89486-38-4Relevant academic research and scientific papers
'AND'-based fluorescence scaffold for the detection of ROS/RNS and a second analyte
Odyniec, Maria L.,Sedgwick, Adam C.,Swan, Alexander H.,Weber, Maria,Tang, T. M. Simon,Gardiner, Jordan E.,Zhang, Miao,Jiang, Yun-Bao,Kociok-Kohn, Gabriele,Elmes, Robert B. P.,Bull, Steven D.,He, Xiao-Peng,James, Tony D.
supporting information, p. 8466 - 8469 (2018/08/04)
Traditionally, fluorescence probes have focused on the detection of a single biomarker for a specific process. In this work, we set out to develop a number of fluorescence probes that enable the detection of a chosen analyte in the presence of reactive oxygen/nitrogen species (ROS/RNS). These fluorescence probes when activated result in the formation of the highly fluorescent pink dye, resorufin. Therefore, we have labelled these fluorescent probes as -Pinkments'. Our first -Pinkment' was shown to detect biologically relevant concentrations of ONOO- and have an excellent selectivity against other ROS/RNS. Pinkment-OH was developed to provide a core unit which could be easily functionalised to produce a range of -AND' based fluorescence probes for the detection of ROS/RNS and a second analyte. For proof of concept, we synthesised Pinkment-OTBS and Pinkment-OAc. These -AND'-based probes were successfully shown to detect ROS/RNS and F- or esterase, respectively.
Pd-Catalyzed double N-arylation of primary amines to synthesize phenoxazines and phenothiazines
Zhang, Lu,Huang, Xin,Zhen, Shan,Zhao, Jing,Li, Heng,Yuan, Bingxin,Yang, Guanyu
, p. 6306 - 6309 (2017/08/10)
An efficient and versatile Pd-catalyzed tandem C-N bond formation between aryl halides and primary amines is developed. The transformation allows a one-pot synthesis of phenoxazine and phenothiazine derivatives with a broad range of substitution patterns from readily available precursors.
N-substituted phenoxazine and acridone derivatives: Structure-activity relationships of potent P2X4 receptor antagonists
Hernandez-Olmos, Victor,Abdelrahman, Aliaa,El-Tayeb, Ali,Freudendahl, Diana,Weinhausen, Stephanie,Müller, Christa E.
supporting information, p. 9576 - 9588 (2013/01/16)
P2X4 receptor antagonists have potential as drugs for the treatment of neuropathic pain and neurodegenerative diseases. In the present study the discovery of phenoxazine derivatives as potent P2X4 antagonists is described. N-Substituted phenoxazine and related acridone and benzoxazine derivatives were synthesized and optimized with regard to their potency to inhibit ATP-induced calcium influx in 1321N1 astrocytoma cells stably transfected with the human P2X4 receptor. In addition, species selectivity (rat, mouse, human) and receptor subtype selectivity (versus P2X1,2,3,7) were investigated. The most potent P2X4 antagonist of the present series was N-(benzyloxycarbonyl)phenoxazine (26, PSB-12054) with an IC50 of 0.189 μM and good selectivity versus the other human P2X receptor subtypes. N-(p-Methylphenylsulfonyl)phenoxazine (21, PSB-12062) was identified as a selective P2X4 antagonist that was equally potent in all three species (IC50: 0.928-1.76 μM). The compounds showed an allosteric mechanism of action. The present study represents the first structure-activity relationship analysis of P2X4 antagonists.
SN2 Reactions of Nitranions with Benzyl Chlorides
Bordwell, Frederick G.,Hughes, David L.
, p. 3234 - 3240 (2007/10/02)
The rates of SN2 reactions of 19 nitranions with PhCH2Cl and 9 nitranions with m-CF3C6H4CH2Cl were measured in Me2SO at 25 deg C.Bronsted plots of log k vs. pKHA for reactions of anion families derived from carbazoles, phenothiazines, and diphenylamines with PhCH2Cl are linear with slopes of 0.32-0.33.Extension of the carbazole and phenothiazine family lines, which are collinear, provided a reference line by which nucleophilicities of other nitranions could be assessed at constant basicity.Nitranions of varied structural types were found to have remarkably similar nucleophilicities when compared at the same basicities.Steric effects caused rates of reactions of ArAr'N(1-) ions and acetanilide ion to be retarded slightly and that of benzanilide ion to be retarded appreciably.Evidence is presented to show that nitranions, like carbanions, utilize the electron pair in a p orbital for bonding to an electrophile whereas pyridines utilize a nonbonded electron pair.Comparisons with literature data for neutral nitrigen nucleophiles, such as n-BuNH2 and PhNH2, indicate that they are 10-100 times more reactive than nitranion nucleophiles of comparable basicity.The order of nucleophilicities toward PhCH2Cl of anion families with different donor atoms when compared at the same basicity was found to be the following: 9-methylfluoredine ion family (25) > 2-naphthoxide ion family (3) > carbazole ion family (1.0).The results show that basicity is the primary factor in controlling nucleophilicities of nitranions, carbanions, and oxanions of diverse structural types in SN2 reactions.Donor atom, solvation, and steric effects generally play a secondary role.
