14547-73-0Relevant articles and documents
Bis-picolinamide Ruthenium(III) Dihalide Complexes: Dichloride-to-Diiodide Exchange Generates Single trans Isomers with High Potency and Cancer Cell Selectivity
Basri, Aida M.,Lord, Rianne M.,Allison, Simon J.,Rodríguez-Bárzano, Andrea,Lucas, Stephanie J.,Janeway, Felix D.,Shepherd, Helena J.,Pask, Christopher M.,Phillips, Roger M.,McGowan, Patrick C.
, p. 6341 - 6356 (2017)
A library of new bis-picolinamide ruthenium(III) dihalide complexes of the type [RuX2L2] (X=Cl or I, L=picolinamide) have been synthesised and characterised. The complexes exhibit different picolinamide ligand binding modes, whereby one ligand is bound (N,N) and the other bound (N,O). Structural studies revealed a mixture of cis and trans isomers for the [RuCl2L2] complexes but upon a halide exchange reaction to yield [RuI2L2], only single trans isomers were detected. High cytotoxic activity against human cancer cell lines was observed, with the potencies of some complexes similar to or better than cisplatin. The conversion to [RuI2L2] substantially increased the activity towards cancer cell lines by more than twelvefold. The [RuI2L2] complexes displayed potent activity against the A2780cis (cisplatin-resistant human ovarian cancer) cell line, with a more than fourfold higher potency than cisplatin. Equitoxic activity was observed against normoxic and hypoxic cancer cells, which indicates the potential to eradicate both the hypoxic and aerobic fractions of solid tumours with similar efficiency. The activity of selected complexes against non-cancer ARPE-19 cells was also tested. The [RuI2L2] complexes were found to be more potent than the [RuCl2L2] analogues and also more selective towards cancer cells with a selectivity factor in excess of sevenfold.
Copper-mediated ortho C–H primary amination of anilines
Cheng, Tai-Jin,Wang, Xing,Xu, Hui,Dai, Hui-Xiong
supporting information, (2021/05/10)
We report herein a copper-mediated ortho C–H primary amination of anilines by using cheap and commercially available benzophenone imine as the amination reagent. The protocol show good functional group tolerance and heterocyclic compatibility. Late-stage diversification of drugs demonstrate the synthetic utility of this protocol.
A metal-free picolinamide assisted electrochemical ortho-trifluoromethylation of arylamines
Wang, Kai,Hou, Jiahao,Wei, Tingting,Zhang, Changjun,Bai, Renren,Xie, Yuanyuan
supporting information, (2020/12/21)
An eco-friendly and effective electrochemical process was developed for the ortho-trifluoromethylation of arylamines using CF3SO2Na as the trifluoromethyl source, affording the desired products in moderate to good yields with high regioselectivity under mild reaction conditions. Importantly, the requirement for both transition metals and oxidants utilized in previous methods were avoided. A radical mechanism was proposed on the basis of various control experiments.
Copper(ii) mediatedorthoC-H alkoxylation of aromatic amines using organic peroxides: efficient synthesis of hindered ethers
Sarkar, Souvik,Sahoo, Tapan,Sen, Chiranjit,Ghosh, Subhash Chandra
supporting information, p. 8949 - 8952 (2021/09/10)
Synthesis of hindered alkyl aryl ether derivatives (R-O-Ar) remains a huge challenge and highly desirable in organic and medicinal chemistry because extensive substitution on the ether bond prevents the undesired metabolic process and thus avoids rapid de
Method for selectively synthesizing halogenated arylamine through copper catalysis (by machine translation)
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Paragraph 0079-0082, (2020/12/30)
The method comprises the following steps: reacting a substrate with a halogenating reagent (III) in an organic solvent to obtain a catalyst. The reaction 0 - 80 °C is reacted at 0.5 - 6h under the action of an oxidizing agent, and after the reaction is finished, the reaction liquid is subjected to post-treatment to obtain the product halogenated aromatic amine compound. To the invention, direct synthesis of the halogenated aromatic amine compounds is achieved for the first time, and the problems that in the traditional method, the metal catalyst is expensive, the halogenated reagent toxicity is large, byproducts are large and the like are solved. At the same time, the product can take off the pyridine guide group through simple hydrolysis, and further functional groups can be combined into an aromatic heterocyclic compound. The method is simple and convenient to operate, mild in reaction conditions, high in selectivity, high in product yield and wide in substrate applicability, and is an efficient organic synthesis means. : Substrate: Halogenating agent: Product: (by machine translation)
Reversible small molecule inhibitors of MAO A and MAO B with anilide motifs
Grau, Kathrin,Hagenow, Jens,Hagenow, Stefanie,Hefke, Lena,Khanfar, Mohammad,Proschak, Ewgenij,Stark, Holger
, p. 371 - 393 (2020/02/11)
Background: Ligands consisting of two aryl moieties connected via a short spacer were shown to be potent inhibitors of monoamine oxidases (MAO) A and B, which are known as suitable targets in treatment of neurological diseases. Based on this general blueprint, we synthesized a series of 66 small aromatic amide derivatives as novel MAO A/B inhibitors. Methods: The compounds were synthesized, purified and structurally confirmed by spectroscopic methods. Fluorimetric enzymological assays were performed to determine MAO A/B inhibition properties. Mode and reversibility of inhibition was determined for the most potent MAO B inhibitor. Docking poses and pharmacophore models were generated to confirm the in vitro results. Results: N-(2,4-Dinitrophenyl)benzo[d][1,3]dioxole-5-carboxamide (55, ST-2043) was found to be a reversible competitive moderately selective MAO B inhibitor (IC50 = 56 nM, Ki = 6.3 nM), while N-(2,4-dinitrophenyl)benzamide (7, ST-2023) showed higher preference for MAO A (IC50 = 126 nM). Computational analysis confirmed in vitro binding properties, where the anilides examined possessed high surface complementarity to MAO A/B active sites. Conclusion: The small molecule anilides with different substitution patterns were identified as potent MAO A/B inhibitors, which were active in nanomolar concentrations ranges. These small and easily accessible molecules are promising motifs, especially for newly designed multitargeted ligands taking advantage of these fragments.
Copper-Catalyzed Electrophilic Ortho C(sp2)-H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System
Begam, Hasina Mamataj,Choudhury, Rajarshee,Behera, Ashok,Jana, Ranjan
supporting information, p. 4651 - 4656 (2019/06/17)
A practical copper-catalyzed, 2-picolinamide-directed ortho C-H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, b
Rh-Catalyzed Annulative Insertion of Terminal Olefin onto Pyridines via a C-H Activation Strategy Using Ethenesulfonyl Fluoride as Ethylene Provider
Li, Chen,Qin, Hua-Li
supporting information, p. 4495 - 4499 (2019/06/27)
A Rh(III)-catalyzed annulative insertion of ethylene onto picolinamides was achieved, providing a portal to a class of unique pyridine-containing molecules bearing a terminal olefin moiety for diversification. Application of this method for modification of Sorafenib was also accomplished.
IMIDAZOPYRIDINAMINE PHENYL DERIVATIVE AND USE THEREOF
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Paragraph 0038, (2019/05/16)
The present invention relates to imidazopyridinamine phenyl derivatives, pharmaceutically acceptable salts and hydrates thereof, or metabolites thereof formed by any form of metabolism, and uses thereof in the preparation of medicaments for preventing and
Copper-Catalyzed Electrochemical C-H Amination of Arenes with Secondary Amines
Yang, Qi-Liang,Wang, Xiang-Yang,Lu, Jia-Yan,Zhang, Li-Pu,Fang, Ping,Mei, Tian-Sheng
, p. 11487 - 11494 (2018/09/13)
Electrochemical oxidation represents an environmentally friendly solution to conventional methods that require caustic stoichiometric chemical oxidants. However, C-H functionalizations merging transition-metal catalysis and electrochemical techniques are, to date, largely confined to the use of precious metals and divided cells. Herein, we report the first examples of copper-catalyzed electrochemical C-H aminations of arenes at room temperature using undivided electrochemical cells, thereby providing a practical solution for the construction of arylamines. The use of n-Bu4NI as a redox mediator is crucial for this transformation. On the basis of mechanistic studies including kinetic profiles, isotope effects, cyclic voltammetric analyses, and radical inhibition experiments, the reaction appears to proceed via a single-electron-transfer (SET) process, and a high valent Cu(III) species is likely involved. These findings provide a new avenue for transition-metal-catalyzed electrochemical C-H functionalization reactions using redox mediators.
