4494-18-2Relevant academic research and scientific papers
Isoquinoline in the synthesis of 1-dichloromethylisoquinoline and 1-formylisoquinoline
Khusnutdinov,Baiguzina,Mukminov
, p. 706 - 708 (2010)
By the reaction of isoquinoline with CCl4 and methanol catalyzed by iron-containing compounds a synthesis was performed of 1- dichloromethylisoquinoline that was quantitatively converted into 1-formylisoquinoline by the treatment with dimethyl sulfoxide. Pleiades Publishing, Ltd., 2010.
Catalytic Approach toward Chiral P,N-Chelate Complexes Utilizing the Asymmetric Hydrophosphination Protocol
Katona, Dávid,Leung, Pak-Hing,Li, Yongxin,Lu, Yunpeng,Pullarkat, Sumod A.
, (2020)
A synthetic procedure for obtaining a chiral P,N ligand was developed by exploiting the versatility of the asymmetric hydrophosphination protocol catalyzed by a phosphapalladacycle complex. The addition of the synthesized ligand to various metal sources led to the generation of chiral and enantioenriched chelate complexes, which can be useful prototypes for catalyst design in the future. The resulting coordination compounds were comprehensively characterized by solid-state (X-ray crystallography) and solution-based (one- and two-dimensional NMR spectroscopy) techniques and natural bond orbital (density functional theory) analysis to determine their structural and key electronic features.
Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes
Xu, Jincheng,Li, Yang,Ding, Tianling,Guo, Hao
supporting information, p. 3114 - 3117 (2021/09/03)
A convenient protocol for the synthesis of quinoline-4-carbaldehydes via chemoselective oxidation of 4-methylquinolines using hypervalent iodine(III) reagents as oxidant is described. This method highlights metal-free and mild reaction conditions, nice yield, good functional group tolerance, and high chemoselectivity.
Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines
Wu, Yue,Guo, Peng,Chen, Long,Duan, Weijie,Yang, Zengzhuan,Wang, Tao,Chen, Ting,Xiong, Fei
supporting information, p. 3271 - 3274 (2021/04/07)
The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.
NNYTHIOSEMICARBAZONE COMPOUNDS AND USES THEREOF
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Paragraph 0407-0409, (2020/09/12)
Provided, inter alia, are thiosemicarbazone compounds, metal complexes of thi osemi carb azone compounds, pharmaceutical compositions, and methods for treating cancer.
Preparation method of formaldehyde-substituted aza-condensed ring compound
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Paragraph 0141-0142; 0145-0147, (2020/06/02)
The invention provides a preparation method of a formaldehyde-substituted aza-condensed ring compound, comprising the following steps: by using an aza-condensed ring lactam compound as a starting material, carrying out halogenation reaction, methylation reaction and methyl oxidation reaction to obtain the formaldehyde-substituted aza-condensed ring compound. According to the preparation method ofthe formaldehyde-substituted aza-condensed ring compound, the whole synthesis route is good in step repeatability, mild in operation condition and high in safety, and large-scale production and industrial popularization are facilitated; post-treatment energy consumption is low, a large amount of toxic wastewater is not generated, no pollution is caused to the environment, the production safety level and the production cost are reduced, application of green and environment-friendly industrial production is facilitated, and wide application prospects are achieved.
SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX
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Paragraph 00152, (2020/12/29)
Compositions and methods for treating thrombosis, inflammation, and atherosclerosis by administration of a compound that binds to KRIT1 to inhibit binding with HEG1.
PARG INHIBITORS AND METHOD OF USE THEREOF
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Paragraph 0601; 0607; 0608, (2020/02/16)
Provided herein are, inter alia, methods of treating cancer using compounds of the invention.
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 (2020/04/15)
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.
Photoredox-Catalyzed Redox-Neutral Minisci C?H Formylation of N-Heteroarenes
Dong, Jianyang,Wang, Xiaochen,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 2155 - 2159 (2020/02/11)
We report a protocol for redox-neutral Minisci C?H formylation of N-heteroarenes using 1,3-dioxoisoindolin-2-yl 2,2-diethoxyacetate as a formyl equivalent at room temperature. This scalable benchtop protocol offers a distinct advantage over traditional reductive carbonylation and Minisci C?H formylation methods in not requiring the use of carbon monoxide, pressurized gas, a stoichiometric reductant, or a stoichiometric oxidant. (Figure presented.).
