans. Single crystal X-ray crystallographic analysis revealed that the macrocyclic compound containing six alternate N-butyl and N-4-methoxybenzyl substituted tertiary amide groups existed as the "folded" structure, whereas the macrocyclic compound with six alternate tertiary and secondary amide groups existed as the "unfolded" structure. Furthermore, these changes in the conformation of the hexaamide displayed reversible switching between the "folded" and "unfolded" states.
Production method of chemical product ethyl4-(butylamino)benzoate
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Paragraph 0006, (2019/10/02)
The invention relates to a production method of a chemical product ethyl4-(butylamino)benzoate, which is characterized in that ethyl p-aminobenzoate and n-butyraldehyde are selected as raw materials,palladium, platinum and other catalysts with high activity are selected, and hydrogen is used as reducing agent to synthesize target product in one step. The method has the advantages of simple production mode, friendly environment protection, high yield and low cost, and meets the requirements of large-scale production.
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.
