1721-93-3Relevant articles and documents
Enantioselective addition of organolithium reagents on isoquinoline
Alexakis, Alexandre,Amiot, Franck
, p. 2117 - 2122 (2002)
1-Methyl-1,2-dihydroisoquinoline and 1-butyl-1,2-dihydroisoquinoline were obtained by enantioselective addition of organolithium reagents on the isoquinoline. (-)-Sparteine was used as an external catalytic chiral ligand and an enantiomeric excess of 57%
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Nozaki et al.
, p. 1123 (1966)
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Isoquinoline thiosemicarbazone displays potent anticancer activity with: In vivo efficacy against aggressive leukemias
Sun, Daniel L.,Poddar, Soumya,Sun, Daniel L.,Pan, Roy D.,Poddar, Soumya,Rosser, Ethan W.,Pan, Roy D.,Abt, Evan R.,Rosser, Ethan W.,Van Valkenburgh, Juno,Abt, Evan R.,Le, Thuc M.,Van Valkenburgh, Juno,Lok, Vincent,Le, Thuc M.,Song, Janet,Li, Joanna,Hernandez, Selena P.,Mona, Christine E.,Stuparu, Andreea D.,Czernin, Johannes,Turlik, Aneta,Donahue, Timothy R.,Chen, Xiaohong,Radu, Caius G.,Cheng, Chi-An,Hernandez, Selena P.,Chen, Wei,Mona, Christine E.,Stuparu, Andreea D.,Vergnes, Laurent,Reue, Karen,Damoiseaux, Robert,Zink, Jeffrey I.,Czernin, Johannes,Donahue, Timothy R.,Houk, Kendall N.,Jung, Michael E.,Radu, Caius G.
, p. 392 - 410 (2020)
A potent class of isoquinoline-based Α-N-heterocyclic carboxaldehyde thiosemicarbazone (HCT) compounds has been rediscovered; based upon this scaffold, three series of antiproliferative agents were synthesized through iterative rounds of methylation and fluorination modifications, with anticancer activities being potentiated by physiologically relevant levels of copper. The lead compound, HCT-13, was highly potent against a panel of pancreatic, small cell lung carcinoma, prostate cancer, and leukemia models, with IC50 values in the low-to-mid nanomolar range. Density functional theory (DFT) calculations showed that fluorination at the 6-position of HCT-13 was beneficial for ligand-copper complex formation, stability, and ease of metal-center reduction. Through a chemical genomics screen, we identify DNA damage response/replication stress response (DDR/RSR) pathways, specifically those mediated by ataxia-telangiectasia and Rad3-related protein kinase (ATR), as potential compensatory mechanism(s) of action following HCT-13 treatment. We further show that the cytotoxicity of HCT-13 is copper-dependent, that it promotes mitochondrial electron transport chain (mtETC) dysfunction, induces production of reactive oxygen species (ROS), and selectively depletes guanosine nucleotide pools. Lastly, we identify metabolic hallmarks for therapeutic target stratification and demonstrate the in vivo efficacy of HCT-13 against aggressive models of acute leukemias in mice.
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Barrows,Lindwall
, p. 2430 (1942)
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Synthesis of novel functionalized 5-nitroisoquinolines and evaluation of in vitro antimalarial activity
Rathelot,Vanelle,Gasquet,Delmas,Crozet,Timon-David,Maldonado
, p. 503 - 508 (1995)
Novel aldimine and hydrazone isoquinoline derivatives were obtained after subjecting 1-formyl-5-nitroisoquinoline to classical reactions. Some of these compounds were found to have activity against a chloroquine-resistant Plasmodium falciparum strain (ACC Niger).
1,4-Dehydrochlorination of 1-(1-haloalkyl)-3,4-dihydroisoquinolines as a convenient route to functionalized isoquinolines
Jacobs, Jan,Van, Tuyen Nguyen,Stevens, Christian V.,Markusse, Peter,De Cooman, Paul,Maat, Leendert,De Kimpe, Norbert
, p. 3698 - 3701 (2009)
1-Chloroalkyl-, 1-(2,2-dichloroalkyl)-, and 1-(trichloromethyl)-3,4-dihydroisoquinolines are synthesized by chlorination of 1-alkyl-3,4-dihydroisoquinolines with N-chlorosuccinimide. These novel chlorinated 3,4-dihydroisoquinolines are suitable precursors for functionalized isoquinolines by aromatization involving sequential 1,4-dehydrochlorination, tautomerization, and nucleophilic substitution.
A ortho position alkylation method of organic compound containg pyridine
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Paragraph 0108-0116, (2020/12/05)
A process for introducing alkyl at ortho positions of organic compounds containing pyridine. The method is not affected by the kind of substituent bonded to the pyridine and can be alkylated with high positional selectivity and high yield at N-based ortho-position of pyridine without being affected by the kind of substituent introduced to pyridine ortho position (pyridine N-based) can be advantageously used for the preparation of a compound containing an alkyl-introduced pyridine structure.
Rh/TiO2-Photocatalyzed Acceptorless Dehydrogenation of N-Heterocycles upon Visible-Light Illumination
Bahnemann, Detlef W.,Balayeva, Narmina O.,Dillert, Ralf,Mamiyev, Zamin,Zheng, Nan
, p. 5542 - 5553 (2020/08/25)
TiO2 is an effective and extensively employed photocatalyst, but its practical use in visible-light-mediated organic synthesis is mainly hindered by its wide band gap energy. Herein, we have discovered that Rh-photodeposited TiO2 nanoparticles selectively dehydrogenate N-heterocyclic amines with the concomitant generation of molecular hydrogen gas in an inert atmosphere under visible light (λmax = 453 nm) illumination at room temperature. Initially, a visible-light-sensitive surface complex is formed between the N-heterocycle and TiO2. The acceptorless dehydrogenation of N-heterocycles is initiated by direct electron transfer from the HOMO energy level of the amine via the conduction band of TiO2 to the Rh nanoparticle. The reaction condition was optimized by examining different photodeposited noble metals on the surface of TiO2 and solvents, finding that Rh0 is the most efficient cocatalyst, and 2-propanol is the optimal solvent. Structurally diverse N-heterocycles such as tetrahydroquinolines, tetrahydroisoquinolines, indolines, and others bearing electron-deficient as well as electron-rich substituents underwent the dehydrogenation in good to excellent yields. The amount of released hydrogen gas evinces that only the N-heterocyclic amines are oxidized rather than the dispersant. This developed method demonstrates how UV-active TiO2 can be employed in visible-light-induced synthetic dehydrogenation of amines and simultaneous hydrogen storage applications.
