33617-49-1Relevant academic research and scientific papers
Design and synthesis of π-extended resveratrol analogues and in vitro antioxidant and anti-inflammatory activity evaluation
Damodar, Kongara,Gim, Ji Geun,Jeon, Seong Ho,Lee, Jeong Tae,Lee, Yeontaek,Nam, Ki Yoon,Park, Jae Phil,Park, Lee Seul
, (2021/06/14)
The research on resveratrol (1) has been conducted intensively over a long time due to its proven antioxidant activity and disease-fighting capabilities. Many efforts have also been made to increase these biological effects. In the present study, six new extended aromatic resveratrol analogues containing naphthalene (2) and its bioisosteres quinoline (3 and 4), isoquinoline (5) quinoxaline (6) and quinazoline (7) scaffolds were designed and synthesized using an annulation strategy. The antioxidant and anti-inflammatory activities of these compounds were investigated. All compounds showed better antioxidant activity than resveratrol in ABTS assay. As for the anti-inflammatory test, 5 and 7 exhibited better activity than resveratrol. It is worth noting that nitrogen substitution on the extended aromatic resveratrol analogues has a significant impact on cell viability. Taking the antioxidant activities and NO inhibition activities into consideration, we conclude that isoquinoline analogue 5 may qualify for the further investigation of antioxidant and anti-inflammatory therapy. Furthermore, our study results suggest that in order to improve the biological activity of polyphenolic compounds, extended aromaticity and nitrogen substitution strategy could be a viable method for the design of future drug candidates.
Arylmethyl phosphonate preparation method
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Paragraph 0024; 0025, (2017/01/02)
The invention provides an arylmethyl phosphonate preparation method. The method includes the following steps that arylmethyl ester, triethyl phosphate and a catalyst are sequentially added into a reactor and reacted for 5-8 h at the temperature of 100-200 DEG C after full stirring, and after excessive triethyl phosphate is distilled off through decompression, the mixture continues to be reacted for 3-7 h at the temperature of 100-200 DEG C; then, the mixture is cooled to the room temperature, a product is extracted through a mixed solvent, and arylmethyl phosphonate is obtained after the mixed solvent is removed. The catalyst is one or more of tetramethyl ammonium bromide, tetraethylammonium bromide, tetrabutyl ammonium bromide, benzyltrimethyl ammonium bromide, cetyl trimethyl ammonium bromide, cetyltrimethyl ammonium chloride, ammonium chloride, sodium iodide and potassium iodide. Arylmethyl phosphonate is synthesized through a one-step method, other solvents are not added, operation is easy, and the product yield is high and can be 85.3% at maximum.
Dimerization of piceatannol by Momordica charantia peroxidase and α-glucosidase inhibitory activity of the biotransformation products
Wan, Xiang,Wang, Xiao-Bing,Yang, Ming-Hua,Wang, Jun-Song,Kong, Ling-Yi
, p. 5085 - 5092 (2011/10/08)
Stilbenes, especially those oligomers, have great potential to be antihyperglycemic agents. In this study, eight stilbene dimers, including five new ones, were obtained by biotransformation of piceatannol using Momordica charantia peroxidase (MCP) for the first time. Their structures were established on the basis of spectroscopic evidences. These piceatannol dimers displayed potential α-glucosidase inhibitory activities, and trans double bond, tetrahydrofuran ring, and free adjacent phenolic dihydroxyls were found to be important for their activities. Enzymatic biotransformation of stilbenes by M. charantia peroxidase (MCP) was showed to be a prominent way to produce oligomeric stilbenes for antihyperglycemic development.
Syntheses of resveratrol and its hydroxylated derivatives as radical scavenger and tyrosinase inhibitor
Lee, Hyun Suck,Lee, Byung Won,Kim, Mi Ran,Jun, Jong-Gab
experimental part, p. 971 - 975 (2010/10/21)
Eight hydroxylated stilbene derivatives including resveratrol, desoxyrhapontigenin and piceatannol as potential radical scavenger and tyrosinase inhibitor are synthesized using optimized Wittig-Horner reaction for excellent trans-selectivity in good yields. Antioxidant activity was tested against ABTS radical and tyrosinase inhibitory activity was performed with L-tyrosine as the substrate based on previous procedure with some modification. In general, catecholic stilbenes showed stronger activity against ABTS radical and resorcinolic moiety showed stronger tyrosinase inhibitory activity. Synthetic piceatannol which containing both catecholic and resorcinolic moieties showed the strongest activity in both as ABTS radical scavenger and tyrosinase inhibitor with IC50 values of 4.1 and 8.6 μM, respectively.
Efficient total synthesis of piceatannol via (e)-selective wittig-horner reaction
Young Han, Su,Suck Lee, Hyun,Hye Choi, Da,Woon Hwang, Jung,Mo Yang, Deok,Jun, Jong-Gab
experimental part, p. 1425 - 1432 (2009/09/30)
Efficient and practical total synthesis of piceatannol via (E)-selective Wittig-Horner reaction is demonstrated with six steps in overall 40% yield from a commercially available, cheap starting material, 3,5-dihydroxybenzoic acid. Wittig-Horner reaction o
Effect of methyl substitution on the antioxidative property and genotoxicity of resveratrol
Fukuhara, Kiyoshi,Nakanishi, Ikuo,Matsuoka, Atsuko,Matsumura, Tomohiro,Honda, Sachiko,Hayashi, Mikiko,Ozawa, Toshihiko,Miyata, Naoki,Saito, Shinichi,Ikota, Nobuo,Okuda, Haruhiro
, p. 282 - 287 (2008/12/22)
Resveratrol (trans-3,4′,5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4′-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4′-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.
Synthesis of a piceatannol analog: Replacement of hydroxy group with amide functionality
Venkatachalam,Huang,Yu,Uckun
, p. 1489 - 1497 (2007/10/03)
Polyhydroxylated stilbene analogs of piceatannol are shown to possess protein-tyrosine kinase (PTK) inbibitory activity. We have developed a novel approach to introduce an amide moiety into the structure of piceatannol. The amido substituted stilbene deri
Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol
Thakkar, Kshitij,Geahlen, Robert L.,Cushman, Mark
, p. 2950 - 2955 (2007/10/02)
A series of hydroxylated trans-stilbene related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxy stilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function.A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product.Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly.The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.
Synthesis of bryophyte components 2. Syntheses of prenylated bibenzyl derivatives
Eicher,Tiefensee,Donig,Pick
, p. 98 - 102 (2007/10/02)
Efficient and expeditious syntheses of the biologically active prenylated bibenzyl derivatives 1a-d are developed giving rise to their access on a preparative scale.
