61566-33-4Relevant academic research and scientific papers
Exploring the fatty acid amide hydrolase and cyclooxygenase inhibitory properties of novel amide derivatives of ibuprofen
Catalanotti, Bruno,Deplano, Alessandro,Fowler, Christopher J.,Karlsson, Jessica,Moraca, Federica,Onnis, Valentina,Svensson, Mona
, p. 815 - 823 (2020/04/02)
Inhibition of fatty acid amide hydrolase (FAAH) reduces the gastrointestinal damage produced by non-steroidal anti-inflammatory agents such as sulindac and indomethacin in experimental animals, suggesting that a dual-action FAAH-cyclooxygenase (COX) inhib
Substrate-selective inhibition of cyclooxygenase-2: Development and evaluation of achiral profen probes
Windsor, Matthew A.,Hermanson, Daniel J.,Kingsley, Philip J.,Xu, Shu,Crews, Brenda C.,Ho, Winnie,Keenan, Catherine M.,Banerjee, Surajit,Sharkey, Keith A.,Marnett, Lawrence J.
, p. 759 - 763 (2012/10/29)
Cyclooxygenase-2 (COX-2) oxygenates arachidonic acid and the endocannabinoids 2-arachidonoylglycerol (2-AG) and arachidonoylethanolamide (AEA). We recently reported that (R)-profens selectively inhibit endocannabinoid oxygenation but not arachidonic acid oxygenation. In this work, we synthesized achiral derivatives of five profen scaffolds and evaluated them for substrate-selective inhibition using in vitro and cellular assays. The size of the substituents dictated the inhibitory strength of the analogs, with smaller substituents enabling greater potency but less selectivity. Inhibitors based on the flurbiprofen scaffold possessed the greatest potency and selectivity, with desmethylflurbiprofen (3a) exhibiting an IC50 of 0.11 μM for inhibition of 2-AG oxygenation. The crystal structure of desmethylflurbiprofen complexed to mCOX-2 demonstrated a similar binding mode to other profens. Desmethylflurbiprofen exhibited a half-life in mice comparable to that of ibuprofen. The data presented suggest that achiral profens can act as lead molecules toward in vivo probes of substrate-selective COX-2 inhibition.
Ene reductase-catalysed synthesis of (R)-profen derivatives
Pietruszka, Joerg,Schoelzel, Melanie
scheme or table, p. 751 - 756 (2012/04/23)
Enantiomerically pure (R)-profen derivatives and intermediates are synthesised utilising the enzyme YqjM, an ene reductase from Bacillus subtilis. After optimisation of the reaction conditions, the chemoenzymatic approach was applied for the first time in the synthesis of (R)-flurbiprofen methyl ester. Copyright
Asymmetric synthesis of ibuprofen via diastereoselective alkylation of a homochiral N-acylbornanesultam
Oppolzer, Wolfgang,Rosset, Stephane,De Brabander, Jef
, p. 1539 - 1540 (2007/10/03)
A very short, 4 step synthesis of 2-(4-isobutylphenyl)propionic acid (ibuprofen) was achieved in 57% overall. yield, using a highly diastereoselective alkylation of the chiral enolate derived from N-(4-isobutylphenyl)acetyl bornanesultam as a key step.
