13041-75-3Relevant academic research and scientific papers
Synthesis, molecular modelling and CYP24A1 inhibitory activity of novel of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides
Taban, Ismail M.,Zhu, Jinge,DeLuca, Hector F.,Simons, Claire
, p. 4076 - 4087 (2017)
CYP24A1 (25-hydroxyvitamin D-24-hydroxylase) is a useful enzyme target for a range of medical conditions including cancer, cardiovascular and autoimmune disease, which show elevated CYP24A1 levels and corresponding reduction of calcitriol (the biologically active form of vitamin D). A series of (E)-N-(2-(1H-imidazol-1-yl)-2-(phenylethyl)-3/4-styrylbenzamides have been synthesised using an efficient synthetic route and shown to be potent inhibitors of CYP24A1 (IC50 0.11–0.35?μM) compared with the standard ketoconazole. Molecular modelling using our CYP24A1 homology model showed the inhibitors to fill the hydrophobic binding site, forming key transition metal interaction between the imidazole nitrogen and the haem Fe3+ and multiple interactions with the active site amino acid residues.
In situ generation of palladium nanoparticles: Reusable, ligand-free heck reaction in PEG-400 assisted by focused microwave irradiation
Du, Zhengyin,Zhou, Wanwei,Bai, Lin,Wang, Fen,Wang, Jin-Xian
, p. 369 - 372 (2011)
A rapid and efficient Heck coupling reaction of aryl iodides with terminal olefins was conducted in PEG-400 at 120 °C in the presence of potassium carbonate and palladium nanoparticles formed in situ from palladium chloride under focused microwave irradiation. High to excellent product yields were achieved. The reaction medium and catalyst could be easily recycled at least five times without significant loss in reactivity. Georg Thieme Verlag Stuttgart New York.
NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media
Alavi G., Seyyedeh Ameneh,Nasseri, Mohammad Ali,Kazemnejadi, Milad,Allahresani, Ali,Hussainzadeh, Mahdi
, p. 7741 - 7757 (2021/05/13)
The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is
Aminomethylpyridinequinones as new ligands for PEPPSI-type complexes
Gajda, Roman,Poater, Albert,Brotons-Rufes, Artur,Planer, Sebastian,Wo?niak, Krzysztof,Grela, Karol,Kajetanowicz, Anna
, p. 138 - 156 (2021/03/22)
A set of six new catalysts possessing quinone moieties in a pyridine ligand was synthesized and fully characterized by standard analytical techniques, including X-Ray crystallography. The results obtained in Suzuki and Mizoroki–Heck cross-coupling reactions catalyzed by quinone-based compounds were comparable to these obtained in the presence of the original PEPPSI complex designed by Organ. DFT calculations allow to see the structural and electronic factors to describe their similarity. On the other hand, steric maps and NCI plots were the tools to have a more global view of the systems studied, leaving the sphere of reactivity around the metal.
Synthesis of Pd@graphene oxide framework nanocatalyst with enhanced activity in Heck-Mizoroki cross-coupling reaction
Shekarizadeh, Arezoo,Azadi, Roya
, (2020/05/22)
A new method was developed for producing a catalyst involving a Pd nanoparticle (NP) embedded in a graphene oxide framework (Pd@GOF) with ordered macro- and mesoporous structures. First, 5,5′-diamino-2,2′-bipyridine was selected as cross-linking for covalent modification of GO nanosheets to prepare a three-dimensional (3D) framework with interlayer spaces in which well-dispersed and ultra-small Pd NPs in situ grew and embedded the framework. The synthesized nanopores 3D Pd@GOF can act as nanoreactors to help the reaction substrates thoroughly come into contact with the surface of Pd NPs, thereby exhibiting high activity toward the Heck reaction, rarely reported concerning Pd NPs supported on one-side functionalized graphene. The Pd@GOF catalyst can be used 10 times without any significant loss in the catalytic activity, confirming the long-term stability of this catalyst. Therefore, the covalently assembled GOF was proposed as a universal platform for hosting noble metal NPs to construct the desired metal@GOF nanocatalyst with improved activity and stability that can be used in a broad range of practical applications.
Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts
Filimonov, Victor D.,Krasnokutskaya, Elena A.,Kassanova, Assia Zh.,Fedorova, Valentina A.,Stankevich, Ksenia S.,Naumov, Nikolay G.,Bondarev, Alexander A.,Kataeva, Veronika A.
supporting information, p. 665 - 674 (2018/09/14)
Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.
Hedgehog pathway inhibitors of the acylthiourea and acylguanidine class show antitumor activity on colon cancer in vitro and in vivo
Vesci, Loredana,Milazzo, Ferdinando Maria,Stasi, Maria Antonietta,Pace, Silvia,Manera, Francesco,Tallarico, Carlo,Cini, Elena,Petricci, Elena,Manetti, Fabrizio,De Santis, Rita,Giannini, Giuseppe
, p. 368 - 379 (2018/08/17)
Small series of acylguanidine and acylthiourea derivatives were synthesized in gram-scale and assayed for their ability to modulate the Hh signalling pathway. In vitro studies showed a low micromolar inhibitory activity toward tumor cell lines, while the oral administration revealed an excellent ADME profile in vivo. Compound 5 emerged as the most active and safe inhibitor of colon cancer cells both in vitro and in a xenograft mouse model. Based on these data, 5 could be prioritized to further development with the perspective of clinical studies.
Chemoselective and Sequential Palladium-Catalyzed Couplings for the Generation of Stilbene Libraries via Immobilized Substrates
Traficante, Carla I.,Fagundez, Catherine,Serra, Gloria L.,Mata, Ernesto G.,Delpiccolo, Carina M. L.
supporting information, p. 225 - 229 (2016/06/01)
A versatile palladium-catalyzed tandem synthetic sequence to afford E-stilbenes libraries has been developed. Excellent regio- and stereocontrol have been achieved by means of the sequence of Hiyama and Heck cross-couplings. Undesirable homocoupling bypro
A highly active nickel-fibre complex as a catalyst for the Heck reaction
Wu, Zhi-Chuan,Yang, Quan,Chen, Meng,Liu, Li,Tao, Ting-Xian
, p. 164 - 166 (2016/04/20)
A new amidoxime fibre-nickel catalyst (AOFs-Ni(0)) was synthesised by a coordination and reduction reaction. The X-ray diffraction patterns indicated that the Ni(II) ions were reduced to Ni(0). The scanning electron microscope image showed that the Ni(0) particles which were reduced in situ had a diameter of about 300 nm. This catalyst demonstrated high activity in the Heck coupling reaction of aryl iodine and conjugated alkenes without the protection of an inert atmosphere.
Efficiency of [2 + 2] photodimerization of various stilbene derivatives within the DNA duplex scaffold
Doi, Tetsuya,Kashida, Hiromu,Asanuma, Hiroyuki
supporting information, p. 4430 - 4437 (2015/04/14)
A DNA duplex was used as a scaffold to evaluate the intrinsic reactivity of [2 + 2] photodimerization between stilbene derivatives; the duplex pre-organizes the substrates avoiding the need for an association step. Unmodified stilbenes were first introduc
