115375-24-1Relevant academic research and scientific papers
Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D
Yan, Shiqiang,Ren, Sumei,Ding, Ning,Li, Yingxia
, p. 41 - 46 (2018)
Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3-NaBH4 system in one pot.
Prenylated trans-cinnamic esters and ethers against clinical fusarium spp.: Repositioning of natural compounds in antimicrobial discovery
Balmas, Virgilio,Carta, Paola,Casalini, Stefano,Chtioui, Wiem,Delogu, Giovanna,Dettori, Maria A.,Fabbri, Davide,Migheli, Quirico,Oufensou, Safa
, (2021/06/14)
Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 μM and 7.8–125 μM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.
A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives
Moni, Lisa,Banfi, Luca,Basso, Andrea,Mori, Alessia,Risso, Federica,Riva, Renata,Lambruschini, Chiara
, p. 1737 - 1749 (2021/03/23)
A thorough study on the (E) to (Z) photoisomerization of ferulic acid derivatives (esters, amides of all types, and ketones) was carried out. At the photostationary state, only aliphatic or benzylic tertiary amides reach a nearly complete conversion of (E) isomers into the (Z) ones, whereas for esters, primary and secondary amides or aromatic tertiary amides mixtures of (Z)/(E) ranging from 7 : 93 to 72 : 28 are observed. Ketones show rather limited photoisomerization. However, (Z) ketones may be obtained by the reaction of organometal compounds with an isomerized (Z) Weinreb amide.
Multicomponent, fragment-based synthesis of polyphenol-containing peptidomimetics and their inhibiting activity on beta-amyloid oligomerization
Lambruschini, Chiara,Galante, Denise,Moni, Lisa,Ferraro, Francesco,Gancia, Giulio,Riva, Renata,Traverso, Alessia,Banfi, Luca,D'Arrigo, Cristina
, p. 9331 - 9351 (2017/11/22)
A new and short fragment-based approach towards artificial (but "natural-based") complex polyphenols has been developed, exploiting the Ugi multicomponent reaction of phenol-containing simple substrates. The resulting library of compounds has been tested
First diastereoselective synthesis of methyl caffeoyl- and feruloyl-muco-quinates
Jaiswal, Rakesh,Dickman, Michael H.,Kuhnert, Nikolai
experimental part, p. 5266 - 5277 (2012/08/08)
We report on a diastereoselective synthesis of six derivatives of caffeoyl- and feruloyl-muco-quinic acids. All the muco-quinic acid derivatives were obtained in excellent yield in five steps starting from quinic acid, caffeic acid and ferulic acid. Allyl ether protection of trans-hydroxy cinnamic acids was here introduced to chlorogenic acids synthesis. We show that muco-quinic acid derivatives, which are formally diastereoisomers of chlorogenic acids, can be readily distinguished by their tandem mass spectra. The Royal Society of Chemistry 2012.
Total synthesis of the phenylpropanoid glycoside, grayanoside A
Zhang, San-Qi,Li, Zhong-Jun,Wang, An-Bang,Meng-Shen, Cai,Feng, Rui
, p. 281 - 285 (2007/10/03)
Grayanoside A, 2-(4-hydroxyphenyl)ethyl 6-O-feruloyl-β-D-glucopyranoside, was synthesized for the first time by using chloroacetyl groups for the protection of hydroxy functions. 2-(4-Allyloxyphenyl)ethyl 4-O-[(4-O-allyl)feruloyl]-2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside (12) was synthesized from 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside (8) in four steps with the goal of preparing syringalide B. It was found, however, that the feruloyl group migrated from the 4- to the 6-position of the glycopyranoside during the deprotection of 12.
