- N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor
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A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R1 moiety and at the warhead, while the R2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone.
- Vallin, Karl S.A.,Sterky, Karin J.,Nyman, Eva,Bernstroem, Jenny,From, Rebecka,Linde, Christian,Minidis, Alexander B.E.,Nolting, Andreas,Naerhi, Katja,Santangelo, Ellen M.,Sehgelmeble, Fernando W.,Sohn, Daniel,Strindlund, Jennie,Weigelt, Dirk
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supporting information; experimental part
p. 5485 - 5492
(2012/09/22)
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- Aminoketone, oxazole and thiazole synthesis. Part XIII. 1 new 2-aryl-6-phenyloxazoles with 4-methyl or 4-isopropyl groups
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Benzoylation of (±)-α-alanine and (±)-valine followed by cyclization afforded the corresponding azlactones, which reacted with benzene, toluene, o- and m-xylene yielding substituted N-benzoyl-phenacylamines. Their cyclization in the presence of phosphorus oxychloride led to the title compounds whose electronic and NMR spectra (1H and 13C) are presented.
- Schiketanz, Iosif,Istrati, Daniela,Drǎghici, Constantin,Balaban, Alexandru T.
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p. 137 - 142
(2007/10/03)
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