65548-54-1Relevant articles and documents
Diversity-oriented synthesis of pyrazoles derivatives from flavones and isoflavones leads to the discovery of promising reversal agents of fluconazole resistance in Candida albicans
Cui, Chang-Yi,Liu, Jun,Zheng, Hong-Bo,Jin, Xue-Yang,Zhao, Xiao-Yu,Chang, Wen-Qiang,Sun, Bin,Lou, Hong-Xiang
supporting information, p. 1545 - 1549 (2018/04/02)
Diversity-oriented synthesis of derivatives of natural products is an important approach for the discovery of novel drugs. In this paper, a series of novel 3,4-diaryl-1H-pyrazoles and 3,5-diaryl-1H-pyrazoles derivatives were synthesized through the one-po
Towards tropomyosin-related kinase B (TrkB) receptor ligands for brain imaging with PET: Radiosynthesis and evaluation of 2-(4-[18F] fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one and 2-(4-([N-methyl- 11C]-dimethylamino)phenyl)-7,8-dihydroxy-4H-chromen-4-one
Bernard-Gauthier, Vadim,Boudjemeline, Mehdi,Rosa-Neto, Pedro,Thiel, Alexander,Schirrmacher, Ralf
, p. 7816 - 7829 (2014/01/06)
The interaction of tropomyosin-related kinase B (TrkB) with the cognate ligand brain-derived neurotrophic factor (BDNF) mediates fundamental pathways in the development of the nervous system. TrkB signaling alterations are linked to numerous neurodegenerative diseases and conditions. Herein we report the synthesis, biological evaluation and radiosynthesis of the first TrkB radioligands based on the recently identified 7,8-dihydroxyflavone chemotype. 2-(4-[18F]fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one ([ 18F]10b) was synthesized in high radiochemical yields via an efficient SNAr radiofluorination involving a para-Michael acceptor substituted aryl followed by BBr3-promoted double demethylation. Selective N-[11C]methylation afforded 2-(4-([N-methyl- 11C]-dimethylamino)phenyl)-7,8-dihydroxy-4H-chromen-4-one ([ 11C]10c) from the fully deprotected catechol-bearing normethyl precursor 13 with [11C]MeOTf. In vitro autoradiography of [ 18F]10b with transverse rat brain sections revealed high specific binding in the cortex, striatum, hippocampus and thalamus in accordance with expected TrkB distribution. Blockade experiments with both 7,8-dihydroxyflavone (1a) and TrkB cognate ligand, BDNF, led to decreases of 80% and 85% of radioligand binding strongly supporting the hypothesis that 7,8- dihydroxyflavones exert their effect on TrkB phosphorylation via direct TrkB extracellular domain (ECD) binding. Positron emission tomography (PET) studies revealed that [18F]10b and [11C]10c brain uptake is minimal and that they are rapidly eliminated from the plasma (effective plasma half-life 5-10 min) via hepatic secretion. Nevertheless, the high specific binding and TrkB specificity derived from in vitro experiments suggests that the 7,8-disubstituted flavone chemotype represents a promising scaffold for the development of TrkB radiotracers for PET.
Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)
Barontini, Maurizio,Bernini, Roberta,Crisante, Fernanda,Fabrizi, Giancarlo
experimental part, p. 6047 - 6053 (2010/09/11)
2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 °C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described.
