3334-89-2Relevant academic research and scientific papers
Tropylium derivatives as new entrants that sense quadruplex structures
Hori, Daisuke,Park, Soyoung,Sugiyama, Hiroshi,Yum, Ji Hye
supporting information, p. 1948 - 1953 (2021/09/10)
G-quadruplex (G4) is the most well-known noncanonical conformation of DNA involved in diverse pharmacological and biological contexts. G4 ligands have been actively developed as molecular probes and tumor therapeutic reagent candidates. They have also been used to detect the presence of G4s and identify their biological roles. Currently used ligands are commonly aromatic, planar, and electron deficient for effective interaction with G4s. Recognizing that tropylium cations possess the aforementioned features of effective G4 ligands, we prepared tropylium derivatives to validate their binding affinity with G4s. Titration against various DNA sequences revealed gradual changes in the UVvis spectra of the tropylium derivatives. A strong hypochromic effect, indicating intercalation or ππ stacking, was observed when c-kit DNA was present in a binding ratio of 2:1 (ligand:DNA). The energetically minimized binding model showed that the G4ligand complexes were stabilized by electrostatic interactions. Encouraged by the present findings, the application of tropylium derivatives in cellular contexts is underway.
Synthesis of 2-Arylisoindoline Derivatives Catalyzed by Reusable 1,2,4-Triazole Iridium on Mesoporous Silica through a Cascade Borrowing Hydrogen Strategy
Yao, Wei,Ge, Chenyang,Zhang, Yilin,Xia, Xiao-Feng,Wang, Long,Wang, Dawei
supporting information, p. 16099 - 16105 (2019/11/26)
Covalent attachment of a 1,2,4-triazole iridium complex to mesoporous MCM-41 generated a heterogeneous catalyst that was found to be effective in the synthesis of 2-aryl isoindolines, quinolines, cyclic amines, and symmetrical secondary amines through a cascade borrowing hydrogen strategy. Interestingly, the supported heterogeneous iridium catalyst prepared from the 1,2,4-triazole iridium complex and mesoporous MCM-41 exhibited high catalytic activity in the preparation of 2-aryl isoindoline derivatives and symmetrical secondary amines. The catalyst system is highly recyclable for at least five times. Besides the important effect of the triazole, iridium sites grafted on siliceous supports can act as multifunctional catalytic centers and thus greatly enhance the catalytic activity of the catalysts. Furthermore, mechanistic experiments revealed that the reaction is initiated by an initial alcohol dehydrogenation and promoted by an iridium hydride intermediate. Importantly, the direct detection of a diagnostic iridium hydride signal confirmed that the synthesis of 2-aryl isoindolines occurs by a borrowing hydrogen process. This work provides an efficient example of isoindolines synthesis through a borrowing hydrogen strategy.
Practical and regioselective amination of arenes using alkyl amines
Ruffoni, Alessandro,Juliá, Fabio,Svejstrup, Thomas D.,McMillan, Alastair J.,Douglas, James J.,Leonori, Daniele
, p. 426 - 433 (2019/05/01)
The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.
n-Butyllithium-mediated synthesis of N-aryl tertiary amines by reactions of fluoroarenes with secondary amines at room temperature
Lin, Yingyin,Li, Meng,Ji, Xinfei,Wu, Jingjing,Cao, Song
, p. 1466 - 1472 (2017/02/18)
A simple and facile method for the synthesis of aromatic tertiary amines by amination of fluoroarenes with secondary amines in the presence of n-butyllithium at room temperature was reported.
GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES
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Paragraph 0001296, (2015/04/15)
Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).
N-heterocyclization of primary amines with dihalides using microreactors
He, Hongjie,Lin, Qi,Liu, Xiaofeng,Yang, Yongtai,Zhou, Yaming,Jia, Yu,Gao, Xiang
experimental part, p. 2512 - 2525 (2012/07/14)
(Chemical Equation Presented) A practical, rapid, and efficient reaction using microreactors for the direct N-alkylation from aniline derivatives and alkyl dihalides has been achieved in the presence of aqueous potassium carbonate at an elevated temperature. This improved synthetic methodology provides a straightforward microfluid approach to the synthesis of a variety of N-aryl azacycloalkanes. Copyright Taylor & Francis Group, LLC.
Microwave-assisted synthesis of azetidines in aqueous media
Burkett, Brendan A.,Ting, Samuel Z.,Gan, Gwendolyn C. S.,Chai, Christina L. L.
supporting information; experimental part, p. 6590 - 6592 (2011/02/23)
Simple azetidines are synthesized in good to excellent yields and high purity via cyclization of 3-(ammo-nio)propyl sulfates derived from primary amines and the cyclic sulfate of 1,3-propanediol. A feature of this methodology includes the accelerated synt
Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: Microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives
Ju, Yuhong,Varma, Rajender S.
, p. 135 - 141 (2007/10/03)
The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides a simple and straightforward one-pot approach to the synthesis of a variety of heterocycles, such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted 2,3-dihydro-1H-isoindoles, 4,5-dihydropyrazoles, pyrazolidines, and 1,2-dihydrophthalazines.
An efficient and simple aqueous N-heterocyclization of aniline derivatives: Microwave-assisted synthesis of N-aryl azacycloalkanes
Ju, Yuhong,Varma, Rajender S.
, p. 2409 - 2411 (2007/10/03)
(Chemical Equation Presented) An efficient and clean synthesis of N-aryl azacycloalkanes from alkyl dihalides and aniline derivatives has been achieved using microwave irradiation in an aqueous potassium carbonate medium. The phase separation can simplify the product isolation and reduce usage of volatile organic solvents.
