52355-50-7Relevant academic research and scientific papers
An inexpensive fluorescent labeling protocol for bioactive natural products utilizing Cu(I)-catalyzed Huisgen reaction
Zhang, Yan-Hong,Gao, Zheng-Xi,Zhong, Chun-Long,Zhou, Hai-Bin,Chen, Lei,Wu, Wen-Min,Peng, Xin-Jun,Yao, Zhu-Jun
, p. 6813 - 6821 (2007)
Labeling of bioactive small molecules with organic dyes for various applications in cell biology has been emerging as an attractive research field. Using an easily prepared and inexpensive fluorescein derivative 1 and a Cu(I)-catalyzed Huisgen reaction, a
Novel linear polymers bearing thiosialosides as pendant-type epitopes for influenza neuraminidase inhibitors
Matsuoka, Koji,Takita, Chiharu,Koyama, Tetsuo,Miyamoto, Daisei,Yingsakmongkon, Sangchai,Hidari, Kazuya I.P.J.,Jampangern, Wipawee,Suzuki, Takashi,Suzuki, Yasuo,Hatano, Ken,Terunuma, Daiyo
, p. 3826 - 3830 (2007)
A conventional synthesis of α-thioglycoside of sialic acid as a glycomonomer was accomplished. Radical copolymerization of the glycomonomer with vinyl acetate proceeded smoothly to afford a new class of glycopolymers having thiosialoside residues, in which all protection was removed by a combination of transesterification and saponification to provide a water-soluble thiosialoside cluster. The results of a preliminary study on biological responses against influenza virus neuraminidases using the thiosialoside polymer as a candidate for a neuraminidase inhibitor showed that the glycopolymer has potent inhibitory activity against the neuraminidases.
Diethylzinc-Mediated Radical 1,2-Addition of Alkenes and Alkynes
Li, Xin,He, Songtao,Song, Qiuling
supporting information, p. 2994 - 2999 (2021/05/04)
A novel diethylzinc-mediated radical 1,2-addition of perfluoroalkyl iodides to unactivated alkenes and alkynes is presented, which demonstrates a novel way to generate an ethyl difluoroacetate radical. This method is highly efficient and gives full conversions of the substrates, high yields of the products, and negligible byproducts and requires no column chromatography purifications. The mild conditions enable this protocol to exhibit excellent functional group compatibility.
Heck functionalization of an asymmetric aza-BODIPY core: synthesis of far-red infrared probes for bioimaging applications
Parisotto, Stefano,Lace, Beatrice,Artuso, Emma,Lombardi, Chiara,Deagostino, Annamaria,Scudu, Roberto,Garino, Claudio,Medana, Claudio,Prandi, Cristina
supporting information, p. 884 - 893 (2017/02/05)
As part of our ongoing work on the synthesis of a new class of plant hormones named Strigolactones (SLs) and their analogues, we became interested in tracing bioactive molecules with red emitting BODIPY fluorophores in order to unravel signaling and distribution of SLs in plants. In this paper we report on an unprecedented Heck functionalization of azadipyrromethenes (aza-DIPY) which allows for the introduction of suitable functional groups to convert aza-BODIPY in bioconjugate complexes useful for untangling biological processes.
Photoresponsive amphiphiles based on azobenzene-dendritic glycerol conjugates show switchable transport behavior
Koerdel, Christian,Popeney, Chris S.,Haag, Rainer
supporting information; experimental part, p. 6584 - 6586 (2011/06/27)
The synthesis and aggregation behavior of photo-switchable, nonionic dendritic amphiphiles was investigated with regard to transport and release of guest molecules. The correlation between the critical micelle concentration and the switching ability is shown.
Flexible and enantioselective access to jaspine B and biologically active chain-modified analogues thereof
Salma, Yahya,Ballereau, Stephanietlse,Maaliki, Carine,Ladeira, Sonia,Andrieu-Abadie, Nathalie,Genisson, Yves
experimental part, p. 3227 - 3243 (2010/08/21)
Whereas the all-cis tetrahydrofuran framework of the cytotoxic anhydrophytosphingosine jaspine B is considered as a relevant pharmacophore, little is known about the influence of the aliphatic chain of this amphiphilic molecule on its activity. We develop
Cyclic tetramer of a metalloporphyrin based on a quadruple hydrogen bond
Ohkawa, Haruki,Takayama, Akihiro,Nakajima, Satoshi,Nishide, Hiroyuki
, p. 2225 - 2228 (2007/10/03)
This paper describes the selective formation of a cyclic tetramer from a readily synthesized metalloporphyrin with two self-complementary quadruple hydrogen-bonding units. The extremely strong quadruple hydrogen-bonding unit, 2-ureido-4[1H]-pyrimidinone,
Covalently attached monolayers on crystalline hydrogen-terminated silicon: Extremely mild attachment by visible light
Sun, Qiao-Yu,De Smet, Louis C. P. M.,Van Lagen, Barend,Giesbers, Marcel,Thuene, Peter C.,Van Engelenburg, Johan,De Wolf, Frits A.,Zuilhof, Han,Sudhoelter, Ernst J. R.
, p. 2514 - 2523 (2007/10/03)
A very mild method was developed for the attachment of high-quality organic monolayers on crystalline silicon surfaces. By using visible light sources, from 447 to 658 nm, a variety of 1-alkenes and 1-alkynes were attached to hydrogen-terminated Si(IOO) and Si(111) surfaces at room temperature. The presence and the quality of the monolayers were evaluated by static water contact angles, X-ray photoelectron spectroscopy, and IR spectroscopy. Monolayers prepared by thermal, UV light, or visible light initiation were compared. Additionally, the ability of infrared reflection-absorption spectroscopy to study organic monolayers on silicon was explored. A reaction mechanism is discussed on the basis of investigations of the reaction behavior of 1-alkenes with silicon wafers with varying types and levels of doping. Finally, a series of mixed monolayers derived from the mixed solutions of a 1-alkene and an ω-fluoro-1-alkene were investigated to reveal that the composition of the mixed monolayers was directly proportional to the molar ratio of the two compounds in the solutions.
Macrocyclic inhibitors for peptide deformylase: A structure-activity relationship study of the ring size
Hu, Xubo,Nguyen, Kiet T.,Jiang, Vernon C.,Lofland, Denene,Moser, Heinz E.,Pei, Dehua
, p. 4941 - 4949 (2007/10/03)
Peptide deformylase (PDF) catalyzes the removal of the N-terminal formyl group from newly synthesized polypeptides in eubacteria. Its essential role in bacterial cells but not in mammalian cells makes it an attractive target for antibacterial drug design. We have previously reported an N-formylhydroxylamine- based, metal-chelating macrocyclic PDF inhibitor, in which the P 1′ and P3′ side chains are covalently joined. In this work, we have carried out a structure-activity relationship study on the size of the macrocycle and found that 15-17-membered macrocycles are optimal for binding to the PDF active site. Unlike the acyclic compounds, which are simple competitive inhibitors, the cyclic compounds all act as slow-binding inhibitors. As compared to their acyclic counterparts, the cyclic inhibitors displayed 20-50-fold higher potency against the PDF active site (K I* as low as 70 pM), improved selectivity toward PDF, and improved the metabolic stability in rat plasma. Some of the macrocyclic inhibitors had potent, broad spectrum antibacterial activity against clinically significant Gram-positive and Gram-negative pathogens. These results suggest that the macrocyclic scaffold provides an excellent lead for the development of a new class of antibiotics.
Evaluation of exo-endo ratios in the halolactonization of ω-unsaturated acids
Roux,Paugam,Rousseau
, p. 4304 - 4310 (2007/10/03)
The reaction of 2-(ω-alkenyl)benzoic acids with bis(collidine)iodine and bis(collidine)bromine hexafluorophosphate was examined. Except with 2-but-3-enylbenzoic acid, for which only the exo lactone was obtained, for the other acids a mixture of exo-endo lactones was always obtained. The proportion of endo lactone was important for the acid chain length of 11 carbons (formation of a 12-membered ring endo lactone) and for the acid chain lengths higher than 14 carbons. The formation of the endo lactones was explained, on the base of molecular calculations, by competition between electronic and steric effects. These latter were developed by transannular interactions (for the acid chain lengths 8-11) and/or the conformations adopted by the chains (for the acid chain lengths ≥ 14,) which disfavored the formation of the exo lactones. The larger proportion of endo lactones observed with the bromo reagent compared to the iodo reagent seemed due to electronic factors.
