15298-28-9

Usage

Uses

Used in Pharmaceutical Research and Development:
N-(2-hydroxy-2-(4-Methoxyphenyl)ethyl)benaMide is utilized as a key component in the research and development of new drugs. Its unique chemical structure and properties contribute to the creation of innovative pharmaceutical formulations.
Used in Organic Synthesis:
In the field of organic synthesis, N-(2-hydroxy-2-(4-Methoxyphenyl)ethyl)benaMide is employed as an intermediate. This role allows for its incorporation into a wide range of chemical reactions and processes, enhancing the synthesis of various organic compounds.
Used in Chemical Reactions and Processes:
N-(2-hydroxy-2-(4-Methoxyphenyl)ethyl)benaMide is also used in various chemical reactions and processes due to its versatility and valuable properties, making it an essential component in the production of a diverse array of organic compounds.

InChI:InChI=1/C16H17NO3/c1-20-14-9-7-12(8-10-14)15(18)11-17-16(19)13-5-3-2-4-6-13/h2-10,15,18H,11H2,1H3,(H,17,19)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 6595-28-4 2-azido-1-(4-methoxyphenyl)ethan-1-one 
• 144924-01-6 β-azido-α-(4-methoxyphenyl)ethanol 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 637-69-4 4-Methoxystyrene 
• 66985-48-6 2-(4-methoxyphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 55275-61-1 2-amino-1-(4-methoxyphenyl)ethanol 
• 65-85-0 benzoic acid 
• 56766-24-6 2-hydroxy-2-(4-methoxyphenyl)ethylammonium chloride 
• 98-88-4 benzoyl chloride 

Downstream Products

• 15298-31-4 1-acetoxy-2-benzoylamino-1-(4-methoxy-phenyl)-ethane 
• 50802-66-9 tembamide 

Relevant academic research and scientific papers

Nitration-Peroxidation of Alkenes: A Selective Approach to β-Peroxyl Nitroalkanes

Nitration-peroxidation of alkenes for the synthesis of β-peroxyl nitroalkanes has been developed by using tert-butyl nitrite and tert-butyl hydroperoxide. The method presents a new and selective difunctionalization of alkenes to introduce a nitro group and a peroxyl group across the double bonds of alkenes under mild conditions. A radical reaction pathway is proposed by experimental and theoretical studies.

Enantioselective Aminohydroxylation of Styrenyl Olefins Catalyzed by an Engineered Hemoprotein

Chiral 1,2-amino alcohols are widely represented in biologically active compounds from neurotransmitters to antivirals. While many synthetic methods have been developed for accessing amino alcohols, the direct aminohydroxylation of alkenes to unprotected, enantioenriched amino alcohols remains a challenge. Using directed evolution, we have engineered a hemoprotein biocatalyst based on a thermostable cytochrome c that directly transforms alkenes to amino alcohols with high enantioselectivity (up to 2500 TTN and 90 % ee) under anaerobic conditions with O-pivaloylhydroxylamine as an aminating reagent. The reaction is proposed to proceed via a reactive iron-nitrogen species generated in the enzyme active site, enabling tuning of the catalyst's activity and selectivity by protein engineering.

In silico prioritization, synthesis and in vitro evaluation of tembamide analogs for anti-HIV activity

Background: High attrition rate in late drug discovery and development stages leads to financial loss to industries and Governments. Despite the global prevalence of HIV infection and lack of promising treatment for AIDS patients, there are only a few drugs approved for the management of infected patients. There is an urgent need to discover newer anti-HIV drugs with novel mechanism of action and with efforts to reduce attrition rate in early drug discovery stages. Objective: Prioritization of reported potential anti-HIV-1 leads according to their quantitative estimation of druglikeness (QED), carcinogenicity, mutagenicity, absorption, metabolism and toxic properties. Synthesis of analogs of the best lead and evaluation of their anti-HIV-1 activity is shown. Methods: In silico anti-HIV lead prioritization was performed on a set of known anti-HIV natural products in order to obtain a lead with better druglikeness and ADMET properties. Prioritized lead tembamide and its four analogs were synthesized and their anti-HIV-1 activity was evaluated. Results: Tembamide was found to be a lead with better QED, absorption and metabolism properties and with no carcinogenicity, mutagenicity and toxic potential. (+)-Tembamide is previously reported to show potent anti-HIV-1 activity against laboratory adapted strains HIV-1IIIB (X4, subtype B) and HIV-1Ada5 (R5, subtype B) in H9 cell line. It was observed during this study that synthesized tembamide and its four analogs were weakly active against primary isolates HIV-1UG070 (X4, subtype D) and HIV-1VB59 (R5, subtype C) in TZM-bl cell line. Conclusion: The results showed that there is scope for the improvement of activity of tembamide analogs to discover a potent anti-HIV compound.

Chiral metal?Organic framework as a platform for cooperative catalysis in asymmetric cyanosilylation of aldehydes

In this work, we demonstrate cooperative asymmetric catalysis by a metal?organic framework (MOF) as exemplified in the context of catalyzing cyanation of aldehydes with a VO(salen)-MOF, which after oxidation affords remarkably increased stereoselectivity (up to >99% ee) compared to the homogeneous VO(salen) counterpart as a result of the pairs of VO(salen) units in close proximity within its open channels. The cooperative asymmetric catalysis has been evidenced by the significantly decreased stereoselectivity and activity when one VO(salen) in such pairs of VO(salen) units is replaced with one Cu(salen), which results in blocking the VO?VO synergistic pathway while prompting unimolecular activation of substrates. The heterogeneous nature of VO(salen)-MOF has been verified by the fact that it can be easily recycled and reused without significant loss of catalytic activity and enantioselectivity, and its practical utility as asymmetric cyanation catalysist has been illustrated in the gram-scale synthesis of the antiviral natural products (R)- and (S)-enantiomers of tembamide. Our work therefore advances chiral MOF as an attractive platform for cooperative asymmetric catalysis in a variety of syntheses.

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

SYNTHESES OF NATURAL HYDROXYAMIDES USING TRIMETHYLSILYL CYANIDE

New syntheses of tembamide (1), aegeline (2), and other hydroxyamides, using trimethylsilyl cyanide, are described.

Carbon-13 NMR Spectra of Tembamide, Aegeline and Related Amides

Carbon-13 NMR spectral studies of tembamide (1) and aegeline (2), constituents of Fagara hyemalis and Aegle marmelos respectively, and a series of their structurally related amides (3-13) have been carried out.The assignment of the resonances of two related dimers are also reported.The assignment of the various resonances were made by considering the changes in chemical shifts produced by the change of substituents and also by using 1, 13 and a related compound as model compounds.