77201-71-9

Upstream product

• 331-39-5 caffeic acid 

Downstream Products

• 100042-34-0 (E)-3-(3,4-dihydroxyphenyl)-1-morpholinoprop-2-en-1-one 
• 53755-02-5 3-(3,4-dihydroxy-phenyl)-2-[3-(3,4-dihydroxy-phenyl)-acryloylamino]propionic acid 
• 161364-58-5 (E)-3-(3,4-Dihydroxy-phenyl)-1-[2-(2-methoxy-phenoxymethyl)-thiazolidin-3-yl]-propenone 
• 83504-42-1 n-propyl caffeate 
• 104594-70-9 Caffeic acid phenethyl ester 
• 115610-32-7 (2E)-cinnamyl 3-(3,4-dihydroxyphenyl)acrylate 
• 130734-47-3 (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid benzyl ester 
• 22020-28-6 n-butyl caffeate 

Relevant academic research and scientific papers

Cardioprotection of CAPE-oNO2 against myocardial ischemia/reperfusion induced ROS generation via regulating the SIRT1/eNOS/NF-κB pathway in vivo and in vitro

Caffeic acid phenethyl ester (CAPE) could ameliorate myocardial ischemia/reperfusion injury (MIRI) by various mechanisms, but there hadn't been any reports on that CAPE could regulate silent information regulator 1 (SIRT1) and endothelial nitric oxide syn

CAFFEIC ACID DERIVATIVES AND USES THEREOF

The present invention relates to compounds of formula (I): including any stereochemically isomeric form thereof, or pharmaceutically acceptable salts thereof, for the treatment of tuberculosis.

Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors

Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 μM and 8.5 μM against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with Ki = 11.5 ± 0.25 μM by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus.

Discovery of a series of novel compounds with moderate anti-avian H5N1 influenza virus activity in chick embryo

Enlightened by some flavonoid compounds, which had been found as influenza neuraminidase inhibitors, we designed and synthesized a series of novel compounds containing different amino acid fragments. We also reported a simple synthetic route from oseltamivir to prepare its active form which was used as the positive control. The result of enzyme inhibition assay indicated that all the designed compounds displayed weak inhibitory activity against neuraminidase. However, they showed moderate anti-avian H5N1 influenza virus activity in chick embryo. Besides interfering with the function of neuraminidase, these compounds seemed to inhibit the replication of influenza virus by some other mechanism which deserved deep study.

Inhibitory effects of substituted cinnamic acid esters on mushroom tyrosinase

A series of substituted cinnamic acid esters were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. Compound 8 was found to be the most potent inhibitor with IC 50 value of 5.60μM. Preliminary structure activity relationships (SARs) were concluded. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 8 was anti-competitive inhibitor.

Derivatives of Propane Diyl Dicinnamate

The present invention provides a method for treating a cancer in a subject involving administering to the subject a compound of formula (II) or (II′): wherein R1, R2, R3, R4, R5, R6 and Rs

ANTI CANCER USE OF CAFFEIC ACID AND DERIVATIVES

The present invention relates to the use of caffeic acid or a derivative thereof represented by the following general formula (1 ) wherein X is O, NH, or heterocyclyl; R may be present or absent and if present, is H, alkyl, aryl, or heterocyclyl; in all its stereoisomeric and tautomeric forms, and mixtures thereof in all ratios, and a pharmaceutically acceptable salt, pharmaceutically acceptable solvate, pharmaceutically acceptable polymorph or a prodrug, in the treatment of chronic myeloid leukemia (CML) which is resistant to treatment with Gleevec. The invention also relates to a method for reducing the proliferation of cells that are resistant to Gleevec by contacting the cells with a compound of general formula (1 ). The present invention also relates to pharmaceutical compositions (for the manufacture of the medicament) including caffeic acid or a derivative or a salt thereof represented by the general formula (1 ) for the treatment of chronic myeloid leukemia (CML) that is resistant to treatment with Gleevec, or for reducing the proliferation of cells that are resistant to Gleevec. The present invention further relates to a method of treatment of chronic myeloid leukemia (CML) that is resistant to treatment with Gleevec.

Impact of alkyl esters of caffeic and ferulic acids on tumor cell proliferation, cyclooxygenase enzyme, and lipid peroxidation

The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C12-caffeate), 11 (C16-caffeate), 21 (C 8-ferulate), and 23 (C12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 μg/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 μg/ mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 μg/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 μg/ mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C4-C 12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C3-C8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 μg/mL. Long-chain caffeates 11-14 (C 16-C22) and short-chain ferulates 15-20 (C 3-C5) were the most active in lipid peroxidation inhibition and showed 60-70% activity at 5 μg/mL concentration.

Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line

Caffeic acid phenethyl ester (CAPE, 2) and its 20 analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02μM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10μg/mL towards murine colon 26-L5 carcinoma cells. Copyright

A one pot process for the preparation of caffeic acid ester derivatives

The present invention relates to a one pot process for the preparation of caffeic acid ester derivatives of the formula I: ???whereinAr is aryl, which is unsubstituted or substituted with halogen, hydroxy, C1-6 alkyl or C1-6 alkoxy,A is C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene,m is a number from 0 to 6; andB is C1-6 alkyl or aryl, which is unsubstituted or substituted with halogen, hydroxy, C1-6 alkyl or C1-6 alkoxy; ???which process comprises reacting, in a suitable solvent for esterification of a carboxylic acid derivative, a compound of the formula II: ???whereinAr and A are as defined above. ???with a halogenating reagent and alcohol of the formula III:H-(CH2)m-B ???whereinm and B are as defined above.