26386-86-7Relevant articles and documents
2,2'-Biindolyl revisited. Synthesis and reactions
Bergman,Koch,Pelcman
, p. 5631 - 5642 (1995)
An improved synthesis of 2,2'-biindolyl (1) is described. Derivatives of 1 with a variety of substituents in the 3,3'-positions, such as the 3,3'-diformyl derivative 19 have been synthesized. Potential syntheses of indolocarbazole alkaloids from such deri
Engineering Boron Hot Spots for the Site-Selective Installation of Iminoboronates on Peptide Chains
Russo, Roberto,Padanha, Rita,Fernandes, Fábio,Veiros, Luis F.,Corzana, Francisco,Gois, Pedro M. P.
supporting information, p. 15226 - 15231 (2020/10/20)
Boronic acids (BAs) are a promising bioconjugation function to design dynamic materials as they can establish reversible covalent bonds with oxygen/nitrogen nucleophiles that respond to different pH, ROS, carbohydrates and glutathione levels. However, the dynamic nature of these bonds also limits the control over the stability and site-selectivity of the bioconjugation, which ultimately leads to heterogeneous conjugates with poor stability under physiological conditions. Here we disclose a new strategy to install BAs on peptide chains. In this study, a “boron hot spot“ based on the 3-hydroxyquinolin-2(1H)-one scaffold was developed and upon installation on a peptide N-terminal cysteine, enables the site-selective formation of iminoboronates with 2-formyl-phenyl boronic acids (Ka of 58128±2 m?1). The reaction is selective in the presence of competing lysine ?-amino groups, and the resulting iminoboronates, displayed improved stability in buffers solutions and a cleavable profile in the presence of glutathione. Once developed, the methodology was used to prepare cleavable fluorescent conjugates with a laminin fragment, which enabled the validation of the 67LR receptor as a target to deliver cargo to cancer HT29 cells.
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.
, 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.
Enantioselective Excited-State Photoreactions Controlled by a Chiral Hydrogen-Bonding Iridium Sensitizer
Skubi, Kazimer L.,Kidd, Jesse B.,Jung, Hoimin,Guzei, Ilia A.,Baik, Mu-Hyun,Yoon, Tehshik P.
, p. 17186 - 17192 (2017/12/06)
Stereochemical control of electronically excited states is a long-standing challenge in photochemical synthesis, and few catalytic systems that produce high enantioselectivities in triplet-state photoreactions are known. We report herein an exceptionally effective chiral photocatalyst that recruits prochiral quinolones using a series of hydrogen-bonding and π-π interactions. The organization of these substrates within the chiral environment of the transition-metal photosensitizer leads to efficient Dexter energy transfer and effective stereoinduction. The relative insensitivity of these organometallic chromophores toward ligand modification enables the optimization of this catalyst structure for high enantiomeric excess at catalyst loadings as much as 100-fold lower than the optimal conditions reported for analogous chiral organic photosensitizers.
Enantioselective, intermolecular [2+2] photocycloaddition reactions of 3-acetoxyquinolone: Total synthesis of (-)-pinolinone
Mayr, Florian,Wiegand, Christian,Bach, Thorsten
, p. 3353 - 3355 (2014/03/21)
The natural product (-)-pinolinone was synthesised via a concise route (six steps, 17% overall yield) from 3-acetoxyquinolone, employing an enantioselective intermolecular [2+2] photocycloaddition as the key step. The Royal Society of Chemistry 2014.
THERAPEUTIC HYDROXYQUINOLONES
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Page/Page column 34, (2014/05/24)
The invention provides compounds of formula (I) and salts thereof wherein R4-R8 have any of the meanings defined in the specification, as well as pharmaceutical compositions comprising the compounds or salts and methods for their use in therapy. The compounds have useful antiviral properties.
Pinacol rearrangement of 3,4-dihydro-3,4-dihydroxyquinolin-2(1H)-ones: An alternative pathway to viridicatin alkaloids and their analogs
Rudolf, Ondrej,Rouchal, Michal,Lycka, Antonin,Klasek, Antonin
, p. 1905 - 1917 (2013/11/06)
3-Alkyl/aryl-3-hydroxyquinoline-2,4-diones were reduced with NaBH 4 to give cis-3-alkyl/aryl-3,4-dihydro-3,4-dihydroxyquinolin-2(1H)- ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SOs
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.
Ring-expansion reaction of isatins with ethyl diazoacetate catalyzed by dirhodium(II)/DBU metal-organic system: En route to viridicatin alkaloids
Paterna, Roberta,Andre, Vania,Duarte, M. Teresa,Veiros, Luis F.,Candeias, Nuno R.,Gois, Pedro M. P.
, p. 6280 - 6290 (2013/10/21)
We present here the NHC-dirhodium(II)/DBU-catalyzed ring expansion reaction of isatins with ethyl diazoacetate. This new one-pot protocol yields the ethyl 3-hydroxy-2(1H)-oxoquinoline-4-carboxylate core, regioselectively and in good to excellent yields. A DFT mechanistic study indicates metallocarbene formation between the 3-hydroxyindole-diazo intermediate and the dirhodium(II) complex to be the rate-limiting step of the reaction. The synthesized ethyl 3-hydroxy-2(1H)-oxoquinoline-4-carboxylate core could be readily converted to viridicatin alkaloids, in yields up to 80 % by a microwave-assisted Suzuki-Miyaura cross coupling of the 3-hydroxy-4-bromoquinolin-2(1H)-one with arylboronic acid. Copyright
Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity
Suchaud, Virginie,Bailly, Fabrice,Lion, Cedric,Tramontano, Enzo,Esposito, Francesca,Corona, Angela,Christ, Frauke,Debyser, Zeger,Cotelle, Philippe
, p. 3988 - 3992 (2012/07/03)
We report herein the synthesis of a series of 3-hydroxyquinolin-2(1H)-one derivatives. Esters and amide groups were introduced at position 4 of the basis scaffold and some modulations of the benzenic moiety were performed. Most compounds presented selecti
