38002-48-1Relevant articles and documents
Aminium cation-radical catalysed selective hydration of (E)-aryl enynes
Giel, Marie-Claire,Barrow, Andrew S.,Smedley, Christopher J.,Lewis, William,Moses, John E.
supporting information, p. 6991 - 6994 (2021/07/21)
The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, we report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biologically important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.
Triazole-curcuminoids: A new class of derivatives for 'tuning' curcumin bioactivities?
Caprioglio, Diego,Torretta, Simone,Ferrari, Maila,Travelli, Cristina,Grolla, Ambra A.,Condorelli, Fabrizio,Genazzani, Armando A.,Minassi, Alberto
, p. 140 - 152 (2015/12/31)
Curcumin is a unique blend of pharmacophores responsible for the pleiotropy of this natural pigment. In the present study we have replaced the 1,3-dicarbonyl moiety with a 1,2,3-triazole ring to furnish a new class of triazole-curcuminoids as a possible strategy to generate new compounds with different potency and selectivity compared to curcumin. We obtained a proof-of-principle library of 28 compounds tested for their cytotoxicity (SY-SY5Y and HeLa cells) and for their ability to inhibit NF-κB. Furthermore, we also generated 1,3-dicarbonyl curcuminoids of selected click compounds. Triazole-curcuminoids lost their ability to be Michael's acceptors, yet maintained some of the features of the parent compounds and disclosed new ones. In particular, we found that some compounds were able to inhibit NF-κB without showing cytotoxicity, while others, unlike curcumin, activated NF-κB signalling. This validates the hypothesis that click libraries can be used to investigate the biological activities of curcumin as well as generate analogs with selected features.
Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes via Visible Light Photocatalysis
Nguyen, Theresa H.,Morris, Scott A.,Zheng, Nan
supporting information, p. 2831 - 2837 (2016/02/18)
One-step syntheses of carbocycles substituted with amines from simple starting materials remain rare. We recently developed an intermolecular [3+2] annulation of cyclopropylanilines with alkenes and alkynes that enables this one-step synthesis. Herein, we
