29976-82-7Relevant academic research and scientific papers
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.
Rh(III)-Catalyzed Aldehydic C?H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
Xu, Guo-Dong,Huang, Kenneth L.,Huang, Zhi-Zhen
supporting information, p. 3318 - 3323 (2019/06/25)
A novel aldehydic C?H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. A plausible mechanism involving aldehydic C(sp2)?H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed. It was also found that the aldehydic C?H functionalization followed by dehydrative cyclization was able to produce flavonoids in one-pot. (Figure presented.).
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
Transition-Metal-Free Photoinduced Intramolecular Annulation of 2,3-Di(hetero)arylchromen-4-one
Han, Jie,Wang, Tao,Liang, Yong,Li, Ying,Li, Chenchen,Wang, Rui,Feng, Siqi,Zhang, Zunting
supporting information, p. 3552 - 3555 (2017/07/17)
An efficient transition-metal-free photoinduced intracyclization of 4H-chromen-4-ones in EtOH-H2O (7:1, v/v) at ambient temperature for the construction of complicated fused-ring heteroaromatics is established. The reaction proceeds smoothly without requiring any catalysts/additives.
Mild and efficient organocatalytic method for the synthesis of flavones
Stanek, Filip,Stodulski, Maciej
supporting information, p. 3841 - 3843 (2016/08/02)
A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.
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
An efficient synthesis of 3-bromoflavones under solvent free conditions using grinding technique
Jakhar, Komal,Makrandi
body text, p. 770 - 773 (2012/06/30)
Selective bromination of 1-(2-hydroxyphenyl)-3-phenylpropane- 1,3-diones has been carried out with ammonium bromide and ammonium persulphate at room temperature using grinding technique under solvent free conditions to give 2-bromo derivatives which on cyclodehydration with p-toluenesulphonic acid under grinding conditions give 3-bromoflavones. Also, flavones on bromination using above mentioned conditions give 3-bromoflavones directly.
Investigation on the substitution effects of the flavonoids as potent anticancer agents: A structure-activity relationships study
Wang, Xiao-Bing,Yang, Lei,Kong, Ling-Yi,Liu, Wei,Guo, Qing-Long
, p. 1833 - 1849,17 (2020/07/30)
Three series of flavonoid analogues substituted with different aminomethyl substitutions at C-6, C-7, and C-8 were designed and synthesized for the structure-activity relationship studies as potent anticancer agents. The prepared analogues were evaluated for their in vitro inhibitory activity against the growth of the hepatic cancer cell lines HepG2 and SMMC-7721. Structure-activity relationships indicated that not only the compounds with amino methyl groups were more active than those without the groups in the same series but also the compounds substituted by aminomethyl groups at position C-8 were more active than those at positions C-6 and C-7.
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
