857035-61-1

Usage

Structure

Ethanolamine derivative with a substituted phenylamino group

Usage

Building block for the synthesis of various pharmaceuticals and other organic compounds in organic synthesis and pharmaceutical research

Physical state

Colorless liquid at room temperature

Molecular weight

179.26 g/mol

General use

Intermediate in the production of various fine chemicals and pharmaceutical compounds

Specific properties and uses

Exact properties and uses may vary depending on the specific application

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 107-07-3 2-chloro-ethanol 
• 107-21-1 ethylene glycol 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 141-43-5 ethanolamine 
• 540-51-2 2-bromoethanol 

Downstream Products

• 1335044-87-5 C₄₂H₆₀N₆O₉ 
• 1606589-16-5 C₁₉H₃₁NO₂Si 
• 1606589-27-8 C₁₃H₁₇NO₂ 
• 1606589-51-8 1-(3,5-dimethylphenyl)-4-hydroxy-3-methylenepyrrolidin-2-one 
• 1606589-39-2 C₁₃H₁₅NO₂ 

Relevant academic research and scientific papers

β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction

Borrowing Hydrogen (BH), also called Hydrogen Autotransfer (HA), reaction with neat ethylene glycol represents a key step in the preparation of β-amino alcohols. However, due to the stability of ethylene glycol, mono-activation has rarely been achieved. Herein, a combination of Pd/C and ZnO is reported as heterogeneous catalyst for this BH/HA reaction. This system results in an extremely air and moisture stable, and economic catalyst able to mono-functionalize ethylene glycol in water, without further activation of the diol. In this work, different diols and aromatic amines have been explored affording a new approach towards amino alcohols. This study reveals how the combination of two solid species can afford interesting catalytic properties in heterogeneous phase. ZnO activates ethylene glycol while Pd/C is the responsible of the BH/HA cycle. This catalytic system has also been found useful to dehydrogenate indoles affording indolines that undergo in situ BH/HA cycle prior to re-aromatization, representing a tandem heterogeneous process.

N-Arylazetidines: Preparation through Anionic Ring Closure

We report herein an efficient synthesis of diversely substituted N-aryl-2-cyanoazetidines based on an anionic ring-closure reaction. These compounds can be prepared from β-amino alcohols in enantiomerically pure form through a three-step sequence involving (i) copper-catalyzed N-arylation, (ii) N-cyanomethylation of the secondary aniline, and (iii) one-pot mesylation followed by ring closure induced by a base. This high-yielding sequence gives access to azetidines with a predictable and adjustable substitution pattern and also with predictable diastereoselectivity. These compounds are susceptible to multiple further derivatizations through Suzuki coupling or nitrile transformation, thus appearing as valuable new scaffolds for medicinal chemistry. Their rigid shape, featuring an almost planar N-arylamine and a planar four-membered ring, was revealed by both AM1 calculations and X-ray crystallography.

Searching for New Leads for Tuberculosis: Design, Synthesis, and Biological Evaluation of Novel 2-Quinolin-4-yloxyacetamides

In this study, a new series of more than 60 quinoline derivatives has been synthesized and evaluated against Mycobacterium tuberculosis (H37Rv). Apart from the SAR exploration around the initial hits, the optimization process focused on the improvement of the physicochemical properties, cytotoxicity, and metabolic stability of the series. The best compounds obtained exhibited MIC values in the low micromolar range, excellent intracellular antimycobacterial activity, and an improved physicochemical profile without cytotoxic effects. Further investigation revealed that the amide bond was the source for the poor blood stability observed, while some of the compounds exhibited hERG affinity. Compound 83 which contains a benzoxazole ring instead of the amide group was found to be a good alternative, with good blood stability and no hERG affinity, providing new opportunities for the series. Overall, the obtained results suggest that further optimization of solubility and microsomal stability of the series could provide a strong lead for a new anti-TB drug development program.

Photoinduced self-structured surface pattern on a molecular azo glass film: Structure-property relationship and wavelength correlation

In this study, three series of star-shaped molecular azo glasses were synthesized, and self-structured surface pattern formation on the azo compound films was studied by laser irradiation at different wavelengths. The molecular azo glasses were synthesized from three core precursors (Tr-AN, Tr-35AN, Tr-H35AN), which were prepared by ring-opening reactions between 1,3,5-triglycidyl isocyanurate and corresponding aniline derivatives. The star-shaped azo compounds were obtained through azo-coupling reactions between the core precursors and diazonium salts of 4-chloroaniline, 4-aminobenzonitrile, and 4-nitroaniline, respectively. By using the two-step reaction scheme, three series of azo compounds with different structures were obtained. The core precursors and azo compounds were characterized by using 1H NMR, FT-IR, UV-vis, mass spectrometry, and thermal analyses. The self-structured surface pattern formation on films of the azo compounds was studied by irradiating the azo compound films with a normal-incident laser beam at different wavelengths (488, 532, and 589 nm). The results show that the photoinduced surface pattern formation behavior is closely related to the structure of the azo compounds, excitation wavelength, and light polarization conditions. The absorption band position of the π-π* transition is mainly determined by the electron-withdrawing groups on the azo chromophores. When the excitation wavelength is between λmax and the band tail at the longer wavelength side, the self-structured surface patterns can be more efficiently induced to form on the films. The 3,5-dimethyl substitution on azo chromophores inhibits the surface pattern formation for certain excitation wavelengths. Increasing molecular interaction also shows an effect of restraining the surface pattern formation. The irradiations with linearly and circularly polarized light cause significant differences in the alignment manner of the pillarlike structures and their saturated height.

Selection of a respiratory syncytial virus fusion inhibitor clinical candidate. 2. Discovery of a morpholinopropylaminobenzimidazole derivative (TMC353121)

A preceding paper (Bonfanti et al. J. Med Chem. 2007, 50, 4572-4584) reported the optimization of the pharmacokinetic profile of substituted benzimidazoles by reducing their tissue retention. However, the modifications that were necessary to achieve this goal also led to a significant drop in anti-RSV activity. This paper describes a molecular modeling study followed by a lead optimization program that led to the recovery of the initial potent antiviral activity and the selection of TMC353121 as a clinical candidate.

MORPHOLINYL CONTAINING BENZIMIDAZOLES AS INHIBITORS OF RESPIRATORY SYNCYTIAL VIRUS REPLICATION

The present invention concerns morpholinyl containing benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula (I), a prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereoc