Mild and regioselective iodination of electron-rich aromatics with N -iodosuccinimide and catalytic trifluoroacetic acid

Castanet, Anne‐Sophie; Colobert, Françoise; Broutin, Pierre-Emmanuel

doi:10.1016/s0040-4039(02)01010-9

Cited by 153 publications

(128 citation statements)

References 14 publications

Supporting

Mentioning

124

Contrasting

Order By: Relevance

“…The residue was purified by silica gel column chromatography using dichloromethane as eluent to give the desired 4-iodo-1,2-dimethoxybenzene 8 in excellent yield (1.97 g, 95%). This compound showed spectroscopic and analytical data identical to one previously reported [37].…”

Section: Synthesis Of 2-methyl-4h-chromen-4-ones (5a-5c 6)supporting

confidence: 82%

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Proença

Albuquerque

Ribeiro

et al. 2016

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

a b s t r a c tChromones and xanthones are oxygen-containing heterocyclic compounds acknowledged by their antioxidant properties. In an effort to develop novel agents with improved activity, a series of compounds belonging to these chemical classes were prepared. Their syntheses involve the condensation of appropriate 2-methyl-4H-chromen-4-ones, obtained via Baker-Venkataraman rearrangement, with (E)-3-(3,4-dimethoxyphenyl)acrylaldehyde to provide the corresponding 2-[(1E,3E)-4-(3,4-dimethoxyphenyl)buta-1,3-dien-1-yl]-4H-chromen-4-ones. Subsequent electrocyclization and oxidation of these compounds led to the synthesis of 1-aryl-9H-xanthen-9-ones. After cleavage of the protecting groups, hydroxylated chromones and xanthones were assessed as scavenging agents against both reactive oxygen species (ROS) [superoxide radical (O 2 -), hydrogen peroxide (H 2 O 2 ), hypochlorous acid (HOCl), singlet oxygen ( 1 O 2 ), and peroxyl radical (ROO )] and reactive nitrogen species (RNS) [nitric oxide ( NO) and peroxynitrite anion (ONOO À )]. Generally, all the tested new hydroxylated chromones and xanthones exhibited scavenger effects dependent on the concentration, with IC 50 values found in the micromolar range. Some of them were shown to have improved scavenging activity when compared with previously reported analogues, allowing the inference of preliminary conclusions on the structure eactivity relationship.

show abstract

Section: Synthesis Of 2-methyl-4h-chromen-4-ones (5a-5c 6)supporting

confidence: 82%

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Proença

Albuquerque

Ribeiro

et al. 2016

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…To overcome these problems we developed a strategy based on the aromatic iodination of blebbistatin followed by a halogen azide exchange step (17)(18)(19)(20)(21)(22). Iodination of blebbistatin was performed using N-iodosuccinimide and was catalyzed by the super acid boron trifluoride dihydrate, which was also the main solvent of the reaction (Fig.…”

Section: Resultsmentioning

confidence: 99%

Azidoblebbistatin, a photoreactive myosin inhibitor

Képiró¹,

Várkuti²,

Bodor³

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

View full text Add to dashboard Cite

Photoreactive compounds are important tools in life sciences that allow precisely timed covalent crosslinking of ligands and targets. Using a unique technique we have synthesized azidoblebbistatin, which is a derivative of blebbistatin, the most widely used myosin inhibitor. Without UV irradiation azidoblebbistatin exhibits identical inhibitory properties to those of blebbistatin. Using UV irradiation, azidoblebbistatin can be covalently crosslinked to myosin, which greatly enhances its in vitro and in vivo effectiveness. Photo-crosslinking also eliminates limitations associated with the relatively low myosin affinity and water solubility of blebbistatin. The wavelength used for photo-crosslinking is not toxic for cells and tissues, which confers a great advantage in in vivo tests. Because the crosslink results in an irreversible association of the inhibitor to myosin and the irradiation eliminates the residual activity of unbound inhibitor molecules, azidoblebbistatin has a great potential to become a highly effective tool in both structural studies of actomyosin contractility and the investigation of cellular and physiological functions of myosin II. We used azidoblebbistatin to identify previously unknown low-affinity targets of the inhibitor (EC 50 ≥ 50 μM) in Dictyostelium discoideum, while the strongest interactant was found to be myosin II (EC 50 = 5 μM). Our results demonstrate that azidoblebbistatin, and potentially other azidated drugs, can become highly useful tools for the identification of strong-and weak-binding cellular targets and the determination of the apparent binding affinities in in vivo conditions. interactom profile | azidation | photoactivation V arious biological processes, including muscle contraction, cell migration, differentiation, and cytokinesis require the activity of myosin II, a class of actin-based ATP-driven motor proteins. Cell-permeable small molecules that can perturb myosin functions have greatly aided the dissection and understanding of molecular processes underlying the above phenomena. Myosin II inhibitors described to date include 2,3-butanedione monoxime (BDM) (1, 2), N-benzyl-p-toluenesulphonamide (BTS) (3), and blebbistatin (4-6). As BDM has turned out to have a broad effect on many other proteins (7) and the inhibitory effect of BTS is limited to fast skeletal muscle myosin, until now blebbistatin has been the only potent tool for specific blocking of myosin II-dependent processes in various species and cell types. Recent data have shown that halogenated pseudilins also have nonspecific inhibitory effects on myosin II isoforms (8-10).In vitro, blebbistatin inhibits vertebrate striated muscle and nonmuscle myosin II isoforms as well as Dictyostelium discoideum (Dd) myosin II by about 95%, with an IC 50 of 0.5-5 μM (11). Vertebrate smooth muscle and Acanthamoeba myosin II are incompletely inhibited even at high blebbistatin concentrations. In vivo experiments performed with Dd showed that the effective inhibition of myosin II-dependent processes, including growth in...

show abstract

“…3 The reaction is para-directed. Iodine trifluoroacetate is pointed out as the active species for iodination.…”

Section: Abstractsmentioning

confidence: 99%

N-Iodosuccinimide (NIS)

Sniady¹

2006

Synlett

View full text Add to dashboard Cite

show abstract

Mild and regioselective iodination of electron-rich aromatics with N -iodosuccinimide and catalytic trifluoroacetic acid

Cited by 153 publications

References 14 publications

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Novel chromone and xanthone derivatives: Synthesis and ROS/RNS scavenging activities

Azidoblebbistatin, a photoreactive myosin inhibitor

N-Iodosuccinimide (NIS)

Contact Info

Product

Resources

About