246872-15-1Relevant academic research and scientific papers
Synthesis of New Tyrosol-Based Phosphodiester Derivatives: Effect on Amyloid β Aggregation and Metal Chelation Ability
Romanucci, Valeria,Giordano, Maddalena,De Tommaso, Gaetano,Iuliano, Mauro,Bernini, Roberta,Clemente, Mariangela,Garcia-Vi?uales, Sara,Milardi, Danilo,Zarrelli, Armando,Di Fabio, Giovanni
, p. 1172 - 1183 (2021)
Alzheimer's disease (AD) is a multifactorial pathology that requires multifaceted agents able to address its peculiar nature. Increasing evidence has shown that aggregation of amyloid β (Aβ) and oxidative stress are strictly interconnected, and their modu
USE OF PHENOLIC COMPOUNDS FROM OLEA EUROPAEA
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Page/Page column 49-50, (2019/02/25)
A series of phenolic compounds with similar inhibitory COX-1 and COX-2 properties as oleocanthal and oleuropein is described here. The phenolic compounds disclosed here were also found to be MAO and LSD-1 inhibitors. Also provided are methods of using these phenolic compounds in various formulations and compositions including food additives, pharmaceuticals, cosmetics, and animal repellants.
NHC catalyzed enantioselective Coates-Claisen rearrangement: A rapid access to the dihydropyran core for oleuropein based secoiridoids
Vedachalam, Seenuvasan,Murugesh, Nithya,Chakraborty, Priyanka,Karvembu, Ramasamy,Liu, Xue-Wei
, p. 1832 - 1839 (2018/02/09)
We present the short synthesis of the suitably functionalized enantioselective dihydropyran core of secoiridoids using an N-heterocyclic carbene (NHC) catalyzed Coates-Claisen rearrangement mechanism. The key steps of the synthesis are (i) the highly enantioselective NHC catalyzed Coates-Claisen rearrangement for the dihydropyran core, (ii) the assembly of the target dihydropyran core structure of oleuropein from a highly diastereoselective exocyclic trans alkene, and (iii) the highly stereoselective assembly of a monoterpene elenolide core structure.
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.
Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A
Khong, Duc Thinh,Judeh, Zaher M.A.
, p. 109 - 111 (2016/12/23)
A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at O-6.
Preparation of primary amines by the alkylation of O-sulfonyloximes of benzophenone derivatives with Grignard reagents
Tsutsui, Hironori,Ichikawa, Tomoko,Narasaka, Koichi
, p. 1869 - 1878 (2007/10/03)
Primary amines are prepared by the electrophilic amination of Grignard reagents with benzophenone O-sulfonyloxime derivatives. 4,4'- Bis(trifluoromethyl)benzophenone O-sulfonyloximes react with alkyl Grignard reagents in the presence of a catalytic amount of CuCN in tetrahydrofuran- hexamethylphosphoric triamide to give N-alkylimines, which are readily hydrolyzed to primary amines. 3,3',5,5'-Tetrakis(trifluoromethyl)benzophenone O-p-tolylsulfonyloxime is arylated to the corresponding N-arylimines with aryl Grignard reagents in ether-toluene, and hydrolysis of the resulting imines gives aniline derivatives.
Synthesis of verbascoside: A dihydroxyphenylethyl glycoside with diverse bioactivity
Duynstee, Howard I.,De Koning, Martijn C.,Ovaa, Huib,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 2623 - 2632 (2007/10/03)
TMSOTf-mediated condensation of ethyl 4,6-O-benzylidene-1-thio-β-D- glucopyranoside (2) with peracetylated α-L-rhamnopyranosyl trichloroacetimidate donor 3a resulted in the formation of orthoester 4, which, after acetylation, rearranged into ethyl 3-O-(α-L-rhamnopyranosyl)-l- thio-β-D-glucopyranoside derivative 6a. The latter compound was converted into the corresponding trichloroacetimidate donors 8a-b. An alternative approach to trichloroacetimidate 8c commenced with the iodonium ion mediated glycosidation of ethyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranside (15) with 1,2:5,6-diisopropylidene-D-glucofuranose (16) to afford disaccharide 17, which was transformed into 8c in five steps. Condensation of 8a-c with 2- [3,4-di-(tert-butyldimethylsilyloxy)phenyl]ethanol (12) gave, after deacylation, key intermediate 14. Protecting-group manipulation of 14 and subsequent esterification of resulting 22 with 3,4-di-O-tert- butyldimethylsilylcaffeic acid (27) gave, after deprotection, verbascoside (1).
