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Conformation and atropisomeric properties of indometacin derivatives.

Wakamatsu, Shintaro; Takahashi, Yuka; Tabata, Hidetsugu; Oshitari, Tetsuta; Tani, Norihiko; Azumaya, Isao; Katsumoto, Yukiteru; Tanaka, Takeyuki; Hosoi, Shinzo; Natsugari, Hideaki; Takahashi, Hideyo.
Chemistry; 19(22): 7056-63, 2013 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-23576314
The stereochemistry around the N-benzoylated indole moiety of indometacin was studied by restricting the rotation about the N-C7' and/or C7'-C1' bond. In the 2',6'-disubstituted ones, an atropisomeric property was found and the atropoisomers were separated and isolated as stable forms. Their biological abilities to inhibit cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) were examined. Only the aR-isomer showed specific inhibition of COX-1, and COX-2 was not inhibited by either atropisomer. Conformational analysis in NMR studies and X-ray crystallography, and CD spectra in combination with calculations were utilized to elucidate the bioactive conformations.