Atropisomerism Observed in Indometacin Derivatives
Organic Letters2011Vol. 13(4), pp. 760–763
Citations Over TimeTop 10% of 2011 papers
Hideyo Takahashi, Shintaro Wakamatsu, Hidetsugu Tabata, Tetsuta Oshitari, Ayako Harada, Keizo Inoue, Hideaki Natsugari
Abstract
To elucidate the active conformation of indometacin that differentiates between cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), the stereochemistry around the N-benzoylated indole moiety of indometacin was studied. Resolution of stable atropisomers as representative conformations was found to be possible by restricting rotation about the N-C7' and/or C7'-C1' bond. Only the aR-isomer showed specific inhibition of COX-1, and COX-2 was not inhibited by either atropisomer.
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