24186-98-9Relevant articles and documents
Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis
Zheng, Jian,Swords, Wesley B.,Jung, Hoimin,Skubi, Kazimer L.,Kidd, Jesse B.,Meyer, Gerald J.,Baik, Mu-Hyun,Yoon, Tehshik P.
supporting information, p. 13625 - 13634 (2019/08/26)
Enantioselective catalysis of excited-state photoreactions remains a substantial challenge in synthetic chemistry, and intermolecular photoreactions have proven especially difficult to conduct in a stereocontrolled fashion. Herein, we report a highly enantioselective intermolecular [2 + 2] cycloaddition of 3-alkoxyquinolones catalyzed by a chiral hydrogen-bonding iridium photosensitizer. Enantioselectivities as high as 99% ee were measured in reactions with a range of maleimides and other electron-deficient alkene reaction partners. An array of kinetic, spectroscopic, and computational studies supports a mechanism in which the photocatalyst and quinolone form a hydrogen-bonded complex to control selectivity, yet upon photoexcitation of this complex, energy transfer sensitization of maleimide is preferred. The sensitized maleimide then reacts with the hydrogen-bonded quinolone-photocatalyst complex to afford a highly enantioenriched cycloadduct. This finding contradicts a long-standing tenet of enantioselective photochemistry that held that stereoselective photoreactions require strong preassociation to the sensitized substrate in order to overcome the short lifetimes of electronically excited organic molecules. This system therefore suggests that a broader range of alternate design strategies for asymmetric photocatalysis might be possible.
3-Hydroxyquinolin-2(1H)-ones as inhibitors of influenza A endonuclease
Sagong, Hye Yeon,Parhi, Ajit,Bauman, Joseph D.,Patel, Disha,Vijayan,Das, Kalyan,Arnold, Eddy,LaVoie, Edmond J.
supporting information, p. 547 - 550 (2013/07/26)
Several 3-hydroxyquinolin-2(1H)-ones derivatives were synthesized and evaluated as inhibitors of 2009 pandemic H1N1 influenza A endonuclease. All five of the monobrominated 3-hydroxyquinolin(1H)-2-ones derivatives were synthesized. Suzuki-coupling of p-fluorophenylboronic acid with each of these brominated derivatives provided the respective p-fluorophenyl 3-hydroxyquinolin(1H)-2-ones. In addition to 3-hydroxyquinolin-2(1H)-one, its 4-methyl, 4-phenyl, 4-methyl-7-(p-fluorophenyl), and 4-phenyl-7-(p-fluorophenyl) derivatives were also synthesized. Comparative studies on their relative activity revealed that both 6- and 7-(p-fluorophenyl)-3-hydroxyquinolin-2(1H)- one are among the more potent inhibitors of H1N1 influenza A endonuclease. An X-ray crystal structure of 7-(p-fluorophenyl)-3-hydroxyquinolin-2(1H)-one complexed to the influenza endonuclease revealed that this molecule chelates to two metal ions at the active site of the enzyme.
Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinolin-2(1H)-one series of potent D-amino acid oxidase (DAAO) inhibitors
Duplantier, Allen J.,Becker, Stacey L.,Bohanon, Michael J.,Borzilleri, Kris A.,Chrunyk, Boris A.,Downs, James T.,Hu, Lain-Yen,El-Kattan, Ayman,James, Larry C.,Liu, Shenping,Lu, Jiemin,Maklad, Noha,Mansour, Mahmoud N.,Mente, Scot,Piotrowski, Mary A.,Sakya, Subas M.,Sheehan, Susan,Steyn, Stefanus J.,Strick, Christine A.,Williams, Victoria A.,Zhang, Lei
experimental part, p. 3576 - 3585 (2010/03/30)
3-Hydroxyquinolin-2(1H)-one (2) was discovered by high throughput screening in a functional assay to be a potent inhibitor of human DAAO, and its binding affinity was confirmed in a Biacore assay. Cocrystallization of 2 with the human DAAO enzyme defined
