150258-84-7Relevant academic research and scientific papers
Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor
Nakao, Syuhei,Mabuchi, Miyuki,Wang, Shenglan,Kogure, Yoko,Shimizu, Tadashi,Noguchi, Koichi,Tanaka, Akito,Dai, Yi
, p. 3167 - 3172 (2017/06/13)
A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1?μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing HEK293 cells, as well as in rat dorsal root ganglia neurons by a whole cell patch clamp recording. Furthermore, pretreatment with 4z exhibited an analgesic effect on AITC-evoked TRPA1-related pain behavior in vivo.
A facile and rapid access to resveratrol derivatives and their radioprotective activity
Uzura, Saori,Sekine-Suzuki, Emiko,Nakanishi, Ikuo,Sonoda, Motohiro,Tanimori, Shinji
supporting information, p. 3886 - 3891 (2016/08/01)
A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes. The results revealed that some resveratrol derivatives efficiently protected the thymocytes from radiation-induced apoptosis.
Convenient One-Step Synthesis of Benzo[c]phenanthridines by Three-Component Reactions of Isochromenylium Tetrafluoroborates and Stilbenes in Acetonitrile
Chen, Gang-Gang,Wei, Jun-Qiang,Yang, Xiaoliang,Yao, Zhu-Jun
, p. 1502 - 1505 (2016/05/02)
A new type of three-component reaction of air-stable isochromenylium tetrafluoroborates with electron-rich stilbenes in acetonitrile has been developed under catalyst-free conditions in this work. This cascade multibond-formation reaction is initiated by an intermolecular oxa [4 + 2]-cycloaddition, relayed with a nucleophilic addition of acetonitrile, and terminated by an intramolecular Friedel-Crafts reaction, affording the corresponding benzo[c]phenanthridine analogues in one step.
Resveratrol derived butyrylcholinesterase inhibitors
Csuk, Rene,Albert, Sabrina,Kluge, Ralph,Stroehl, Dieter
, p. 499 - 503 (2013/07/26)
Novel polyhydroxylated (E)-stilbenes were synthesized by Mizoroki-Heck reactions and tested for their ability to inhibit the enzymes acetyl- and butyrylcholinesterase. Several of them are good inhibitors of butyrylcholinesterase; one of them carrying an extra fluorine substituent is a 94-fold stronger inhibitor of butyrylcholinesterase than of acetylcholinesterase. Novel polyhydroxylated (E)-stilbenes synthesized by Mizoroki-Heck reactions were tested for their ability to inhibit the enzymes acetyl- and butyrylcholinesterase. Several of them were found to be good inhibitors of butyrylcholinesterase. One of them carrying an extra fluorine substituent is a 94-fold stronger inhibitor of butyrylcholinesterase than of acetylcholinesterase.
Synthesis and antimicrobial activity of (E) stilbene derivatives
Albert, Sabrina,Horbach, Ralf,Deising, Holger B.,Siewert, Bianka,Csuk, René
, p. 5155 - 5166 (2011/10/04)
Plants use multiple defence mechanisms comprising both constitutive and inducible barriers to prevent entering of phytopathogenic micro-organisms. In many plant species one of the most efficient responses to combat attacking microbes is the rapid synthesis of antimicrobial low molecular weight phytoalexins, for example, resveratrol, 3,5,4′-trihydroxystilbene (1). Resveratrol and its natural derivatives, however, display only moderate antimicrobial effects. Nevertheless, resveratrol may be a useful lead structure for the chemical synthesis of antimicrobials. In this study, several series of stilbenes have been synthesized, starting from the aldehydes using Wittig reactions to access the corresponding styrenes that were subjected to Mizoroki-Heck reactions to yield the stilbenes in good yields. The stilbenes were tested in an agar diffusion assay against several bacteria and fungi. For some of these compounds the inhibiting zones for bacteria and fungi were comparable with those of the antibiotics tetracycline, streptomycin, ampicillin, or kanamycin, directed against prokaryotes, and nourseothricin or hygromycin controlling fungi, respectively.
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.
