720-44-5Relevant academic research and scientific papers
Binaphthyl-prolinol chiral ligands: Design and their application in enantioselective arylation of aromatic aldehydes
Yao, Chao,Chen, Yaoqi,Sun, Ruize,Wang, Chao,Huang, Yue,Li, Lin,Li, Yue-Ming
supporting information, p. 3644 - 3655 (2021/05/04)
Binaphthyl-prolinol ligands were designed and applied in enantioselective arylation of aromatic aldehydes and sequential arylation-lactonization of methyl 2-formylbenzoate. Under optimized conditions, the reactions provided the desired diarylmethanols and 3-aryl phthalides in up to 96% yields with up to 99% ee and up to 89% yields with up to 99% ee, respectively. In particular, essentially optically pure 3-aryl phthalides (over 99% ee) were obtained in large quantities through recrystallization. This journal is
Enantioselective α-Arylation of Primary Alcohols under Sequential One-Pot Catalysis
Aleksandrova, Maiia,Dydio, Pawe?,Lainer, Bruno,Lichosyt, Dawid
, p. 9253 - 9262 (2021/06/30)
Secondary benzylic alcohols and diarylmethanols are common structural motifs of biologically active and medicinally relevant compounds. Here we report their enantioselective synthesis by α-arylation of primary aliphatic and benzylic alcohols under sequential catalysis integrating a Ru-catalyzed hydrogen transfer oxidation and a Ru-catalyzed nucleophilic addition. The method can be applied to various alcohols and aryl nucleophiles tolerating a range of functional groups, including secondary alcohols, ketones, alkenes, esters, NH amides, tertiary amines, aryl halides, and heterocycles.
Melamine-Based Porous Organic Polymers Supported Pd(II)-Catalyzed Addition of Arylboronic Acids to Aromatic Aldehydes
Shen, Kai,Wen, Min,Fan, Chaogang,Lin, Shaohui,Pan, Qinmin
, p. 2612 - 2621 (2021/01/15)
Abstract: A new type melamine-based porous organic polymers (SZU-1) has been synthesized with melamine and 2,2′-bipyridyl-5,5′-dialdehyde by a one-pot method and fully characterized. Divalent palladium salts were coordinated to this polymer network which successfully catalyzed the nucleophilic addition reaction of arylboronic acids to aromatic aldehydes. With only 1.0?mol% heterogeneous catalyst loading, high reaction yields (>?85%) can be achieved in most cases. The scope of substrates was also investigated and the catalyst showed universal applicability. Graphic Abstract: The loose and porous melamine-based porous organic polymers (SZU-1) are synthesized by melamine and 2,2′-bipyridyl-5,5′-dialdehyde. The performance of SZU-1 was characterized and most of the substrates achieved high yield (> 85%) in the catalytic performance test.[Figure not available: see fulltext.]
Light-driven MPV-type reduction of aryl ketones/aldehydes to alcohols with isopropanol under mild conditions
Cao, Dawei,Xia, Shumei,Pan, Pan,Zeng, Huiying,Li, Chao-Jun,Peng, Yong
supporting information, p. 7539 - 7543 (2021/10/12)
Alcohols are versatile structural motifs of pharmaceuticals, agrochemicals and fine chemicals. With respect to green chemistry, the development of more sustainable and cost-efficient processes for converting ketones/aldehydes to alcohols is highly desired. Herein, a direct light-driven strategy for reducing ketones/aldehydes to alcohols using isopropanol as the reducing agent and solvent, in the presence of t-BuOLi, under an air atmosphere at room temperature is developed. This operationally simple light-promoted Meerwein-Ponndorf-Verley (MPV) type reduction can be used to produce various benzylic alcohol derivatives as well as applied to bioactive molecules and PEEK model compounds, demonstrating its application potential.
Methylene-Linked Bis-NHC Half-Sandwich Ruthenium Complexes: Binding of Small Molecules and Catalysis toward Ketone Transfer Hydrogenation
Botubol-Ares, José Manuel,Cordón-Ouahhabi, Safa,Moutaoukil, Zakaria,Collado, Isidro G.,Jiménez-Tenorio, Manuel,Puerta, M. Carmen,Valerga, Pedro
supporting information, p. 792 - 803 (2021/04/06)
The complex [Cp*RuCl(COD)] reacts with LH2Cl2 (L = bis(3-methylimidazol-2-ylidene)) and LiBun in tetrahydrofuran at 65 °C furnishing the bis-carbene derivative [Cp*RuCl(L)] (2). This compound reacts with NaBPh4 in MeOH under dinitrogen to yield the labile dinitrogen-bridged complex [{Cp*Ru(L)}2(μ-N2)][BPh4]2 (4). The dinitrogen ligand in 4 is readily replaced by a series of donor molecules leading to the corresponding cationic complexes [Cp*Ru(X)(L)][BPh4] (X = MeCN 3, H2 6, C2H4 8a, CH2CHCOOMe 8b, CHPh 9). Attempts to recrystallize 4 from MeNO2/EtOH solutions led to the isolation of the nitrosyl derivative [Cp*Ru(NO)(L)][BPh4]2 (5), which was structurally characterized. The allenylidene complex [Cp*Ru═C═C═CPh2(L)][BPh4] (10) was also obtained, and it was prepared by reaction of 2 with HCCC(OH)Ph2 and NaBPh4 in MeOH at 60 °C. Complexes 3, 4, and 6 are efficient catalyst precursors for the transfer hydrogenation of a broad range of ketones. The dihydrogen complex 6 has proven particularly effective, reaching TOF values up to 455 h-1 at catalyst loadings of 0.1% mol, with a high functional group tolerance on the reduction of a broad scope of aryl and aliphatic ketones to yield the corresponding alcohols.
Tunable System for Electrochemical Reduction of Ketones and Phthalimides
Chen, Gong,Qiao, Tianjiao,Wang, Yaxin,Zhang, Jian,Zhao, Jianyou
supporting information, p. 3297 - 3302 (2021/10/14)
Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.
Synthesis and biological evaluation of 1‐(Diarylmethyl)‐1h‐1,2,4‐triazoles and 1‐(diarylmethyl)‐1h‐imidazoles as a novel class of anti‐mitotic agent for activity in breast cancer
Ana, Gloria,Kelly, Patrick M.,Malebari, Azizah M.,Noorani, Sara,Nathwani, Seema M.,Twamley, Brendan,Fayne, Darren,O’boyle, Niamh M.,Zisterer, Daniela M.,Pimentel, Elisangela Flavia,Endringer, Denise Coutinho,Meegan, Mary J.
, p. 1 - 59 (2021/03/16)
We report the synthesis and biochemical evaluation of compounds that are designed as hybrids of the microtubule targeting benzophenone phenstatin and the aromatase inhibitor letrozole. A preliminary screening in estrogen receptor (ER)‐positive MCF‐7 breast cancer cells identified 5‐((2H‐1,2,3‐triazol‐1‐yl)(3,4,5‐trimethoxyphenyl)methyl)‐2‐methoxyphenol 24 as a potent antiproliferative compound with an IC50 value of 52 nM in MCF‐7 breast cancer cells (ER+/PR+) and 74 nM in triple‐negative MDA‐MB‐231 breast cancer cells. The compounds demonstrated significant G2/M phase cell cycle arrest and induction of apoptosis in the MCF‐7 cell line, inhibited tubulin polymerisation, and were selective for cancer cells when evaluated in non-tumorigenic MCF‐10A breast cells. The immunofluorescence staining of MCF‐7 cells confirmed that the compounds targeted tubulin and induced multinucleation, which is a recognised sign of mitotic catastrophe. Computational docking studies of compounds 19e, 21l, and 24 in the colchicine binding site of tubulin indicated potential binding conformations for the compounds. Compounds 19e and 21l were also shown to selectively inhibit aromatase. These compounds are promising candidates for development as antiproliferative, aromatase inhibitory, and microtubule‐disrupting agents for breast cancer.
Enhanced catalytic activity of one-dimensional CdS @TiO2 core-shell nanocomposites for selective organic transformations under visible LED irradiation
Eskandari, Parvin,Kazemi, Foad,Ramdar, Moosa,Zand, Zahra
, (2021/07/10)
In this study, we are interested in the photocatalytic activity under visible LED irradiation of one- dimensional (1D) CdS @TiO2 core–shell nanocomposites (CSNs) prepared through a facile and convenient method. For the synthesis of 1D CdS@TiO2 core/shell structure, titania source (Tetrabutyl titanate) was hydrolyzed by water vapor transmission on the surface of CdS nanowires (NWs) which were prepared via solvothermal method. The characterization of 1D CdS@TiO2 core–shell nanocomposites (CdS@TiO2 CSNs) was performed using X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), UV–Vis spectroscopy, and UV–Vis diffuse reflectance spectroscopy (DRS). The as-synthesized sample was utilized for the selective reduction of nitro compounds to benzimidazole and anilide, and also the reduction of benzophenones to alcohol under blue LED irradiation. The 1D CdS@TiO2 CSNs exhibited enhanced photoactivity compared with the pure TiO2, CdS nanowires and commercial TiO2-P25. The excellent reusability of the photocatalyst was examined for six runs. The results demonstrated that the prepared sample has the potential to provide a promising visible light-driven photocatalyst for other organic transformations.
Structure-Based Design of High-Affinity Fluorescent Probes for the Neuropeptide Y Y1Receptor
Betschart, Martin U.,Gleixner, Jakob,Keller, Max,Koch, Pierre,Kopanchuk, Sergei,Rinken, Ago,Schollmeyer, Dieter,Tahk, Maris-Johanna,Weinhart, Michael,Lüdeke, Steffen,Laasfeld, T?nis,Müller, Christoph
, (2022/03/27)
The recent crystallization of the neuropeptide Y Y1 receptor (Y1R) in complex with the argininamide-type Y1R selective antagonist UR-MK299 (2) opened up a new approach toward structure-based design of nonpeptidic Y1R ligands. We designed novel fluorescent probes showing excellent Y1R selectivity and, in contrast to previously described fluorescent Y1R ligands, considerably higher (～100-fold) binding affinity. This was achieved through the attachment of different fluorescent dyes to the diphenylacetyl moiety in 2 via an amine-functionalized linker. The fluorescent ligands exhibited picomolar Y1R binding affinities (pKi values of 9.36-9.95) and proved to be Y1R antagonists, as validated in a Fura-2 calcium assay. The versatile applicability of the probes as tool compounds was demonstrated by flow cytometry- and fluorescence anisotropy-based Y1R binding studies (saturation and competition binding and association and dissociation kinetics) as well as by widefield and total internal reflection fluorescence (TIRF) microscopy of live tumor cells, revealing that fluorescence was mainly localized at the plasma membrane.
Nickel-Mediated Enantiospecific Silylation via Benzylic C-OMe Bond Cleavage
Balakrishnan, Venkadesh,Murugesan, Vetrivelan,Chindan, Bincy,Rasappan, Ramesh
supporting information, p. 1333 - 1338 (2021/02/20)
Benzylic stereocenters are found in bioactive and drug molecules, as enantiopure benzylic alcohols have been used to build such a stereogenic center, but are limited to the construction of a C-C bond. Silylation of alkyl alcohols has the potential to build bioactive molecules and building blocks; however, the development of such a process is challenging and unknown. Herein, we describe an unprecedented AgF-assisted nickel catalysis in the enantiospecific silylation of benzylic ethers.
