554-84-7Relevant academic research and scientific papers
Induction of structure and function in a designed peptide upon adsorption on a silica nanoparticle
Lundqvist, Martin,Nygren, Patrik,Jonsson, Bengt-Harald,Broo, Klas
, p. 8169 - 8173 (2006)
(Chemical Equation Presented) Small change: Nanoparticles can induce a functional helix from an unstructured peptide (see picture). The ability to generate stable, well-defined structures on surfaces opens up the possibility of creating nanosystems with a variety of functionalities, which is demonstrated by the introduction of a catalytic site for ester hydrolysis.
Kinetic and mechanistic investigation of the aminolysis of 3-methoxyphenyl 3-nitrophenyl thionocarbonate, 3-chlorophenyl 3-nitrophenyl thionocarbonate, and bis(3-nitrophenyl) thionocarbonate
Castro, Enrique A.,Galvez, Angelique,Leandro, Leonardo,Santos, Jose G.
, p. 4309 - 4315 (2002)
The reactions of the title thionocarbonates (6, 7, and 8, respectively) with a series of secondary alicyclic amines are subjected to a kinetic investigation in 44 wt % ethanol-water, 25.0 °C, ionic strength 0.2 M (KCl). Under excess amine, pseudo-first-order rate coefficients (kobsd) are obtained for all reactions. Reactions of substrates 6 and 7 with piperidine and of thionocarbonate 8 with the same amine and piperazine, 1-(2-hydroxyethyl)piperazine, and morpholine show linear kobsd vs [amine] plots, with slopes (k1) independent of pH. On the other hand, these plots are nonlinear upward for the reactions of substrates 6 and 7 with all the amines, except piperidine, and also for the reactions of compound 8 with 1-formylpiperazine and piperazinium ion. For all these reactions a mechanistic scheme is proposed with the formation of a zwitterionic tetrahedral intermediate (T±), which can transfer a proton to an amine to give an anionic intermediate (T-). Rate and equilibrium microcoefficients of this scheme, K1, k-1, K1, (= k1/k-1), and k2, are obtained by fitting the nonlinear plots through an equation derived from the scheme. The Broensted-type plots for k1 are linear with slopes β1 = 0.19, 0.21, and 0.26 for the aminolysis of 6, 7, and 8, respectively. This is consistent with the hypothesis that the formation of T± (k1 (k1 step) is the rate-determining step. The k1 values for these reactions follow the sequence 8 > 7 > 6, consistent with the sequence of the electron-withdrawing effects from the substituents on the nonleaving group of the substrates. The k1 values for the aminolysis of 6, 7, and 8 are smaller than those for the same aminolysis of 3-methoxyphenyl, 3-chlorophenyl, and 4-cyanophenyl 4-nitrophenyl thionocarbonates (2, 3, and 4, respectively). The k2 values (expulsion of the nucleofuge from T±) increase as the electron withdrawal from the nonleaving group increases. These values are smaller for the aminolysis of 6, 7, and 8 compared to those for the same aminolysis of 2, 3, and 4, respectively.
The Rearrangement of Aromatic Nitro Compounds. Part 2. The Rearrangement os Substituted Nitrophenols in Trifluoromethanesulphonic Acid
Bullen, John V.,Ridd, John H.
, p. 1675 - 1679 (1990)
o-Nitrophenols with an additional substituent (Y = NO2, Cl, or Me) in the 3-position rearrange in trifluoromethanesulphonic acid at 100 deg C to give mainly the product with the nitro group in the opposite ortho position; no more than 1-4percent of other products are formed.The reactions give first-order kinetics, are acid-catalysed and (at least when Y = NO2) are intramolecular.The rate of rearrangement varies with the 3-substituent in the order Me > Cl > NO2.The results are discussed in terms of a rate-determining migration of the nitro group in the Wheland intermediate formed by protonation at the 2-position.A much slower rearrangement occurs with 3,4-dinitrophenol under the same conditions to give a small yield of 2,5-dinitrophenol accompanied by decomposition of the substrate.
Highly recyclable Ti0.97Ni0.03O1.97catalyst coated on cordierite monolith for efficient transformation of arylboronic acids to phenols and reduction of 4-nitrophenol
Hegde, M. S.,Prasanna,Usha, K. M.
supporting information, p. 14223 - 14234 (2021/10/25)
A stable Ni2+substituted TiO2catalyst (Ti0.97Ni0.03O1.97) has been synthesized by a solution combustion method with an average crystallite size of 7.5 nm. Ti1?xNixO2?x(x= 0.01-0.06) crystallizes in the TiO2anatase structure with Ni2+substituted in Ti4+ion sites and Ni taking a nearly square planar geometry. This catalyst is found to be highly active in the transformation of diverse arylboronic acids to the corresponding phenols. The catalyst coated cordierite monolith can even be recycled for up to 20 cycles with a cumulative TOF of 1.8 × 105h?1. In scale-up reactions, various phenols are synthesized by employing a single cordierite monolith. It also shows high performance in the reduction of 4-nitrophenol.
Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols
Upadhyay, Rahul,Singh, Deepak,Maurya, Sushil K.
supporting information, p. 3925 - 3931 (2021/08/24)
A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.
The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes
Badgoti, Ranveer Singh,Dandia, Anshu,Parewa, Vijay,Rathore, Kuldeep S.,Saini, Pratibha,Sharma, Ruchi
, p. 18040 - 18049 (2021/05/29)
An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.
Pyroptosis drug prodrug, preparation method thereof and pyroptosis drug
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Paragraph 0064, (2021/06/13)
The invention discloses a pyroptosis drug prodrug, a preparation method thereof and a pyroptosis drug. The pyroptosis drug prodrug provided by the invention can cause mitochondria damage, release cytochrome c and activate Caspase3 to shear GSDME by targeting mitochondria, so that pyroptosis of cells occurs. The prodrug (NCyNH2) has selectivity to tumor cells, damage to normal cells is reduced, and the activation condition of the prodrug (NCyNH2) can be detected through recovery of self-fluorescence. After intratumor administration, the prodrug can effectively regulate the tumor immune microenvironment and activate T cell mediated anti-tumor immune response. The molecule has huge application prospects in the aspects of mitochondrial targeting, cell respiration inhibition, pyroptosis induction, tumor immune microenvironment improvement, T cell mediated anti-tumor immune response activation and the like.
Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid
Mélin, Léa,Abdullayev, Shuay,Fnaiche, Ahmed,Vu, Victoria,González Suárez, Narjara,Zeng, Hong,Szewczyk, Magdalena M.,Li, Fengling,Senisterra, Guillermo,Allali-Hassani, Abdellah,Chau, Irene,Dong, Aiping,Woo, Simon,Annabi, Borhane,Halabelian, Levon,LaPlante, Steven R.,Vedadi, Masoud,Barsyte-Lovejoy, Dalia,Santhakumar, Vijayaratnam,Gagnon, Alexandre
, p. 2982 - 3002 (2021/08/03)
The YAP-TEAD transcriptional complex is responsible for the expression of genes that regulate cancer cell growth and proliferation. Dysregulation of the Hippo pathway due to overexpression of TEAD has been reported in a wide range of cancers. Inhibition of TEAD represses the expression of associated genes, demonstrating the value of this transcription factor for the development of novel anti-cancer therapies. We report herein the design, synthesis and biological evaluation of LM98, a flufenamic acid analogue. LM98 shows strong affinity to TEAD, inhibits its autopalmitoylation and reduces the YAP-TEAD transcriptional activity. Binding of LM98 to TEAD was supported by 19F-NMR studies while co-crystallization experiments confirmed that LM98 is anchored within the palmitic acid pocket of TEAD. LM98 reduces the expression of CTGF and Cyr61, inhibits MDA-MB-231 breast cancer cell migration and arrests cell cycling in the S phase during cell division.
An efficient Ti0.95Cu0.05O1.95 catalyst for ipso – hydroxylation of arylboronic acid and reduction of 4-nitrophenol
Bhat, Shrikanth K,Dasappa, Jagadeesh Prasad,Hegde, M. S.,Prasanna
, (2021/08/12)
A stable, active and selective Ti0.95Cu0.05O1.95 catalyst, crystallized in anatase TiO2 structure with 5% Cu2+ ions substituted for Ti4+ ions with 5% oxide ion vacancy has been synthesized by solution combustion method. The catalyst was coated over a cordierite monolith (Mg2Al4Si5O18) by solution combustion method. By the first principle density functional theory (DFT) calculations, 48 atoms bulk structure has been optimized and density of states (DOS) has been calculated. Ti – O bond distribution in Ti0.95Cu0.05O1.95 has been compared with pure TiO2. Bond distribution analysis has shown longer Cu – O and Ti – O bonds compared to those in CuO and TiO2 creating Cu2+ and oxide ion vacancy as electrophilic and nucleophilic active sites, respectively. This catalyst was found to be very active for ipso – hydroxylation of arylboronic acid and 4-nitrophenol reduction reactions at room temperature. Catalyst coated cordierite monolith was used in the recycling process of the reaction for 20 cycles and cumulative turnover frequency was found to be 184,840 h?1. Ti0.95Cu0.05O1.95 catalyst coated on cordierite monolith enhanced the rate of the reaction compared to powder catalyst and made the handling and recycling of the catalyst very easy. Graphic abstract: [Figure not available: see fulltext.]
HDAC and CTSL responsive diagnosis and treatment integrated material and preparation method and application thereof
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Paragraph 0061; 0067; 0074-0075, (2021/07/01)
The invention belongs to the technical field of biological medicine and fluorescence detection, and particularly relates to an HDAC and CTSL responsive diagnosis and treatment integrated material and a preparation method and application thereof. The HDAC and CTSL responsive diagnosis and treatment integrated material is prepared from an anti-tumor drug Cy-NH2 and provided with a large number of HDAC and CTSL specific response bonds, enzyme response is generated in tumor cells with high HDAC and CTSL expression to be broken, so that the anti-tumor drug Cy-NH2 is rapidly released into the tumor cells, and the advantage of targeted drug delivery is achieved; and in addition, Cy-NH2 can be used for imaging tumor cells under the excitation of a specific wavelength, and has huge clinical application potential.
