27318-31-6Relevant academic research and scientific papers
Strong electron acceptor properties of 3'(Pentafluorophenyl)isoxazolo[4',5':1,2][60]fullerene derivatives
Irngartinger, Hermann,Escher, Thomas
, p. 10753 - 10760 (1999)
Investigations on the synthesis and electrochemical behaviour of a new class of acceptor substituted isoxazolofullerenes is described. The influence of distance and orientation of pentafluorophenyl substituents on cyclic voltammetry is discussed. The stro
Discovery, synthesis, and biological evaluation of a novel group of selective inhibitors of filoviral entry
Yermolina, Maria V.,Wang, Jizhen,Caffrey, Michael,Rong, Lijun L.,Wardrop, Duncan J.
experimental part, p. 765 - 781 (2011/04/15)
Herein, we report the development of an antifiloviral screening system, based on a pseudotyping strategy, and its application in the discovery of a novel group of small molecules that selectively inhibit the Ebola and Marburg glycoprotein (GP)-mediated infection of human cells. Using Ebola Zaire GP-pseudotyped HIV particles bearing a luciferase reporter gene and 293T cells, a library of 237 small molecules was screened for inhibition of GP-mediated viral entry. From this assay, lead compound 8a was identified as a selective inhibitor of filoviral entry with an IC50 of 30 μM. To analyze functional group requirements for efficacy, a structure-activity relationship analysis of this 3,5-disubstituted isoxazole was then conducted with 56 isoxazole and triazole derivatives prepared using "click" chemistry. This study revealed that while the isoxazole ring can be replaced by a triazole system, the 5-(diethylamino)acetamido substituent found in 8a is required for inhibition of viral-cell entry. Variation of the 3-aryl substituent provided a number of more potent antiviral agents with IC50 values ranging to 2.5 μM. Lead compound 8a and three of its derivatives were also found to block the Marburg glycoprotein (GP)-mediated infection of human cells.
One-pot copper(I)-catalyzed synthesis of 3,5-disubstituted isoxazoles
Hansen, Trond V.,Wu, Peng,Fokin, Valery V.
, p. 7761 - 7764 (2007/10/03)
3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional
STEREOCHEMISTRY OF IMINOXY RADICALS
Alberti, Angelo,Barbaro, Gaetano,Battaglia, Arturo,Guerra, Maurizio,Bernardi, Fernando,et al.
, p. 742 - 750 (2007/10/02)
Iminoxy radicals of general structure Ar-C(X)=N-O, where X=H, CH2OH, n-Bu, t-Bu, SiEt3, SiPh3, GePh3, SnMe3, SnBu3, SnPh3, SMe, SBu, SPh, Cl and Br, have been photolytically generated from the parent oximino compounds or from aromatic nitrile N-oxides in an aprotic solvent.Two configurational isomers, interconvertible in solution, have been detected by electron spin resonance spectroscopy for the majority of these radicals.The preferred geometry of iminoxyls derived from ortho-unsubstituted benzaldoximes is that which places the aryl ring and the oxygen atom on the same side of the C=N double bond (anti).Substitution of the azomethine proton leads to a stabilization of the syn configuration, the effect being larger the greater the atomic number of the leading atom of the substituent group.The relative stability of the syn isomer is also increased by substitution of the aromatic ortho protons.INDO calculations have been carried out on several model systems in order to rationalize the experimental results.The effects responsible for the configurational preference of the different terms of this series of radicals are discussed in terms of a perturbation molecular orbital (PMO) approach.
