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.
A Visible-Light Promoted Amine Oxidation Catalyzed by a Cp*Ir Complex
Davis, Holly Jane,H?ussinger, Daniel,Ward, Thomas R.,Okamoto, Yasunori
, p. 4512 - 4516 (2020/07/27)
Through a rapid screening of Cp*Ir complexes based on a turn-on type fluorescence readout, a [Cp*Ir(dipyrido[3,2-a : 2’,3’-c]phenazine)Cl]+ complex was found to catalyze the blue-light promoted dehydrogenation of N-heterocycles under physiological conditions. In the dehydrogenation of tetrahydroisoquinolines, the catalyst preferentially yielded the monodehydrogenated product, accompanying H2O2 generation. We surmise that this mechanism may be reminiscent of flavin-dependent oxidases.
