4010-19-9Relevant articles and documents
Novel Bifunctionalization of Activated Methylene: Base-Promoted Trifluoromethylthiolation of β-Diketones with Trifluoromethanesulfinyl Chloride
Sun, Dong-Wei,Jiang, Min,Liu, Jin-Tao
supporting information, p. 10797 - 10802 (2019/07/03)
A novel bifunctionalization of activated methylene was achieved successfully through the base-promoted trifluoromethylthiolation of β-diketones or β-ketoesters with trifluoromethanesulfinyl chloride. A series of α-trifluoromethylthiolated α-chloro-β-diketones and α-chloro-β-ketoesters were obtained in moderate to good yields under mild conditions. When β-diketones containing a phenyl group with a hydroxyl or amino substituent at the ortho position were used as substrates, intramolecular trifluoromethylthiolation/cyclization reaction took place to give the corresponding cyclic products. Furthermore, the protocol could be extended to perfluoroalkylthiolation with the sodium perfluoroalkanesulfinate/POCl3 system. On the basis of experimental results, plausible mechanisms are proposed.
Rational design for multicolor flavone-based fluorophores with aggregation-induced emission enhancement characteristics and applications in mitochondria-imaging
Liu, Liyan,Lei, Yaohui,Zhang, Jianhui,Li, Na,Zhang, Fan,Wang, Huaqiao,He, Feng
, (2018/09/14)
Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted more attention in recent years. In order to realise more valuable applications, the different kinds of AIEE molecules are in serious need of further development. Therefore, a novel flavone-based AIEE system derived from restriction of intramolecular rotation (RIR) was designed and synthesized in this work. The results revealed that six of the compounds showed typical AIEE characteristics, with fluorescence emissions from purple, blue, cyan to green, tunable by changing substituent groups. This flavone-based AIEE system has never been reported before. The AIEE characteristics were investigated by optical spectroscopy, fluorescence photographs, scanning electron microscopy (SEM), fluorescence quantum yields (φF) and fluorescence lifetime in the CH3OH/H2O mixed solution. Moreover, benefiting from the simple structures and small molecular weight, they could permeate cells faster than current high-molecular-weight AIEE molecules. Furthermore, to examine possible biomedical applications, fluorescence imaging in living A549 lung cells and cell viabilities were examined, and the results displayed that these fluorophores showed good cellular uptake and low cytotoxicity within the experimental concentration range. In addition, these AIEE compounds possessed excellent specificity for mitochondrial targeting and mitochondrial morphological change tracking, besides, they displayed superior photostability, which indicated they are potential candidates for mitochondrial imaging.
Synthesis of novel fused chromone-pyrimidine hybrids and 2,4,5-trisubstituted pyrimidine derivatives via ANRORC rearrangement
Sambaiah,Raghavulu,Shiva Kumar,Yennam, Satyanarayana,Behera, Manoranjan
supporting information, p. 10020 - 10026 (2017/09/18)
A facile and versatile procedure for the synthesis of functionalized novel 2,5-diphenyl-5H-chromeno[4,3-d]pyrimidin-5-ol and (2,4-diphenylpyrimidin-5-yl) (2-hydroxyphenyl) methanone has been described. The key step in the synthesis involves the ANRORC rea
Intervention in cyclophosphamide induced oxidative stress and DNA damage by a flavonyl-thiazolidinedione based organoselenocyanate and evaluation of its efficacy during adjuvant therapy in tumor bearing mice
Roy, Somnath Singha,Chakraborty, Pramita,Bhattacharya, Sudin
, p. 195 - 209 (2014/01/23)
A novel flavonyl-thiazolidinedione based organoselenocyanate compound was synthesized and established as nontoxic at the doses of 2.5 and 5 mg/kg b.w. in mice. Oral administration of the compound in combination with cyclophosphamide (CP) resulted in an im
Directing group assisted copper-catalyzed chemoselective O-aroylation of phenols and enols using alkylbenzenes
Rout, Saroj Kumar,Guin, Srimanta,Banerjee, Arghya,Khatun, Nilufa,Gogoi, Anupal,Patel, Bhisma K.
supporting information, p. 4106 - 4109 (2013/09/12)
By using alkylbenzenes as aroyl surrogates, copper(II) catalyzed chemoselective O-aroylations of 1,3-dicarbonyl compounds and phenolic-OH ortho to carbonyl (-CHO,-COR) groups have been achieved. A dual mechanism operating in tandem for these transformations has been supported by a crossover experiment.
A new synthesis of flavones and pyranoflavone by intramolecular photochemical Wittig reaction in water
Das, Jhantu,Ghosh, Somnath
supporting information; experimental part, p. 7189 - 7194 (2012/01/05)
A new synthetic approach toward the synthesis of flavones and pyranoflavone has been developed by light induced intramolecular photochemical Wittig reaction in water onto aryloxycarbonyl groups and suitably substituted phosphonium bromides sans any phase transfer catalyst or promoter.
Synthesis and properties of molecular probes for the rescue site on mutant cystic fibrosis transmembrane conductance regulator
Alkhouri, Bashar,Denning, Robert A.,Chiaw, Patrick Kim,Eckford, Paul D.W.,Yu, Wilson,Li, Canhui,Bogojeski, Jovanka J.,Bear, Christine E.,Viirre, Russell D.
experimental part, p. 8693 - 8701 (2012/03/09)
Cystic fibrosis is a genetic disease caused by mutations in the gene for the cystic fibrosis transmembrane conductance regulator (CFTR) protein. In vitro experiments have demonstrated that 4-methyl-2-(5-phenyl-1H-pyrazol-3-yl)phenol (VRT-532, 1) is able t
New synthesis of 3-bromoflavones via bromination of 1-(2-hydroxyphenyl)-3- arylpropane-1,3-dione by CuBr2, and conversion into 3-aminoflavones
Miyake, Hideyoshi,Nishino, Shouko,Nishimura, Akinori,Sasaki, Mitsura
, p. 522 - 523 (2008/02/10)
A new synthesis of 3-bromoflavones from 1-(2-hydroxyphenyl)-3-arylpropane- 1,3-dione using CuBr2 is described. The usefulness of 3-bromoflavone as a precursor of 3-aminoflavone is also described. Copyright
Fast synthesis of some flavones under microwave irradiation
Mumtazuddin
, p. 835 - 837 (2007/10/03)
Reactions under microwave irradiation occur under solvent free conditions. Such reactions occur in much shorter time than the usual ones. Fast synthesis of flavone from o-hydroxyacetophenone has been achieved in three steps under microwave irradiation.
Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABAA receptor
Kahnberg, Pia,Lager, Erik,Rosenberg, Celia,Schougaard, Jette,Camet, Linda,Sterner, Olov,Nielsen, Elsebet ?stergaard,Nielsen, Mogens,Liljefors, Tommy
, p. 4188 - 4201 (2007/10/03)
To further develop and evaluate a pharmacophore model previously proposed by Cook and co-workers (Drug Des. Discovery 1995, 12, 193-248) for ligands binding to the benzodiazepine site of the GABAA receptor, 40 new flavone derivatives have been synthesized and their affinities for the benzodiazepine site have been determined. Two new regions of steric repulsive interactions between ligand and receptor have been characterized, and the receptor region in the vicinity of 6- and 3′-substituents has been mapped out. 2′-Hydroxy substitution is shown to give a significant increase in affinity, which is interpreted in terms of a novel hydrogen bond interaction with the previously proposed hydrogen bond-accepting site A2. On the basis of the results of these studies and the refined pharmacophore model, 5′-bromo-2′-hydroxy-6-methylflavone, the highest affinity flavone derivative reported so far (Ki = 0.9 nM), was successfully designed. A comparison of the pharmacophore model with a recently proposed alternative model (Marder; et al. Bioorg. Med. Chem., 2001, 9, 323-335) has been made.
