103-53-7Relevant articles and documents
A rapid and practical catalytic esterification for the preparation of caffeic acid esters
Xie, Dongsheng,Yang, Fengzhi,Xie, Jin,Zhang, Man,Liu, Wenlu,Fu, Lei
, p. 695 - 700 (2014)
A convenient and practical catalytic method for the preparation of caffeic acid esters is reported. This esterification was carried out with high efficiency in the presence of ytterbium triflate in nitromethane without any other auxiliary reagents. The wide scope of application and especially the higher reactivity and more convenient procedure than previous methods make it a valuable application for the synthesis of caffeic acid esters and other cinnamic acid esters.
Photoinduced Oxidative Alkoxycarbonylation of Alkenes with Alkyl Formates
Tang, Wan-Ying,Chen, Ling,Zheng, Ming,Zhan, Le-Wu,Hou, Jing,Li, Bin-Dong
supporting information, p. 3939 - 3943 (2021/05/26)
A photoinduced oxidative alkoxycarbonylation of alkenes initiated by intermolecular addition of alkoxycarbonyl radicals has been demonstrated. Employing alkyl formates as alkoxycarbonyl radical sources, a range of α,β-unsaturated esters were obtained with good regioselectivity and E selectivity under ambient conditions.
Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles
Biswas, Srijit,Biswas, Subrata,Duari, Surajit,Elsharif, Asma M.,Maity, Srabani,Roy, Arnab
supporting information, p. 3569 - 3572 (2021/07/22)
We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.
Synthesis of Diverse Hydroxycinnamoyl Phenylethanoid Esters Using Escherichia coli
Song, Min Kyung,Cho, A Ra,Sim, Geunyoung,Ahn, Joong-Hoon
, p. 2028 - 2035 (2019/02/26)
Caffeic acid phenethyl ester (CAPE) is an ester of a hydroxycinnamic acid (phenylpropanoid) and a phenylethanoid (2-phenylethanol; 2-PE), which has long been used in traditional medicine. Here, we synthesized 54 hydroxycinnamic acid-phenylethanoid esters by feeding 64 combinations of hydroxycinnamic acids and phenylethanols to Escherichia coli harboring the rice genes OsPMT and Os4CL. The same approach was applied for ester synthesis with caffeic acid and eight different phenyl alcohols. Two hydroxycinnamoyl phenethyl esters, p-coumaroyl tyrosol and CAPE, were also synthesized from glucose using engineered E. coli by introducing genes for the synthesis of substrates. Consequently, we synthesized approximately 393.4 mg/L p-coumaroyl tyrosol and 23.8 mg/L CAPE with this approach. Overall, these findings demonstrate that the rice PMT and 4CL proteins can be used for the synthesis of diverse hydroxycinnamoyl phenylethanoid esters owing to their promiscuity and that further exploration of the biological activities of these compounds is warranted.
Caffeic acid phenethyl ester (CAPE)-derivatives act as selective inhibitors of acetylcholinesterase
Gie?el, Josephine M.,Loesche, Anne,Csuk, René
, p. 259 - 268 (2019/06/05)
Unexpected inhibitory effects against eeAChE could be found for a newly synthesized class of caffeic acid phenethyl ester (CAPE)derivatives. Thus, phenethyl-(E)-3-(3,5-dimethoxy-4-phenethoxyphenyl)-acrylate (Ki = 1.97 ± 0.38 μM, Ki′ = 2.44 ± 0.07 μM)and 4-(2-(((E)-3-(3,4-bis(benzyloxy)phenyl)acryloyl)oxy)ethyl)-1,2-phenylene (2E,2′E)-bis(3-(3,4-bis(benzyloxy)phenyl)acrylate)(Ki = 0.72 ± 0.31 μM, Ki′ = 1.80 ± 0.21 μM)showed very good inhibition of eeAChE, while being non cytotoxic for malignant human cancer cells and non-malignant mouse fibroblasts. Also, they are weak inhibitors for BChE (from equine serum).
Synthesis of amide and ester derivatives of cinnamic acid and its analogs: Evaluation of their free radical scavenging and monoamine oxidase and cholinesterase inhibitory activities
Takao, Koichi,Toda, Kazuhiro,Saito, Takayuki,Sugita, Yoshiaki
, p. 1020 - 1027 (2017/11/17)
A series of cinnamic acid derivatives, amides (1–12) and esters (13–22), were synthesized, and structure–activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1–10, 12–18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxy-indole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9–11, 15, 17–22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer’s disease.
Structure–activity relations of rosmarinic acid derivatives for the amyloid β aggregation inhibition and antioxidant properties
Taguchi, Riho,Hatayama, Koki,Takahashi, Tomohito,Hayashi, Takafumi,Sato, Yuki,Sato, Daisuke,Ohta, Kiminori,Nakano, Hiroto,Seki, Chigusa,Endo, Yasuyuki,Tokuraku, Kiyotaka,Uwai, Koji
supporting information, p. 1066 - 1075 (2017/08/02)
Amyloid-β aggregation inhibitors are expected to be therapeutic or prophylactic agents for Alzheimer's disease. Rosmarinic acid, which is one of the main aggregation inhibitors derived from Lamiaceae, was employed as a lead compound and its 25 derivatives were synthesized. In this study, the structure–activity relations of rosmarinic acid derivatives for the amyloid-β aggregation inhibitory effect (MSHTS assay), antioxidant properties, and xanthine oxidase inhibition were evaluated. Among the tested compounds, compounds 16d and 19 were found to the most potent amyloid aggregation inhibitors. The SAR revealed that the necessity of the presence of the phenolic hydroxyl on one side of the molecule as well as the lipophilicity of the entire molecule. The importance of these structural properties was also supported by docking simulations.
A highly efficient Pd/CuI-catalyzed oxidative alkoxycarbonylation of α-olefins to unsaturated esters
Maffei, Mathias,Giacoia, Gabriele,Mancuso, Raffaella,Gabriele, Bartolo,Motti, Elena,Costa, Mirco,Della Ca’, Nicola
, p. 435 - 443 (2016/12/16)
A new protocol for the alkoxycarbonylation of α-olefins to the corresponding unsaturated esters has been developed. Differently substituted styrenes were selectively converted to cinnamate derivatives, via C[sbnd]H bond functionalization. Various palladium sources, including heterogeneous ones, in combination with CuI exhibited a high catalytic efficiency using oxygen as the most cheap oxidant. Monocarbonylated products were obtained in good yields and high chemoselectivity working with a low CO pressure (2 atm) and an excess of air (35 atm) avoiding in this way explosion risks. Commercial cinnamate derivatives were prepared in good to excellent yields by this very simple one-pot procedure.
Synthesis of caffeic acid phenethyl ester analogues and their cytotoxicities against human cancer cells
Wang, Yan-Hui,Li, Qu-Sheng,Wang, Peng-Long,Xu, Kuo,Cheng, Ya-Tao,Xu, Xin,Li, Qiang,Zhang, Yu-Zhong,Lei, Hai-Min
, p. 2686 - 2690 (2014/06/09)
Although caffeic acid phenethyl ester exhibits strong antitumor property, but its pharmacophore has not been elaborated clearly as yet. Seventeen caffeic acid phenethyl ester analogues were synthesized via simple and easy procedures and their antiprolifer
Synthesis of caffeic acid phenethyl ester derivatives, and their cytoprotective and neuritogenic activities in PC12 cells
Shi, Haiming,Xie, Dongsheng,Yang, Ruoling,Cheng, Yaqian
, p. 5046 - 5053 (2015/04/22)
Twenty-one caffeic acid phenethyl ester (CAPE) derivatives were synthesized, and characterized by IR, HR-MS, 1H and 13C NMR analyses. All compounds were evaluated for their cytoprotective effects against H2O2-induced cytotoxicity and neuritogenic activities in the neurite outgrowth in PC12 cells. Compounds 1 and 20 exhibited stronger cytoprotective activities than their parent compound CAPE at 4 nM. Compounds 1, 4, 12 and 13 showed potential neuritogenic activities at 0.5 nM, while compounds 19 and 20 induced neurite outgrowth at 10 nM. The results from this study suggested that CAPE and its derivatives may be potential functional food ingredients for the prevention of neurodegenerative diseases.
