122590-76-5Relevant academic research and scientific papers
FUNCTIONALIZED PERFLUOROPHENYL AZIDES. NEW REAGENTS FOR PHOTOAFFINITY LABELING
Keana, John W.,Cai,Sui Xiong
, p. 151 - 154 (1989)
Several substituted perfluorophenyl azides capable of attachement to other molecules by an acylation reaction were synthesized for use as photoaffinity labeling reagents.
Synthesis of nitrophenyl and fluorophenyl azides and diazides by SNAr under phase-transfer or microwave irradiation: Fast and mild methodologies to prepare photoaffinity labeling, crosslinking, and click chemistry reagents
Leyva, Elisa,Aguilar, Johana,González-Balderas, Regina M.,Vega-Rodríguez, Sarai,Loredo-Carrillo, Silvia E.
, (2020/12/01)
Two fast and mild methodologies to prepare nitrophenyl and fluorophenyl azides are presented. These aryl azides are extensively used as crosslinking, photoaffinity labeling, and click chemistry reagents. Substituted aryl azides are prepared by performing a SNAr substitution on halogenated benzenes with a phase-transfer catalyst (PTC) such as tetraethylammonium tetrafluoroborate (TEATFB), the reaction proceeds in several hours under rather mild temperatures (25°C to 70°C). Furthermore, aryl azides are also prepared within minutes under microwave irradiation at slightly higher temperatures (50°C to 70°C). These procedures could be applied in the preparation of other aryl azides. In the case of substituted pentafluoro benzene (pF), the type of products obtained in each reaction depends on the amount of sodium azide and the strength and position of electron-withdrawing substituents (COH, COR, COOR, CN, NO2, or F). A discussion on the mechanisms and the products obtained in these SNAr reactions is presented.
Microwave-assisted synthesis of substituted fluorophenyl mono- and diazides by SNAr. A fast methodology to prepare photoaffinity labeling and crosslinking reagents
Leyva, Elisa,Leyva, Socorro,Moctezuma, Edgar,González-Balderas, Regina M.,De Loera, Denisse
, p. 164 - 169 (2013/11/19)
The reaction of sodium azide with perfluorobenzene, containing an electron-withdrawing group, under microwave irradiation results in the fast preparation of p-substituted tetrafluorophenyl monoazides. Having an excess of sodium azide and a strong electron-withdrawing group like NO2 or CN, fluorophenyl diazides are also produced upon conventional or microwave heating. A synergic effect between the amount of sodium azide and the electron-withdrawing character of the substituents is observed giving different products. A discussion on the products and reaction mechanism is presented.
Progestin 16α,17α-dioxolane ketals as molecular probes for the progesterone receptor: Synthesis, binding affinity, and photochemical evaluation
Kym,Carlson,Katzenellenbogen
, p. 1111 - 1119 (2007/10/02)
Chemical probes for steroid receptors have proven useful in providing molecular details about important hormone-receptor interactions. A series of progestin 16α,17α-dioxolane ketals of acetophenone or substituted acetophenones that bind to the progesterone receptor (PgR) with comparable or higher affinities than the natural ligand, progesterone, have been prepared and evaluated as potential in vitro and in vivo probes for the progesterone receptor. p-Azidoacetophenone ketal 6, the tetrafluoro analog 8, and the p- (benzoyl)acetophenone ketal 9 demonstrate the required combination of high relative binding affinity (RBA) (6 = 15%, 8 = 14%, 9 = 6.6%, progesterone = 13%, R5020 = 100%) and photoinactivation efficiency (6 = 80%, 8 = 77%, 9 = 29% at 30 min) required for potential photoaffinity labeling reagents for the PgR. The synthesis of azide 6 has been modified to accommodate a palladium- catalyzed tritium gas hydrogenolysis of an iodoaryl precursor in the final stage of the synthetic sequence; this procedure has been verified by hydrogenation. In addition, the progestin p-fluoroacetophenone ketal 10 was selected for preparation in fluorine-18-labeled form, on the basis of its high affinity for the PgR (RBA = 53%). Fluorine-18-labeled progestins may be evaluated as potential diagnostic imaging agents for PgR-positive breast tumors. The radiochemical syntheses and further biochemical results with the fluorine-18-labeled ketal 10 and the tritium-labeled aryl azide 6 will be presented in an accompanying paper and elsewhere.
New Reagents for Photoaffinity Labeling: Synthesis and Photolysis of Functionalized Perfluorophenyl Azides
Keana, John F. W.,Cai, Sui Xiong
, p. 3640 - 3647 (2007/10/02)
Functionalized perfluorophenyl azides (PFPA) 2-6, 8-12, 14-19, and 21-29 were synthesized, allowing the attachment of PFPA to other molecules for application as photolabels.Two biactive molecules were modified by a PFPA as potential photoaffinity labeling reagents.Photolysis of two representative members was investigated.Photolysis of azide 4 in cyclohexane gave 57 percent of CH insertion product.When photolysis was carried out in the presence of diethylamine as a trapping reagent, it gave 65 percent of NH insertion product, and no ring expansion product was found.The nitro azide 19 showed a shoulder absorption in the longer wavelength compared to azide 4.Azide 19 gave less CH insertion and more aniline products compared to azide 4 when photolyzed in toluene, suggesting that the nitro group accelerates intersystem crossing of the singlet nitrene or the singlet excited azide.Collectively, our results demonstrate that the functionalized PFPA investigated are much better in undergoing CH insertion than their nonfluorinated analogues and suggest that they may constitute an improved series of photolabeling reagents.
