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.
Straightforward access to high-performance organometallic catalysts by fluoride activation: Proof of principle on asymmetric cyanation, asymmetric Michael addition, CO2 addition to epoxide, and reductive alkylation of amines by tetrahydrofuran
Chusov, Denis,Tsygankov, Alexey A.
, p. 13077 - 13084 (2021/11/01)
We demonstrate that well-known transition metal catalysts can be transformed into high-performance versions by the simple use of a fluoride anion source. In situ fluoride-activated catalysts are highly active catalytic species. The isolation may lead to degradation of the species or a decrease in catalytic activity. Fluoride activation of known, relatively simple catalysts resulted in the development of one of the most efficient catalytic systems for the asymmetric cyanation of aldehydes, asymmetric Michael addition, and synthesis of cyclic carbonates. Furthermore, the fluoride-assisted reductive opening of tetrahydrofuran (THF) with amines was developed. We believe that the proposed approach can find broad applications in the enhancement of known catalytic processes and in the design of new ones.
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.
O -Phenylenediamine: A privileged pharmacophore of ferrostatins for radical-trapping reactivity in blocking ferroptosis
Sheng, Xie-Huang,Cui, Cheng-Cheng,Shan, Chao,Li, Yu-Zhen,Sheng, Duo-Hong,Sun, Bin,Chen, De-Zhan
, p. 3952 - 3960 (2018/06/11)
Ferroptosis is a non-apoptotic, iron dependent form of regulated cell death that is characterized by the accumulation of lipid hydroperoxides. It has drawn considerable attention owing to its putative involvement in diverse neurodegenerative diseases. Ferrostatins are the first identified inhibitors of ferroptosis and they inhibit ferroptosis by efficiently scavenging free radicals in lipid bilayers. However, their further medicinal application has been limited due to the deficient knowledge of the lipid peroxyl radical-trapping mechanism. In this study, experimental and theoretical methods were performed to illustrate the possible lipid hydroperoxide inhibition mechanism of ferrostatins. The results show that an ortho-amine (-NH) moiety from ferrostatins can simultaneously interact with lipid radicals, and then form a planar seven-membered ring in the transition state, and finally present greater reactivity. NBO analysis shows that the formed planar seven-membered ring forces ortho-amines into better alignment with the aromatic π-system. It significantly increases the magnitudes of amine conjugation and improves spin delocalization in the transition state. Additionally, a classical H-bond type interaction was discovered between a radical and an o-NH group as another transition state stabilizing effect. This type of radical-trapping mechanism is novel and has not been found in diphenylamine or traditional polyphenol antioxidants. It can be said that o-phenylenediamine is a privileged pharmacophore for the design and development of ferroptosis inhibitors.
Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
Yuan, Ming-Lei,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 3036 - 3040 (2016/10/11)
The hydrogenation of amides to amines has been developed by using the catalyst [Ru(H)2(CO)(Triphos)] (Triphos=1,1,1-tri(diphenylphosphinomethyl)ethane) and catalytic boron Lewis acids such as B(C6F5)3 or BF3?Et2O as additives. The reaction provides an efficient method for the preparation of secondary amines from amides in good yields with high selectivity.
Reductive N -alkylation of nitroarenes: A green approach for the N-alkylation of natural products
Wahba, Amir E.,Hamann, Mark T.
experimental part, p. 4578 - 4585 (2012/06/30)
A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.
One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes
Byun, Eunyoung,Hong, Bomi,De Castro, Kathlia A.,Lim, Minkyung,Rhee, Hakjune
, p. 9815 - 9817 (2008/03/27)
(Chemical Equation Presented) One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using various aldehydes by Pd/C catalyst in aqueous 2-propanol solvent with ammonium formate as in situ hydrogen donor is illustrated. The reaction proceeded smoothly and selectively with excellent yield at room temperature. Our protocol presents a facile, economical, and environmentally benign alternative for reductive amination.
SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
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, (2008/06/13)
The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
