5396-64-5Relevant articles and documents
Salvianolic acid I: A new depside from Salvia cavaleriei
Zhang,Li
, p. 70 - 72 (1994)
A new depside named salvianolic acid I was isolated from the aqueous extract of Salvia cavaleriei, along with salvianolic acids A, B, C, H, isosalvianolic acid C, lithospermic acid, and rosmarinic acid. The chemical structures were determined by spectral
A TETRACYCLIC TRITERPENE LACTONE AND OTHER CONSTITUENTS FROM THE BARK OF ABIES FIRMA
Tanaka, Reiko,Inosiri, Atsuyo,Yoneda, Michiko,Ishida, Toshimasa,Numada, Atsushi,et al.
, p. 3263 - 3265 (1990)
The stem bark of Abies firma contained five n-fatty acids having C22-C26, campesterol, β-sitosterol, five n-alkyl ferulates bearing alkyl groups from C22 to C26 and a new tetracyclic triterpene lactone, for which the structure was established as 3-oxo-9β-lanosta-7,24-dien-26,23R-olide by single crystal X-ray analysis.
Characterization by LC-MSn of four new classes of chlorogenic acids in green coffee beans: Dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl- dimethoxycinnamoylquinic acids
Clifford, Michael N.,Knight, Susan,Surucu, Birgul,Kuhnert, Nikolai
, p. 1957 - 1969 (2006)
LC-MS4 has been used to detect and characterize in green coffee beans 12 chlorogenic acids not previously reported in nature. These comprise three isomeric dimethoxycinnamoylquinic acids (7-9) (Mr 382), three caffeoyl-dimethoxycinnam
Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
Ojha, Subhadra,Panda, Niranjan
supporting information, p. 1292 - 1298 (2022/02/19)
A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
Covalent Inhibition of Bacterial Urease by Bifunctional Catechol-Based Phosphonates and Phosphinates
Pagoni, Aikaterini,Grabowiecka, Agnieszka,Tabor, Wojciech,Mucha, Artur,Vassiliou, Stamatia,Berlicki, ?ukasz
supporting information, p. 404 - 416 (2021/01/13)
In this study, a new class of bifunctional inhibitors of bacterial ureases, important molecular targets for antimicrobial therapies, was developed. The structures of the inhibitors consist of a combination of a phosphonate or (2-carboxyethyl)phosphinate functionality with a catechol-based fragment, which are designed for complexation of the catalytic nickel ions and covalent bonding with the thiol group of Cys322, respectively. Compounds with three types of frameworks, including β-3,4-dihydroxyphenyl-, α-3,4-dihydroxybenzyl-, and α-3,4-dihydroxybenzylidene-substituted derivatives, exhibited complex and varying structure-dependent kinetics of inhibition. Among irreversible binders, methyl β-(3,4-dihydroxyphenyl)-β-(2-carboxyethyl)phosphorylpropionate was observed to be a remarkably reactive inhibitor of Sporosarcina pasteurii urease (kinact/KI = 10 420 s-1 M-1). The high potential of this group of compounds was also confirmed in Proteus mirabilis whole-cell-based inhibition assays. Some compounds followed slow-binding and reversible kinetics, e.g., methyl β-(3,4-dihydroxyphenyl)-β-phosphonopropionate, with Ki? = 0.13 μM, and an atypical low dissociation rate (residence time τ = 205 min).
Design and synthesis of dual active neovibsanin derivatives based on a chemical structure merging method
Fukuyama, Yoshiyasu,Imagawa, Hiroshi,Kasai, Yusuke,Kishimoto, Suguru,Kubo, Miwa,Matsui, Nobuaki,Yamamoto, Hirofumi,Yanagimoto, Tsuyoshi
supporting information, (2020/08/19)
A hybrid compound consisting of neovibsanin and trans-banglene was designed according to a structure merging method and synthesized via a sequence of key steps including a Diels–Alder cycloaddition, stereoselective alkynylation, and intramolecular oxa-Mic
Enantioselective Total Syntheses of Pallambins A–D
Zhang, Xiwu,Cai, Xinxian,Huang, Bin,Guo, Lei,Gao, Zhongrun,Jia, Yanxing
, p. 13380 - 13384 (2019/08/16)
The first enantioselective total syntheses of (?)-pallambins A–D have been achieved in 15 or 16 steps from a known chiral cyclohexenone. Salient features of the syntheses include a palladium-catalyzed oxidative cyclization to assemble the [3.2.1]bicyclic moiety, an Eschenmoser–Claisen rearrangement/lactone formation sequence to construct the C ring, an intramolecular Wittig reaction to form the D ring, and individual transformations of pallambins C and D to generate pallambins A and B. The described synthesis avoids protecting-group manipulations through the design of highly chemo- and stereoselective transformations. During the course of this work, a palladium-catalyzed method for the dehydrobromination of α-bromoketones was developed, and the scope of this transformation was also investigated.
Natural product derivatization with β-lactones, β-lactams and epoxides toward ‘infinite’ binders
Jouanneau, Morgan,Vellalath, Sreekumar,Kang, Guowei,Romo, Daniel
supporting information, p. 3348 - 3354 (2019/05/17)
β-Lactones, β-lactams and epoxides are privileged structural motifs found in both therapeutics and natural products. Herein we report several strategies for annulation of these motifs onto natural products that are not known to covalently modify their cellular targets. These strategies can facilitate identification of previously unidentified cellular targets or identify novel cellular targets of these natural products. The reported strategies include telescoped synthesis of β-lactones from allylic alcohols, nucleophile-catalyzed Michael aldol-β-lactonizations, and [2 + 2] β-lactam annulations with complex, commercially available alkene-containing natural products as substrates. A novel method for the tagging of phenolic natural products with epoxides is also reported.
In-vitro and in-vivo antimalarial activity of caffeic acid and some of its derivatives
Alson, Sylvain G.,Jansen, Olivia,Cieckiewicz, Ewa,Rakotoarimanana, Hajatiana,Rafatro, Herintsoa,Degotte, Gilles,Francotte, Pierre,Frederich, Michel
, p. 1349 - 1356 (2018/07/31)
Objectives: To explore the in-vitro and in-vivo antimalarial potential of caffeic acid and derivatives. Methods: Two common phenolic acids (caffeic acid and chlorogenic acid) were evaluated for in-vitro and in-vivo antiplasmodial activity in comparison with some semi-synthetic derivatives that were synthesized. An in-vitro assay based on plasmodial lactate dehydrogenase activity, and the classical in-vivo 5-day suppressive test from Peters on an artemisinin-resistant Plasmodium berghei strain was used. Parasitic stage sensitivity to ethyl caffeate was determined in this work. Key findings: Phenolic acid esters derivatives showed better antiplasmodial activity than corresponding phenolic acids. The derivative with the highest in-vitro activity being caffeic acid ethyl ester, exhibiting an IC50?=?21.9?±?9.4?μm. Ethyl caffeate and methyl caffeate were then evaluated for antimalarial activity in?vivo and ethyl caffeate showed a growth inhibition of 55% at 100?mg/kg. Finally, it seems that ethyl caffeate blocks the growth of young parasitic forms. Conclusions: Our study provides evidence for an antimalarial potential of caffeic acid derivatives which are common in several medicinal plants traditionally used against malaria. It also demonstrates the possibility to use such derivatives in the treatment of malaria.
SCAPHOPETALONE ANALOGS AND THEIR USES
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Page/Page column 24, (2017/05/10)
The present disclosure relates to scaphopetalone analogs, methods of making the analogs, and their medicinal uses.
