42265-58-7

Usage

InChI:InChI=1/C11H15NO2/c1-3-12-10-7-5-9(6-8-10)11(13)14-4-2/h5-8,12H,3-4H2,1-2H3

Upstream product

• 75-07-0 acetaldehyde 
• 94-09-7 p-aminoethylbenzoate 
• 5338-44-3 ethyl p-acetamidobenzoate 
• 74-96-4 ethyl bromide 
• 150-13-0 4-amino-benzoic acid 
• 64-17-5 ethanol 
• 99-77-4 ethyl 4-nitrobenzoate 
• 64-67-5 diethyl sulfate 

Downstream Products

• 19164-03-5 4-ethylamino-benzoic acid-(2-hydroxy-3-pyrrolidino-propyl ester) 
• 912947-85-4 4-[(3-chloro-propionyl)-ethyl-amino]-ethyl benzoate 

Relevant academic research and scientific papers

A highly efficient Co-based catalyst fabricated by coordination-assisted impregnation strategy towards tandem catalytic functionalization of nitroarenes with various alcohols

A well-defined hexamethylenetetramine (abbreviated as HMTA) based two-dimensional (2D) MOFs metalloligand (termed Zn-HMTA), with free uncoordinated tertiary amine groups, has been synthesized via solution diffusion method for the first time. The crystal structure of 2D Zn-HMTA metalloligand was determined by the single crystal X-ray diffraction (SCXRD). The SCXRD and X-ray photoelectron spectroscopy (XPS) analyses have revealed that the 2D Zn-HMTA metalloligand is rich in- free tertiary amine groups, which are of strong coordination ability to transition metal ions (e.g. Ni2+, Co2+, Zn2+, Cu2+). As a result, a 2D bimetallic Co@Zn-HMTA MOFs was synthesized via coordination-assisted impregnation (CAI) strategy attributed to the unique feature of strong coordinated ability of free tertiary amine groups. Furthermore, a series of self-supported Co-ZnO-CN nanocatalysts were afforded upon the as-synthesized Co@Zn-HMTA MOFs served as a self-sacrificial template for pyrolysis at different temperatures. The optimized catalyst (termed as Co-ZnO@CN-CAI) demonstrated the excellent catalytic performance for hydrogenation-alkylation tandem reaction in comparison with the classic ZnO@CN composite (derived from Zn-HMTA MOFs) supported metallic Co catalyst (Co-ZnO@CN-IWI) prepared by incipient wetness impregnation method. Moreover, the kinetic study was also performed to confirm that the alkylation is the rate-determining step in the hydrogenation-alkylation tandem reaction. The origin of enhanced catalytic performance of Co-ZnO@CN-CAI and the role of Co@Zn-HMTA MOFs precursor have been explored by way of various characterizations, e.g. HADDF-STEM-EDS, SEM-EDS, 13C MAS NMR, XRD, Raman and XPS, etc. It is anticipated that the prepared low-cost and easily prepared 2D Zn-HMTA metalloligand will become a general template for synthesis of highly self-supported catalysts with coordination-assisted impregnation strategy (CAI) for various catalytic reactions.

Characterization of Conformationally Constrained Benzanilide Scaffolds for Potent and Selective HDAC8 Targeting

Histone deacetylases (HDACs) are an attractive therapeutic target for a variety of human diseases. Currently, all four FDA-approved HDAC-targeting drugs are nonselective, pan-HDAC inhibitors, exhibiting adverse side effects at therapeutic doses. Although selective HDAC inhibition has been proposed to mitigate toxicity, the targeted catalytic domains are highly conserved. Herein, we describe a series of rationally designed, conformationally constrained, benzanilide foldamers which selectively bind the catalytic tunnel of HDAC8. The series includes benzanilides, MMH371, MMH409, and MMH410, which exhibit potent in vitro HDAC8 activity (IC50 = 66, 23, and 66 nM, respectively) and up to 410-fold selectivity for HDAC8 over the next targeted HDAC. Experimental and computational analyses of the benzanilide structure docked with human HDAC8 enzyme showed the adoption of a low-energy L-shaped conformer that favors HDAC8 selectivity. The conformationally constrained HDAC8 inhibitors present an alternative biological probe for further determining the clinical utility and safety of pharmacological knockdown of HDAC8 in diseased cells.

A strategy of two-step tandem catalysis towards direct N-alkylation of nitroarenes with ethanol via facile fabricated novel Co-based catalysts derived from coordination polymers

Three novel N-doped carbon supported Co/Co3O4 catalysts, namely, Co@CN-hmta, Co@CN-larg and Co-Co3O4@CN-bipy, with sheet-, worm-, honeycomb-like morphologies respectively, have been fabricated by the pyrolysis of well-defined coordination polymers (CPs). Upon the as-prepared catalysts were applied for the reaction of N-alkylation of nitroarenes with ethanol, a direct two-step tandem reaction is realized, in which the Co@CN-hmta delivers 100% conversion/selectivity of N-ethylaniline/N,N-diethylaniline from the direct N-alkylation of nitroarenes with ethanol. The kinetic studies were conducted to confirm that the N-alkylation of aniline with ethanol is the rate-determining step in the two-step tandem reaction. The SEM/EDX, XRD, Raman, TEM, XPS, and CO2-TPD characterization results have revealed that sizes and dispersion of metallic Co, amount of structural defects and surface Lewis basicity towards three catalysts can be tuned by changing the structures of Co-based CPs designed by different organic linkers, which may also help to understand the preparation of industrial catalysts on a molecular level. The optimized Co@CN-hmta catalyst is easily recycled by using the external magnet for successive reuses without any loss in both activity and selectivity. To the best of our knowledge, this is the first carbon-nitrogen species supported Co/Co3O4 catalysts derived from the CPs, which could effectively catalyzed the N-alkylation of nitroarenes with ethanol to produce the secondary amines and/or tertiary amines. This low-cost, recyclable and easy scale-up N-doped carbon supported catalyst may be of potential application in various heterogeneous catalytic reactions.

O -Phenylenediamine: A privileged pharmacophore of ferrostatins for radical-trapping reactivity in blocking ferroptosis

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.

Versatile, mild, and selective reduction of various carbonyl groups using an electron-deficient boron catalyst

A mild and selective new method was discovered to reduce acetanilides and other carbonyl compounds. Unlike sodium borohydride, which is selective in reducing aldehydes and ketones, this new protocol is uniquely selective in reducing acetanilides and nitriles over other carbonyl containing functional groups. Additionally, β-ketoamides were shown to be reduced at the ketone preferentially over the amide.

Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines

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.

NPY ANTAGONISTS, PREPARATION AND USES

The present invention concerns novel compounds, their preparation and their uses, therapeutic uses in particular. More specifically it concerns derivative compounds having at least two aromatic cycles, their preparation and their uses, in particular in the area of human or animal health. These compounds have an affinity for the biological receptors of neuropeptide Y, NPY, present in the central and peripheral nervous systems. The compounds of the invention are preferably NPY antagonists, and more particularly antagonists of sub-type NPY Y1, and can therefore be used for the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also concerns pharmaceutical compositions containing said compounds, their preparation and their uses, as well as treatment methods using said compounds.

An Efficient Reduction Of Nitriles And Amides To The Corresponding Amines With Tetra-N-Butylammonium Borohydride In Dichloromethane

The reduction of nitriles and amides to the corresponding amines with tetra-n-butylammonium borohydride in dichloromethane has been reported, in which the other functional groups such as ester, nitro, and halogen attached to the aromatic ring are not affected.