- Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor
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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.
- Nakao, Syuhei,Mabuchi, Miyuki,Wang, Shenglan,Kogure, Yoko,Shimizu, Tadashi,Noguchi, Koichi,Tanaka, Akito,Dai, Yi
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p. 3167 - 3172
(2017/06/13)
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- New classes of Gram-positive selective antibacterials: Inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis
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An antimicrobial phenolic stilbene, (E)-3-hydroxy-5-methoxystilbene, 1 was recently isolated from the leaves of Comptonia peregrina (L.) Coulter and shown to possess inhibitory activity against several Gram-positive bacteria, including isolates of methici
- Kabir, M. Shahjahan,Engelbrecht, Kathleen,Polanowski, Rebecca,Krueger, Sarah M.,Ignasiak, Rachel,Rott, Marc,Schwan, William R.,Stemper, Mary E.,Reed, Kurt D.,Sherman, David,Cook, James M.,Monte, Aaron
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scheme or table
p. 5745 - 5749
(2009/06/18)
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- An efficient palladium-catalyzed Negishi cross-coupling reaction with arylvinyl iodides: facile regioselective synthesis of E-stilbenes and their analogues
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A general synthetic route for the Pd-catalyzed cross-coupling of an arylzinc reagent with arylvinyl iodides (Negishi cross-coupling) has been developed. The system permits efficient and selective preparation of E-stilbenes and their analogues. It also functions effectively at low levels of catalyst loading without the need for an additional ligand and tolerates a wide range of functional groups including heteroaromatic substrates. A systematic study of various parameters was performed and correlated with catalyst-substrate activity.
- Kabir, M. Shahjahan,Monte, Aaron,Cook, James M.
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p. 7269 - 7273
(2008/03/13)
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- Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells
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The inhibitory effects of pinosylvin analogues on the production of COX-2 mediated PGE2 were evaluated in a cell culture system. A new series of potential inhibitors, including 3-hydroxy-5-benzyloxy-trans-stilbene and 3,5-dimethoxy-trans-stilbene, have been identified. A series of natural stilbenoids, pinosylvin and its derivatives, were synthesized and evaluated for the inhibitory activity of prostaglandin E2 production in lipopolysaccharide-induced RAW 264.7 cells. Potential inhibitors, including 3,5-dimethoxy-trans-stilbene and 3-hydroxy-5-benzyloxy-trans-stilbene, have been newly identified, and thus providing chemical leads for the further development of anti-inflammatory or cancer chemopreventive agents.
- Park, Eun-Jung,Min, Hye-Young,Ahn, Yong-Hyun,Bae, Cheol-Man,Pyee, Jae-Ho,Lee, Sang Kook
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p. 5895 - 5898
(2007/10/03)
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- Pest control chemicals against pine wood nematodes
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Disclosed are (1) pest control chemicals against the pine wood nematodes containing an extract from a pine tree with an organic solvent, (2) a repellent against the pine wood nematodes containing α-humulene or a mixture of α-humulene and β-bisabolene, (3) a repellent against the pine wood nematodes containing a mixture of α-pinene and calarene, (4) a nematicide against the pine wood nematodes containing methyl ferulate, (+)-pinoresinol or a mixture thereof, and (5) highly effective pest control chemicals against pine wood nematodes containing hydroxystilbenes or salts thereof which are prepared by synthesizing methoxystilbenes from benzyl phosphonates and methoxybenzaldehydes by a Wittig-Horner reaction, performing demethylation to obtain the hydroxystilbenes, and preparing the salts thereof by conventional methods if necessary.
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- Synthesis and nematocidal activity of hydroxystilbenes
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Various (E)-hydroxystilbenes were synthesized from (E)/(Z) mixtures of methoxystilbenes through a new (Z)-(E) isomerization method followed by demethylation. The nematocidal activity appears when methoxystilbenes are demethylated to hydroxystilbenes. For this activity, a hydroxy group at the C-2 or C-3 position is necessary. Thus, 2-hydroxy-, 3-hydroxy-, 2,6-dihydroxy-, 3,4-dihydroxy-, 3,5-dihydroxy-, 2,2'-dihydroxy-, 3,3'-dihydroxy-, 3,4'dihydroxy-, 2-hydroxy-4-methoxy-, 5-hydroxy-2-methoxy-, 2-hydroxy-6-methoxy-, 6-allyloxy-2-hydroxy-, 3-hydroxy-5-methoxy-, and 5-allyloxy-3-hydroxystilbenes showed rather potent nematocidal activity. The activity of 5-allyloxy-3-hydroxystilbene was the strongest [minimal lethal concentration (MLC) = 30 μM]. The activities of the (E) and (Z) isomers were comparable. The activities were also retained, though they were weaker, in the dihydro derivatives, hydroxybibenzyls.
- Ali,Kondo,Tsuda
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p. 1130 - 1136
(2007/10/02)
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