70185-64-7

Basic information

• Product Name: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-
• CAS NO: 70185-64-7
• Molecular Formula: C₁₇H₁₇NO₄
• Molecular Weight: 299.3212
• Mol File: 70185-64-7.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-(70185-64-7)
• EPA Substance Registry System: 2-Propenamide, 3-(3,4-dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]-(70185-64-7)

Safety Data

• Hazardous Substances Data: 70185-64-7(Hazardous Substances Data)

Usage

Main properties

1. Chemical compound
2. Potential biological and pharmaceutical applications

Specific content

Molecular structure includes a propenamide group, hydroxyphenyl group, and ethyl group
Contains phenolic and amide functional groups
Potential antioxidant and antimicrobial properties
Potential therapeutic effects
Multiple aromatic rings suggest notable chemical reactivity
Potential interactions with other biological compounds
Further research needed to elucidate pharmacological and biochemical properties

Upstream product

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Downstream Products

• 1596210-12-6 6,9,10-trihydroxy-N,N-bis(4-hydroxyphenethyl)benzo[k,l]xanthene-1,2-dicarboxamide 

Relevant articles and documents

Identification and quantification of potential anti-inflammatory hydroxycinnamic acid amides from wolfberry

Wolfberry or Goji berry, the fruit of Lycium barbarum, exhibits health-promoting properties that leads to an extensive study of their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized LC-MS/MS and NMR analysis, nine amide compounds were identified from the fruits. Seven of these compounds were identified in this plant for the first time. The amide compounds with a tyramine moiety were the most abundant. In vitro studies indicated that five HCCA compounds showed inhibitory effect on NO production inuded by lipopolysaccharides with IC50 less than 15.08 μM (trans-N-feruloyl dopamine). These findings suggested that wolfberries demonstrated anti-inflammatory properties.

Dihydrobenzofuran Neolignanamides: Laccase-Mediated Biomimetic Synthesis and Antiproliferative Activity

The biomimetic synthesis of a small library of dihydrobenzofuran neolignanamides (the natural trans-grossamide (4) and the related compounds 21-28) has been carried out through an eco-friendly oxidative coupling reaction mediated by Trametes versicolor laccase. These products, after complete spectroscopic characterization, were evaluated for their antiproliferative activity against Caco-2 (colon carcinoma), MCF-7 (mammary adenocarcinoma), and PC-3 (prostate cancer) human cells, using an MTT bioassay. The racemic neolignamides (±)-21 and (±)-27, in being the most lipophilic in the series, were potently active, with GI50 values comparable to or even lower than that of the positive control 5-FU. The racemates were resolved through chiral HPLC, and the pure enantiomers were subjected to ECD measurements to establish their absolute configurations at C-2 and C-3. All enantiomers showed potent antiproliferative activity, with, in particular, a GI50 value of 1.1 μM obtained for (2R,3R)-21. The effect of (±)-21 on the Caco-2 cell cycle was evaluated by flow cytometry, and it was demonstrated that (±)-21 exerts its antiproliferative activity by inducing cell cycle arrest and apoptosis.

Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides

Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.