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Xiubao Chang, Qinqin Xu, Yuexian Hou, Cynthia Li, Ye Xu, A Keith Stewart
Immunomodulatory drugs (IMiDs) are profoundly active compounds in the treatment of patients with multiple myeloma (MM). However, despite the fact that treatment with IMiDs has dramatically improved survival for patients with MM, the majority of MM patients develop IMiDs resistance over time. We have found that expression of functional cereblon is required for IMiDs' action. In addition, it has been reported that cells expressing high levels of cereblon are resistant to proteasome inhibitor, implying that patients with high levels of cereblon should be resistant to proteasome inhibitor...
September 17, 2017: International Journal of Molecular Sciences
Chun-Tian Li, Hui Liu, Yan-Jun Xu, Chong-Dao Lu
Diastereoselective aldol reaction of N-tert-butanesulfinyl imidates under typical hard enolization conditions is reported. Potassium bis(trimethylsilyl)amide (KHMDS) effectively promotes the aldol reaction of α-aryl- and α-alkyl-substituted imidates, providing anti-aldol adducts in high yields with good to excellent diastereoselectivities. In the case of α-aryl imidates, high conversion depends on adding trimethylsilyl chloride (TMSCl) to the reaction mixture. In the presence of a suitable Lewis acid, cyclohexanone is a good electrophile in the aldol reaction of imidates...
September 19, 2017: Journal of Organic Chemistry
Mansoureh Shojaatalhosseini, Khalid Elamin, Jan Swenson
In this study we have used nonocomposite polymer electrolytes, consisting of poly(ethylene oxide) (PEO), δ-Al2O3 nanoparticles and lithium bis(trifluoromethanesolfonyl)imide (LiTFSI) salt (with 4 wt% δ-Al2O3 and PEO:Li ratios of 16:1 and 8:1), and added different amounts of the ionic liquid 1-butyl-3-methylimidazolium bis(trifluoromethanesolfonyl)imide (BMITFSI). The aim was to elucidate whether the ionic liquid is able to dissociate the Li-ions from the ether oxygens and thereby decouple the ionic conductivity from the segmental polymer dynamics...
September 19, 2017: Journal of Physical Chemistry. B
Li Wang, Gang Wang, Congdi Shang, Rui Kang, Yu Fang
A naphthalimide-based low-molecular mass fluorophore (NA) was designed and synthesized by introducing an azetidine unit onto the aromatic ring of the compound as an electron-donating structure, and a hydrophilic (2-(2-aminoethylamino)ethanol) moiety into the 'N-imide site' of the core structure. UV-vis absorption and fluorescence measurements revealed that the fluorophore is soluble in water, and shows a fluorescent quantum yield of ~20% and lifetime of ~3.7 ns in the solvent within a wide pH range. Moreover, the fluorescence emission and anisotropy of the fluorophore as produced are both dependent upon the viscosity and polarity of the medium...
September 19, 2017: ACS Applied Materials & Interfaces
Takeshi Nanjo, Emilio Carlos de Lucca, M Christina White
Amide-containing molecules are ubiquitous in natural products, pharmaceuticals, and materials science. Due to their intermediate electron-richness, they are not amenable to any of the previously developed N-protection strategies known to enable remote aliphatic C-H oxidations. Using information gleaned from a systematic study of the main features that makes remote oxidations of amides in peptide settings possible, we developed an imidate salt protecting strategy that employs methyl trifluoromethanesulfonate (MeOTf) as a reversible alkylating agent...
September 18, 2017: Journal of the American Chemical Society
Jeroen Sniekers, Pieter Geysens, João C Malaquías, Tom Vander Hoogerstraete, Luc Van Meervelt, Jan Fransaer, Koen Binnemans
Cobalt(ii)-containing liquid metal salts (LMS) with N-alkylimidazole ligands and bis(trifluoromethanesulfonyl)imide (bistriflimide, Tf2N(-)) or methanesulfonate (mesylate, OMs(-)) anions were synthesized and characterized. The chain length of the alkyl side chain on the imidazole ligand was varied. All compounds were characterized using CHN analysis, DSC and FTIR measurements. Single-crystal X-ray diffraction measurements were performed on six of the compounds for which single crystals of good quality could be obtained...
September 18, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
Rajendra Kumar Mallick, Baskaran Prabagar, Akhila Kumar Sahoo
A novel and straightforward protocol is demonstrated for the synthesis of highly substituted oxazole from readily accessible ynamides in the presence of ytterbium(III) trifluoromethanesulfonate [Yb(OTf)3], N-iodosuccinimide (NIS), and acetonitrile. Multiple oxazole skeletons in the aryl-periphery are constructed in a single operation for the first time. The hydroamidation and iodo-imidation of ynamides to tri- and tetra-substituted ketene aminals is exemplified. An isotope labeling experiment is used to identify the oxygen source in this transformation...
September 18, 2017: Journal of Organic Chemistry
Guangliang Hu, Gaind P Pandey, Qingfeng Liu, Radhika S Anaredy, Chunrui Ma, Ming Liu, Jun Li, Scott K Shaw, Judy Z Wu
Electrochemical effects manifest as nonlinear responses to an applied electric field in electrochemical devices, and are linked intimately to the molecular orientation of ions in the electric double layer (EDL). Herein, we probe the origin of the electrochemical effect using a double-gate graphene field effect transistor (GFET) of ionic liquid N,N-diethyl-N-(2-methoxyethyl)-N-methylammonium bis-(trifluoromethylsulfonyl)-imide (DEME-TFSI) top-gate, paired with a ferroelectric Pb0.92La0.08Zr0.52Ti0.48O3 (PLZT) back-gate of compatible gating efficiency...
September 18, 2017: ACS Applied Materials & Interfaces
Ningning Bi, Chenghe Xiong, Guoxia Jin, Zhongwu Guo, Guofeng Gu
The trisaccharide repeating unit of an O-antigen derived from Burkholderia cenocepacia and its dimer, i.e., α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (1) and α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-(1 → 4)-α-L-Rhap-(1 → 3)-α-D-GalpNAc-(1 → 3)-β-D-GalpNAc-O(CH2)3N3 (2), respectively, were synthesized via a highly convergent strategy. Glycosylation of galactosaminyl acceptor 4 with galactosaminyl trichloroacetimidate donor 5 was followed by condensation of resulting disaccharide acceptor 12 with rhamnosyl imidate donor 6 to furnish stereoselectively trisaccharyl thioglycoside 3, which was used as a key and common glycosyl donor for the construction of both 1 and 2...
September 8, 2017: Carbohydrate Research
Kambiz Varmira, Omid Abdi, Mohammad-Bagher Gholivand, Hector C Goicoechea, Ali R Jalalvand
Acrylamide (AA) is a neurotoxin and carcinogen which is mainly formed in foods containing large quantities of starch processed at high temperatures and its determination is very important to control the quality of foods. In this work, a novel electrochemical biosensor based on hemoglobin-dimethyldioctadecylammonium bromide (HG-DDAB)/platinum-gold-palladium three metallic alloy nanoparticles (PtAuPd NPs)/chitosan-1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (Ch-IL)/multiwalled carbon nanotubes-IL (MWCNTs-IL)/glassy carbon electrode (GCE) is proposed for ultrasensitive determination of AA in food samples...
January 1, 2018: Talanta
You Yang, Biao Yu
Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C-C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates...
September 15, 2017: Chemical Reviews
Wei Huang, Hui Liu, Yan-Jun Xu, Chong-Dao Lu
A single-flask reaction of silyllithium, α-keto N-tert-butanesulfinyl imidates and aldehydes has been developed for diastereoselective synthesis of α,β-dihydroxy acid derivatives. In this reaction, nucleophilic addition of silyllithium to chiral α-keto imidates followed by silyl migration forms chiral aza-enolates, which react diastereoselectively with aldehydes. Subsequent [1,4]-O to O silyl migration affords α-substituted β-(silyoxy)-α-hydroxy imidates.
September 14, 2017: Journal of Organic Chemistry
Anamarija Briš, Mateja Đud, Davor Margetić
The mechanochemical N-alkylation of imide derivatives was studied. Reactions under solvent-free conditions in a ball mill gave good yields and could be put in place of the classical solution conditions. The method is general and can be applied to various imides and alkyl halides. Phthalimides prepared under ball milling conditions were used in a mechanochemical Gabriel synthesis of amines by their reaction with 1,2-diaminoethane.
2017: Beilstein Journal of Organic Chemistry
Tao Xu, Tobias Waehler, Julia Vecchietti, Adrian Bonivardi, Tanja Bauer, Johannes Schwegler, Peter Steffen Schulz, Peter Wasserscheid, Jörg Libuda
We have performed surface science model studies scrutinizing the interaction of ester-functionalized ionic liquids(ILs) with atomically defined Co3O4(111) and CoO(100) surfaces. Thin films of three ILs, 3-butyl-1-methyl imidazolium bis(trifluoromethyl-sulfonyl) imide ([BMIM][NTf2]), 3-(4-methoxyl-4-oxobutyl)-1-methylimidazolium bis(trifluoromethyl-sulfonyl) imide ([MBMIM][NTf2]), and 3-(4-iso¬propoxy-4-oxobutyl)-1-methylimidazolium bis(trifluoromethyl-sulfonyl) imide ([IPBMIM][NTf2]), were deposited on these surfaces by physical vapor deposition...
September 12, 2017: Chemphyschem: a European Journal of Chemical Physics and Physical Chemistry
Pascal Pigeon, Yong Wang, Siden Top, Feten Najlaoui, Maria Concepcion Garcia Alvarez, Jérôme Bignon, Michael James McGlinchey, Gerard Jaouen
Ferrociphenols are known to display anticancer properties by original mechanisms dependent on redox properties and generation of active metabolites such as quinone methides. Recent studies have highlighted the positive impact of oxidative stress on chemosensitivity and prognosis of ovarian cancer patients. Ovarian adenocarcinomas are shown to be an excellent model for defining the impact of selected ferrociphenols as new therapeutic drugs for such cancers. This work describes the syntheses and preliminary mechanistic research of unprecedented multitargeting heterocyclic ferrociphenols bearing either a succinimidyl or phthalimidyl group that show exceptional antiproliferative behavior against epithelial ovarian cancer cells resistant to cisplatin...
September 12, 2017: Journal of Medicinal Chemistry
Maryam A Jordaan, Michael Shapi
This study sought to investigate the solvent-dependency on the photolysis of efavirenz to gain insight into the photoprocesses involved. The primary mechanisms were firstly the excited-state intramolecular proton transfer (i.e. phototautomerization), which generated the imidic acid phototautomer observed as [M-H](-) quasimolecular ion at m/z 314.0070 in the high-performance liquid chromatography-electrospray ionization-time-of-flight mass spectrometry in the negative mode. Secondly, the photoinduced α-cleavage with the loss of a carbonyl group occurred (i...
January 1, 2017: Antiviral Chemistry & Chemotherapy
Chidambar Kulkarni, Peter A Korevaar, Karteek K Bejagam, Anja R A Palmans, E W Meijer, Subi J George
Control over the helical organization of synthetic supramolecular systems is intensively pursued to manifest chirality in a wide range of applications ranging from electron spin filters to artificial enzymes. Typically, switching the helicity of supramolecular assemblies involves external stimuli or kinetic traps. However, efforts to achieve helix reversal under thermodynamic control and understanding the phenomena at a molecular level are scarce. Here we present a unique example of helix reversal (stereomutation) under thermodynamic control in the self-assembly of coronene bisimide (CBI-35CH) which has a 3,5-dialkoxy substitution on imide phenyl groups leading to "molecular pockets" in the assembly...
September 11, 2017: Journal of the American Chemical Society
Jun Zhou, Yanhua Lei, Chenghai Ma, Wenhua Lv, Na Li, Ying Wang, Hu Xu, Zhigang Zou
A two-dimensional imide-based conjugated polymer with a preferred (001) orientation was constructed by solvent-induced assembly. A high performance of 1640 μmol h(-1) g(-1) for solar-driven photocatalytic hydrogen evolution and an excellent stability were achieved due to tunnelling charge transport between the neighbouring molecular sheets.
September 11, 2017: Chemical Communications: Chem Comm
Rukiya Matsidik, Alessandro Luzio, Özge Askin, Daniele Fazzi, Alessandro Sepe, Ullrich Steiner, Hartmut Komber, Mario Caironi, Michael Sommer
The synthesis, characterization, and charge transport performance of novel copolymers PNDIFu2 made from alternating naphthalene diimide (NDI) and bifuran (Fu2) units are reported. Usage of potentially biomass-derived Fu2 as alternating repeat unit enables flattened polymer backbones due to reduced steric interactions between the imide oxygens and Fu2 units, as seen by density functional theory (DFT) calculations and UV-vis spectroscopy. Aggregation of PNDIFu2 in solution is enhanced if compared to the analogous NDI-bithiophene (T2) copolymers PNDIT2, occurring in all solvents and temperatures probed...
July 11, 2017: Chemistry of Materials: a Publication of the American Chemical Society
Ines Otero, Luiz Fernando Lepre, Alain Dequidt, Pascale Husson, Margarida Costa Gomes
The effect of the addition of a third ion to the ionic liquid 1-butyl-3-methylimidazolium acetate, [C4C1Im][OAc], was studied through the measurement of the enthalpy of mixing and of the excess molar volume of its mixtures with 1-butyl-3-methylimidazolium trifluoroacetate, [C4C1Im][CF3CO2], 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C4C1Im][NTf2], and tetrabutylphosphonium acetate, [P4444][OAc]. Negative enthalpies of mixing (mixH < 0) and positive excess molar volumes (VE > 0) were observed in all cases...
September 11, 2017: Journal of Physical Chemistry. B
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