70-55-3Relevant articles and documents
Cellular AND Gates: Synergistic Recognition to Boost Selective Uptake of Polymeric Nanoassemblies
Fernandez, Ann,Gao, Jingjing,Thayumanavan, S.,Wu, Peidong,Zhuang, Jiaming
, p. 10456 - 10460 (2020)
The development of nanoparticle-based biomedical applications has been hampered due to undesired off-target effects. Herein, we outline a cellular AND gate to enhance uptake selectivity, in which a nanoassembly–cell interaction is turned on, only in the concurrent presence of two different protein functions, an enzymatic reaction (alkaline phosphatase, ALP) and a ligand–protein (carbonic anhydrase IX, CA IX) binding event. Selective uptake of nanoassemblies was observed in cells that overexpress both of these proteins (unicellular AND gate). Interestingly, selective uptake can also be achieved in CA IX overexpressed cells, when cocultured with ALP overexpressed cells, where the nanoassembly presumably acts as a mediator for cell–cell communication (bicellular AND gate). This logic-gated cellular uptake could find use in applications such as tumor imaging or theranostics.
Synthesis of 8-Alkoxy-5 H-isochromeno[3,4- c]isoquinolines and 1-Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C-H Functionalization of Benzimidates with 4-Diazoisochroman-3-imines and 4-Diazoisoquinolin-3-ones
Li, Zhenmin,Lu, Ping,Wang, Yanguang,Xie, Jianwei
, p. 5525 - 5535 (2020)
Rh(III)-catalyzed C-H activation/annulation of benzimidates with 4-diazoisochroman-3-imines furnished 8-alkoxy-5H-isochromeno[3,4-c]isoquinolines in moderate to excellent yields with a broad range of substrate scope. The reaction was carried out under mild reaction conditions and could be scaled up with practical usage. Similar reaction between benzimidates and 4-diazoisoquinolin-3-ones provided 1-alkoxy-4-arylisoquinolin-3-ols in excellent yields. Moreover, the synthesized products could be conveniently transformed to the corresponding heterocycles with a 1,8-naphthyridinone or isochromenopyridinone core, which are privileged structures in medicinal chemistry.
Anisole alkylation with N-arenesulfonylimines of dichloro(phenyl)acetaldehyde and derivatives thereof
Drozdova,Mirskova
, p. 819 - 821 (2001)
N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron t
Structural, vibrational spectra and normal coordinate analysis for two tautomers of 4(5)-(2′-furyl)-imidazole
Ledesma,Zinczuk,Gonzalez, J.J. Lopez,Altabef, A. Ben,Brandan
, p. 587 - 597 (2010)
We have synthesized both the 4 and 5 tautomeric forms of 4(5)-(2′-furyl)-imidazole (1) and investigated their molecular vibrations by infrared and Raman spectroscopies as well as by calculation based on the density functional theory (DFT) approach. Examination of the temperature dependence of IR intensity revealed the band characteristics of the 4 and 5 tautomersof(1).Comparisonofexperimentalandcalculatedchemicalshiftsinnucl earmagneticresonance(NMR)spectroscopy was made in order to identify the two tautomeric forms. The assignment of vibrational normal modes was performed, and the forcefieldobtainedreproduced theexperimentalvibrationalwavenumbers with a root mean-squaredeviation (RMSD)value of ca. 13 cm-1 for both tautomers. The natural bond orbital (NBO) study reveals the characteristics of the electronic delocalization of the two tautomeric structures.
Formation and Isolation of the Disulphide Dication of 1,5-Dithiacyclo-octane in the Reactions of the Corresponding S-Oxide and S-(N-tosylimide) in Concentrated Sulphuric Acid
Furukawa, Naomichi,Kawada, Akira,Kawai, Tsutomu
, p. 1151 - 1152 (1984)
The disulphide dication of 1,5-dithiacyclo-octane was generated in the reaction of the corresponding S-oxide and S-(N-tosylimide) with conc.H2SO4 and isolated in crystalline form.
Cyclopropyl aziridines: Solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene
Silverberg, Lee J.,Rabb, Javon M.,Reno, Joseph M.,He, Gang
, p. 193 - 199 (2014)
The N-tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis-3-carene-N-tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8, and both rings were opened in 4, whereas only the aziridine was opened in 8. This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.
Data-Driven Identification of Hydrogen Sulfide Scavengers
Yang, Chun-tao,Wang, Yingying,Marutani, Eizo,Ida, Tomoaki,Ni, Xiang,Xu, Shi,Chen, Wei,Zhang, Hui,Akaike, Takaaki,Ichinose, Fumito,Xian, Ming
, p. 10898 - 10902 (2019)
Hydrogen sulfide (H2S) is an important signaling molecule whose up- and down-regulation have specific biological consequences. Although significant advances in H2S up-regulation, by the development of H2S donors, have been achieved in recent years, precise H2S down-regulation is still challenging. The lack of potent/specific inhibitors for H2S-producing enzymes contributes to this problem. We expect the development of H2S scavengers is an alternative approach to address this problem. Since chemical sensors and scavengers of H2S share the same criteria, we constructed a H2S sensor database, which summarizes key parameters of reported sensors. Data-driven analysis led to the selection of 30 potential compounds. Further evaluation of these compounds identified a group of promising scavengers, based on the sulfonyl azide template. The efficiency of these scavengers in in vitro and in vivo experiments was demonstrated.
Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls
Bai, Jiaxing,Ding, Pin,Han, Lingbo,Liu, Jingjing,Luan, Xinjun
, (2022/03/19)
Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles. Noteworthily, a linchpin for this domino reaction was the judicious selection of both the amino-sources and Pd(0)-catalysts for enabling the prerequisite oxidative addition of aryl halides to Pd(0)-species in the presence of hydroxylamines with a labile N-O bond. [Figure not available: see fulltext.].
Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets
Li, Tingting,Xu, Bo
supporting information, p. 2673 - 2678 (2021/08/03)
Main observation and conclusion: We describe a practical and general protocol for immobilization of heterogeneous catalysts to mechanically robust porous ultra-high molecular weight polyethylene tablets using inter-facial Lifshitz-van der Waals Interactions. Diverse types of powderous catalysts, including Cu, Pd/C, Pd/Al2O3, Pt/C, and Rh/C have been immobilized successfully. The immobilized catalysts are mechanistically robust towards stirring in solutions, and they worked well in diverse synthetic reactions. The immobilized catalyst tablets are easy to handle and reused. Moreover, the metal leaching of immobilized catalysts was reduced significantly.
Inhibitory Evaluation and Molecular Docking Analysis of Benzenesulfonamides on Carbonic Anhydrase II
Zhang,Wei,Liu,Wu,Xuan
, p. 261 - 269 (2021/03/23)
Abstract: Sulfonamides is an important class of compounds, which can be used as carbonic anhydrase inhibitors. Nine different benzenesulfonamide compounds were synthesized, and their inhibitory effects on carbonic anhydrase II were studied by esterase method and molecular docking. The results showed that compounds (IId)–(IIg) with nitro and acetamide groups on the benzene ring exhibited excellent carbonic anhydrase II inhibitory activities. Molecular docking showed that compared with the control inhibitor acetazolamide, the compounds (IId)–(IIg) docked at the carbonic anhydrase II active site and showed higher binding energy and stronger binding ability. The physical and chemical properties of all compounds were studied by Molinspiration, which showed outstanding drug-like properties and ADME properties. Cytotoxicity assay results showed that compounds (IIe) and (IIf) were almost non-toxic to HepG2 and RAW264.7 cells. In conclusion, the compounds (IIe) and (IIf) have a certain application prospect as new inhibitors of carbonic anhydrase II.