10342-85-5Relevant articles and documents
Asymmetric Reduction of Electron-Rich Ketones with Tethered Ru(II)/TsDPEN Catalysts Using Formic Acid/Triethylamine or Aqueous Sodium Formate
Soni, Rina,Hall, Thomas H.,Mitchell, Benjamin P.,Owen, Matthew R.,Wills, Martin
, p. 6784 - 6793 (2015)
The asymmetric transfer hydrogenation (ATH) of ketones under aqueous conditions using tethered Ru(II)/6-arene/diamine catalysts is described, as is the ATH of electron-rich substrates containing amine and methoxy groups on the aromatic rings. Although such substrates are traditionally challenging ones for ATH, the tethered catalysts work very efficiently. In the case of amino-substituted ketones, aqueous conditions give excellent results; however, for methoxy-substituted substrates, the more established formic acid/triethylamine system gives superior results.
High-Throughput Experimentation and Continuous Flow Evaluation of Nucleophilic Aromatic Substitution Reactions
Aremu, Deborah,Avramova, Larisa,Cooks, R. Graham,Jaman, Zinia,Logsdon, David L.,Sobreira, Tiago J. P.,Szilágyi, Botond,Thompson, David H.
, (2020)
Nucleophilic aromatic substitution (SNAr) reactions were optimized using high-throughput experimentation techniques for execution under flow conditions. A total of 3072 unique reactions were evaluated with an analysis time of ～3.5 s per reaction using a system that combines a liquid handling robot for reaction mixture preparation with desorption electrospray ionization (DESI) mass spectrometry (MS) for analysis. The reactions were performed in bulk microtiter arrays with and without incubation. In-house developed software was used to process the data and generate heat maps of the results. This information was then used to select the most promising conditions for continuous synthesis under microfluidic reactor conditions. Our results show that this HTE approach provides robust guidance for narrowing the range of conditions needed for optimization of SNAr reactions.
Palladium-catalyzed selective amination of haloaromatics on KF-alumina surface
Basu, Basudeb,Das, Pralay,Nanda, Ashish K.,Das, Sajal,Sarkar, Sajal
, p. 1275 - 1278 (2005)
An efficient palladium-catalyzed amination, including polyaminations of aromatic bromides mediated on a surface of KF-alumina, is reported. The solvent-free one-pot protocol avoids the use of a strong base (sodium tert-butoxide) making it applicable to substrates containing a base-sensitive functional group. It proceeds without concomitant reductive bromination and provides access to selective amination of polyhaloaromatics.
A novel and unusual method for C[sbnd]N bond formation between benzene ring and various amines
Wang, Peng,Wang, Chen,Zhu, Zhenzhen,Xu, Sicong,Hou, Yunlei,Zhao, Yanfang
, (2021/09/09)
A new approach to form C[sbnd]N bond without metal catalysis was developed. 4-acetylbenzoyl isocyanate reacted with various amines through a mild method to form C[sbnd]N bond. This reaction was amenable to scale-up and it afforded the corresponding products with good to excellent yields and tolerates a wide range of functional groups.
Design, Synthesis and Antitubercular Activity of Novel Isoniazid?Cyclic?Amine?Azachalcones Hybrids
Barbosa, Sandro L.,Baroni, Adriano C. M.,Croda, Júlio,Gomes, Giovana B.,Guerrero, Palimécio G.,Moreira, Flora M. F.,Oliveira, Jefferson R. S.,Perdomo, Renata T.,Shiguemoto, Cristiane Y. K.,das Neves, Amarith R.
, p. 1284 - 1295 (2020/10/14)
In this work, it is described the design of twenty-four heterocyclic amine-azachalcones compounds through molecular hybridization of chalcone scaffold and fragments of isoniazid, fluoroquinolones, and linezolid with antituberculosis potential. The new compounds were synthesized via Claisen-Schmidt condensation, providing yields of 36-95%. Fifteen compounds showed antituberculosis activity against Mycobacterium tuberculosis H37Rv strain. Two amine-azachalcones 15 and 17 showed relevant biological activity with minimum inhibitory concentration (MIC) values of 6.62 and 4.85 μM, respectively. Compound 12 showed the best profile of antitubercular activity with MIC = 9.54 μM and selectivity index (SI) = 9.33. It was found that morpholine group is important to increase potency of antimycobacterial activity but also to add some toxicity to the chalcone molecular framework. The results described herein would be a guide in the designing of novel and optimized antitubercular derivatives based on the chalcone scaffold.
General Paradigm in Photoredox Nickel-Catalyzed Cross-Coupling Allows for Light-Free Access to Reactivity
Nocera, Daniel G.,Qin, Yangzhong,Sun, Rui
supporting information, p. 9527 - 9533 (2020/04/08)
Self-sustained NiI/III cycles are established as a potentially general paradigm in photoredox Ni-catalyzed carbon–heteroatom cross-coupling reactions through a strategy that allows us to recapitulate photoredox-like reactivity in the absence of light across a wide range of substrates in the amination, etherification, and esterification of aryl bromides, the latter of which has remained, hitherto, elusive under thermal Ni catalysis. Moreover, the accessibility of esterification in the absence of light is especially notable because previous mechanistic studies on this transformation under photoredox conditions have unanimously invoked energy-transfer-mediated pathways.
COMPOUNDS AND METHODS OF THEIR USE
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Page/Page column 85, (2020/05/19)
Provided are agents capable of binding the KIX domain of CBP or MED15 to inhibit the binding between SREBP1 and the KIX domain of MED15 or CBP. Also provided are compositions containing the agents and methods of their use.
Piperidine ring containing chalcone compound as well as preparation and application of piperidine ring containing chalcone compound
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Paragraph 0009; 0018-0021, (2019/07/04)
The invention provides a piperidine ring containing chalcone compound. The piperidine ring containing chalcone compound is prepared by mixing fluoroacetophenone and piperidine, heating, refluxing, then mixing with an aromatic aldehyde compound, and heating and refluxing to react in a solvent under the alkaline action. The preparation condition is mild, the operation is convenient, the cost is low,and the industrial application prospect is broad. The provided piperidine ring containing chalcone compound shows better anti-breast cancer activity, lays a foundation for the screening and developing of new drugs, has an important practical value, and can be applied to preparing drugs for treating breast cancer; the structural general formula is shown in the description.
Application of hydrazino and hydrazido linkers to connect benzenesulfonamides with hydrophilic/phobic tails for targeting the middle region of human carbonic anhydrases active site: Selective inhibitors of hCA IX
Allam, Heba Abdelrasheed,Fahim, Samar H.,F.Abo-Ashour, Mahmoud,Nocentini, Alessio,Elbakry, Mohamed E.,Abdelrahman, Mohamed A.,Eldehna, Wagdy M.,Ibrahim, Hany S.,Supuran, Claudiu T.
, p. 547 - 556 (2019/07/04)
Herein we report the design and synthesis of three different sets of novel benzenesulfonamides (5a-e, 7a-e and 10a-d) incorporating hydrophilic/hydrophobic tails by hydrazido or hydrazino linkers. The newly synthesized benzenesulfonamides were examined in vitro for their inhibitory activity towards four human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII using a stopped-flow CO2 hydrase assay. All these isoforms were inhibited by the sulfonamides (5a-e, 7a-e and 10a-d) with variable degrees in the following KI ranges: 76.8–357.4 nM for hCA I, 8.2–94.6 nM for hCA II, 2.0–46.3 nM for hCA XI, and 8.3–88.3 nM for hCA XII. The sulfonamide 7d exhibited potent anti-proliferative activity against breast MCF-7 cancer cell line under both normoxic and hypoxic conditions with IC50 values equal 3.32 ± 0.06 and 8.53 ± 0.32 μM, respectively, which are comparable to the reference drug doxorubicin (IC50 = 2.36 ± 0.04 and 8.39 ± 0.25 μM, respectively). Furthermore, 7d was screened for cell cycle disturbance and apoptosis induction in MCF-7 cells. It was found to persuade cell cycle arrest at G2-M stage as well as to alter the Sub-G1 phase, also, 7d resulted in a significant increase in the percent of annexinV-FITC positive apoptotic cells from 1.03 to 18.54%. Molecular docking study was carried out for 7d within the hCA IX and hCA XII active sites to rationalize the obtained inhibition results.
A group of diphosphine-thiosemicarbazone complexes of palladium: Efficient precursors for catalytic C–C and C–N coupling reactions
Thapa, Kiran,Paul, Piyali,Bhattacharya, Samaresh
, p. 232 - 239 (2018/11/06)
Reaction of 4-R-benzaldehyde thiosemicarbazone (denoted in general as HL-R; where H stands for the dissociable acidic proton and R (R = OCH3, CH3, H, Cl and NO2) for the substituent) with [Pd(dppe)(EtOH)2]2+, generated in situ via interaction of [Pd(dppe)Cl2] (dppe = 1,2-bis(diphenylphosphino)ethane) with AgNO3 in hot ethanol, in the presence of triethylamine affords a group of orange complexes of the type [Pd(dppe)(L-R)]NO3. Structures of [Pd(dppe)Cl2] and [Pd(dppe)(L-OCH3)]NO3 have been determined by X-ray crystallography. In the [Pd(dppe)(L-R)]NO3 complexes, the thiosemicarbazone ligands are coordinated to the metal center as monoanionic bidentate N,S-donors forming five-membered chelate rings. The [Pd(dppe)(L-R)]NO3 complexes show intense absorptions in the visible and ultraviolet regions, which have been analyzed by TDDFT calculations. All the [Pd(dppe)(L-R)]NO3 complexes are found to efficiently catalyze Suzuki-type C–C and Buchwald-type C–N coupling reactions.
