1220-05-9

Upstream product

• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 56-40-6 glycine 
• 42381-62-4 ethyl (E)-2-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)acetate 
• 50906-12-2 4-acetoxy-3-methoxycinnamoyl chloride 
• 2596-47-6 (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid 

Relevant academic research and scientific papers

Absorption of hydroxycinnamates in humans after high-bran cereal consumption

Hydroxycinnamic acids are a group of phenolic compounds that exhibit a wide range of in vitro chemoprotective and antioxidant properties. Cereals containing a high proportion of the bran layers are rich in ester-linked hydroxycinnamic acids, such as ferul

Synthesis of novel feruloyl dipeptides with proapoptotic potential against different cancer cell lines

In this study, a series of novel N-feruloyl dipeptides (10–17) have been synthesized through the coupling of N-feruloyl amino acids (6–9) with glycine/alanine methyl ester hydrochloride. Structures of the peptides were assigned using 1D and 2D NMR and HRESIMS. According to initial in vitro cytotoxic screening against the cervix carcinoma cell line KB-3-1, aromatic dipeptides (12, 13, 16, 17) were the most potent ones among all tested feruloyl dipeptides. Accordingly, these peptides were further intensively investigated as potential anticancer agents against a panel of ten cancer cell lines from different tissue origin. Based on that, compound 17 showed the strongest cytotoxic efficiency towards the whole panel of tested cell lines with IC50 values from 2.1 to 7.9 μM. By contrast, the dipeptides 12, 13 and 16 showed moderate to weak cytotoxicity (IC50 16.1–28.3 or >30, 5.7–21.9 and 3.9–21.2 or ≥30 μM, respectively). Mechanistically, compound 17 induced a strong dissipation of the mitochondrial transmembrane potential and an early activation of caspase 3/7 in the triple-negative MDA-MB-231 breast cancer cell line. In an in vivo model, compound 17 inhibited growth, proliferation and induced apoptosis in MDA-MB-231 xenografted onto the chick chorioallantoic membrane. All the synthesized compounds were also tested against a set of pathogenic bacterial strains, displaying no potential activity.

Synthesis and characterization of poly[(ferulic acid)-alt-(glycine)]

We investigated the copolymerization of the biomass-derived monomers ferulic acid (FA) and glycine (Gly) to develop a highly thermostable aromatic-aliphatic poly(ester-amide). N-feruloylglycine methyl ester (FAMG), N-feruloylglycine (FAG), and N-(4-O-acet

Structural Fine-Tuning of Desmuramylpeptide NOD2 Agonists Defines Their in Vivo Adjuvant Activity

We report on the design, synthesis, and biological evaluation of a series of nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) desmuramylpeptide agonists with improved in vitro and in vivo adjuvant properties. We identified two promising compounds: 68, a potent nanomolar in vitro NOD2 agonist, and the more lipophilic 75, which shows superior adjuvant activity in vivo. Both compounds had immunostimulatory effects on peripheral blood mononuclear cells at the protein and transcriptional levels, and augmented dendritic-cell-mediated activation of T cells, while 75 additionally enhanced the cytotoxic activity of peripheral blood mononuclear cells against malignant cells. The C18 lipophilic tail of 75 is identified as a pivotal structural element that confers in vivo adjuvant activity in conjunction with a liposomal delivery system. Accordingly, liposome-encapsulated 75 showed promising adjuvant activity in mice, surpassing that of muramyl dipeptide, while achieving a more balanced Th1/Th2 immune response, thus highlighting its potential as a vaccine adjuvant.

Discovery of nanomolar desmuramylpeptide agonists of the innate immune receptor nucleotide-binding oligomerization domain-containing protein 2 (NOD2) possessing immunostimulatory properties

Muramyl dipeptide (MDP), a fragment of bacterial peptidoglycan, has long been known as the smallest fragment possessing adjuvant activity, on the basis of its agonistic action on the nucleotide-binding oligomerization domain-containing protein 2 (NOD2). There is a pressing need for novel adjuvants, and NOD2 agonists provide an untapped source of potential candidates. Here, we report the design, synthesis, and characterization of a series of novel acyl tripeptides. A pivotal structural element for molecular recognition by NOD2 has been identified, culminating in the discovery of compound 9, the most potent desmuramylpeptide NOD2 agonist to date. Compound 9 augmented pro-inflammatory cytokine release from human peripheral blood mononuclear cells in synergy with lipopolysaccharide. Furthermore, it was able to induce ovalbumin-specific IgG titers in a mouse model of adjuvancy. These findings provide deeper insights into the structural requirements of desmuramylpeptides for NOD2-activation and highlight the potential use of NOD2 agonists as adjuvants for vaccines.

α-Glucosidase inhibitory activities of phenolic acid amides with l-amino acid moiety

α-Glucosidase inhibitors can effectively control postprandial hyperglycemia. In this study, a series of phenolic acids with the l-amino acid moiety were synthesized and their inhibitory activities against α-glucosidase from Saccharomyces cerevisiae (EC 3.

Feruloylbenzotriazole and weinreb amide as bioinspired building blocks: A reactivity study towards O-, N-, S-, and C-nucleophiles

A versatile route for the conversion of ferulic acid into biologically relevant molecules is presented. The compatibility of a number of protection and activation strategies with the 1,2-addition of a variety of O-, N-, S-, and C-nucleophiles to ferulic acid is evaluated. In particular, this report contains the first systematic study of the addition of (hetero)aryllithium reagents to 3-phenylpropenoyl Weinreb amides. The relevance of this "bioinspired" method is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, curcuminoids, and (heteroaryl) chalcones. Feruloylbenzotriazole and Weinreb amide were converted into an array of biologically relevant molecules by addition of O-, N-, S-, and C-nucleophiles. The relevance of this bioinspired approach is illustrated by the synthesis of a number of natural products or analogues, such as zingerone, (heteroaryl) chalcones, and curcuminoids. Copyright