- N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites
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The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators has not been fully elucidated. N-Cinnamoylanthranilic acid derivatives (CADs) contain structural elements from the TRPA1 modulators cinnamaldehyde and flufenamic acid, so it was hypothesized that specific modulators could be found amongst them and more could be learnt about modulation of TRPA1 with these compounds. A series of CADs was therefore screened for agonism and antagonism in HEK293 cells stably transfected with WT-human (h)TRPA1, or C621A, F909A or F944A mutant hTRPA1. Derivatives with electron-withdrawing and/or electron-donating substituents were found to possess different activities. CADs with inductive electron-withdrawing groups were agonists with desensitising effects, and CADs with electron-donating groups were either partial agonists or antagonists. Site-directed mutagenesis revealed that the CADs do not undergo conjugate addition reaction with TRPA1, and that F944 is a key residue involved in the non-covalent modulation of TRPA1 by CADs, as well as many other structurally distinct non-reactive TRPA1 ligands already reported.
- Chandrabalan, Arundhasa,McPhillie, Martin J.,Morice, Alyn H.,Boa, Andrew N.,Sadofsky, Laura R.
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p. 141 - 156
(2019/03/17)
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- Preparation method of avenanthramide and derivative thereof
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The invention provides a preparation method of avenanthramide and a derivative thereof. The avenanthramide and the derivative thereof are synthesized and obtained by mainly utilizing an organic acid and aminobenzoic acid as major reactants. The method is
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Paragraph 0020
(2017/08/19)
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- Key Phytochemicals Contributing to the Bitter Off-Taste of Oat (Avena sativa L.)
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Sensory-directed fractionation of extracts prepared from oat flour (Avena sativa L.) followed by LC-TOF-MS, LC-MS/MS, and 1D/2D-NMR experiments revealed avenanthramides and saponins as the key phytochemicals contributing to the typical astringent and bitter off-taste of oat. Besides avenacosides A and B, two previously unreported bitter-tasting bidesmosidic saponins were identified, namely, 3-(O-α-l-rhamnopyranosyl(1→2)-[β-d-glucopyranosyl(1→3)-β-d-glucopyranosyl(1→4)]-β-d-glucopyranosid)-26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22,26-triol, and 3-(O-α-l-rhamnopyranosyl(1→2)-[β-d-glucopyranosyl(1→4)]-β-d-glucopyranosid)-26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22,26-triol. Depending on the chemical structure of the saponins and avenanthramides, sensory studies revealed human orosensory recognition thresholds of these phytochemicals to range between 3 and 170 μmol/L.
- Günther-Jordanland, Kirsten,Dawid, Corinna,Dietz, Maximilian,Hofmann, Thomas
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p. 9639 - 9652
(2017/01/12)
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- COMBINATION THERAPY OF ARTHRITIS WITH TRANILAST
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Combination therapy is disclosed herein for the treatment an arthritic condition (e.g. rheumatoid arthritis, osteoarthritis or psoriatic arthritis). The therapies disclosed herein comprise administering tranilast or an analogous compound in combination wi
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- A simple two-step synthesis of avenanthramides, constituents of oats (Avena sativa L)
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A simple two-step general procedure has been developed to prepare naturally occurring and synthetic avenanthramides, constituents of oats (Avena sativa L). Reaction of anthranilic acid 1 with Meldrum's acid 2 gives half amide of malonic acid 3 which on condensation with different benzaldehyde derivatives 4a-m gives avenanthramides 5a-m of which 5a-d are natural, 5e-g are their methyl ethers and 5h-m are synthetic.
- Kamat, Shrivallabh P.,Parab, Sulaksha J.
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p. 2074 - 2078
(2008/09/19)
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- Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships
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Eight avenanthramides, amides of anthranilic acid (1) and 5-hydroxyanthranilic acid (2), respectively, and the four cinnamic acids p-coumaric (p), caffeic (c), ferulic (f), and sinapic (s) acid, were synthesized for identification in oat extracts and for structure-antioxidant activity studies. Three compounds (2p, 2c, and 2f) were found in oat extracts. As assessed by the reactivity toward 1,1-diphenyl-2-picrylhydrazyl (DPPH), all avenanthramides except 1p showed activity. Initially, the antioxidant activity of the avenanthramides decreased in a similar order as for the corresponding cinnamic acids, that is: sinapic > caffeic > ferulic > p-coumaric acid. The avenanthramides derived from 2 were usually slightly more active than those derived from 1. All avenanthramides inhibited azo-initiated peroxidation of linoleic acid. 1c and 1s were initially the most effective compounds. The relative order of antioxidant activities was slightly different for the DPPH and the linoleic acid assays run in methanol and chlorobenzene, respectively.
- Bratt, Katarina,Sunnerheim, Kerstin,Bryngelsson, Susanne,Fagerlund, Amelie,Engman, Lars,Andersson, Rolf E.,Dimberg, Lena H.
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p. 594 - 600
(2007/10/03)
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- The Phytoalexins of Oat Leaves: 4H-3,1-Benzoxazin-4-ones or Amides?
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Synthetic evidence is presented that the major phytoalexin of oat leaves is not the 4H-3,1-benzoxazin-4-one previously reported, but the corresponding amide.Other oat and carnation phytoalexins are prepared.
- Crombie, Leslie,Mistry, Jayshree
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p. 2647 - 2648
(2007/10/02)
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- Aromatic carboxylic amide derivatives
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Novel aromatic carboxylic amides of the general formula: EQU1 wherein each of R1 and R2 is a hydrogen atom or an alkyl group having 1-4 carbon atoms, R3 and R4 are hydrogen atoms or together form another chemical bond, each X is a hydroxyl group, a halogen atom, an alkyl group having 1-4 carbon atoms and an alkoxy group containing 1-4 carbon atoms, and n is an integer of 1-3, with the proviso that when two Xs are alkyl or alkoxy groups, they may be connected together to form a ring, as well as pharmaceutically acceptable salts thereof. These compounds possess a strong antiallergenic action and are thus useful for treatment of asthma, hay fever, anticaria and atopic dermatitis. The above aromatic carboxylic amides can be prepared by reacting a reactive functional derivative of the general formula: EQU2 wherein R1, R2, R3, R4, X and n have the same meanings given above, with an aminobenzoic acid of the formula: And, if desired, converting the resulting amide into the corresponding salts.
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