130688-84-5Relevant academic research and scientific papers
Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells
Perjesi, Pal,Das, Umashankar,De Clercq, Erik,Balzarini, Jan,Kawase, Masame,Sakagami, Hiroshi,Stables, James P.,Lorand, Tamas,Rozmer, Zsuzsanna,Dimmock, Jonathan R.
, p. 839 - 845 (2008)
A series of 3-benzylidene-4-chromanones 1a-l were prepared and their cytotoxicity towards human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 lymphoid leukemia cells were compared to the previously generated biodata in these three assays for the
Rhodium-Catalyzed Asymmetric Transfer Hydrogenation/Dynamic Kinetic Resolution of 3-Benzylidene-Chromanones
Molina Betancourt, Ricardo,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie
supporting information, p. 1621 - 1625 (2021/03/08)
Straightforward access to enantiomerically enriched cis-3-benzyl-chromanols from (E)-3-benzylidene-chromanones was developed through Rh-catalyzed asymmetric transfer hydrogenation. This transformation allowed the reduction of both the CaC and CaO bonds and the formation of two stereocenters in high yields with excellent levels of diastereo- A nd enantioselectivities (up to >99:1 dr, up to >99% ee) in a single step through a dynamic kinetic resolution process using a low catalyst loading and HCO2H/DABCO as the hydrogen source.
Tetralone derivatives are MIF tautomerase inhibitors and attenuate macrophage activation and amplify the hypothermic response in endotoxemic mice
?rfi, László,Bagóné Vántus, Viola,Garai, János,Garami, András,Jakus, Péter Balázs,Kéringer, Patrik,Kovács, Dominika,Krekó, Marcell,Lóránd, Tamás,Radnai, Balázs,Rumbus, Zoltán,Vámos, Eszter
, p. 1357 - 1369 (2021/07/22)
Macrophage migration inhibitory factor (MIF) is a pro-inflammatory cytokine playing crucial role in immunity. MIF exerts a unique tautomerase enzymatic activity that has relevance concerning its multiple functions and its small molecule inhibitors have been proven to block its pro-inflammatory effects. Here we demonstrate that some of the E-2-arylmethylene-1-tetralones and their heteroanalogues efficiently bind to MIF’s active site and inhibit MIF tautomeric (enolase, ketolase activity) functions. A small set of the synthesised derivatives, namely compounds (4), (23), (24), (26) and (32), reduced inflammatory macrophage activation. Two of the selected compounds (24) and (26), however, markedly inhibited ROS and nitrite production, NF-κB activation, TNF-α, IL-6 and CCL-2 cytokine expression. Pre-treatment of mice with compound (24) exaggerated the hypothermic response to high dose of bacterial endotoxin. Our experiments suggest that tetralones and their derivatives inhibit MIF’s tautomeric functions and regulate macrophage activation and thermal changes in severe forms of systemic inflammation.
