67858-32-6Relevant academic research and scientific papers
Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease
Singh, Manjinder,Kaur, Maninder,Vyas, Bhawna,Silakari, Om
, p. 520 - 530 (2017/10/09)
Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit AChE AGEs formation with additional radical scavenging activity. Especially, 5m, 5b, and 5j displayed the greatest ability to inhibit AChE (IC50 = 8.0, 8.2, and 11.8 nM, respectively) and AGEs formation (IC50 = 55, 79, and 54 μM, respectively) with good antioxidant activity. Molecular docking studies explored the detailed interaction pattern with active, peripheral, and mid-gorge sites of AChE. These compounds, exhibiting such multiple pharmacological activities, can be further taken a lead for the development of potent drugs for the treatment of Alzheimer’s disease.
Synthesis and anti-trypanosoma cruzi activity of diaryldiazepines
Menezes, Jlio Csar L.,Vaz, Luana Beatriz A.,De Vieira, Paula Melo Abreu,Fonseca, Ktia Da Silva,Carneiro, Cludia Martins,Taylor, Jason G.
, p. 43 - 51 (2015/01/30)
Chagas disease is a so-called "neglected disease" and endemic to Latin America. Nifurtimox and benznidazole are drugs that have considerable efficacy in the treatment of the acute phase of the disease but cause many significant side effects. Furthermore, in the Chronic Phase its efficiency is reduced and their therapeutic effectiveness is dependent on the type of T. cruzi strain. For this reason, the present work aims to drive basic research towards the discovery of new chemical entities to treat Chagas disease. Differently substituted 5,7-diaryl-2,3-dihydro-1,4-diazepines were synthesized by cyclocondensation of substituted flavones with ethylenediamine and tested as anti-Trypanosoma cruzi candidates. Epimastigotes of the Y strain from T. cruzi were used in this study and the number of parasites was determined in a Neubauer chamber. The most potent diaryldiazepine that reduced epimastigote proliferation exhibited an IC50 value of 0.25 μM, which is significantly more active than benznidazole.
Synthesis of Flavones via Application of the Nitrile Oxide and the Stille Reactions
Gothelf, Kurt V.,Torssell, Kurt B. G.
, p. 61 - 67 (2007/10/02)
Hydroxylated and methoxylated benzaldehyde oximes have been chlorinated, dehydrohalogenated and cycloadded to tributylstannylacetylene to give 3-aryl-5-tributylstannylisoxazoles in good to excellent yields.The palladium-catalyzed coupling reaction, the so-called Stille reaction, of hindered and electron-rich 2-iodophenols and a 2-iodo-1,4-benzoquinone with 3-aryl-5-tributylstannyl-isoxazoles gave 3-aryl-5-(2-hydroxyaryl)isoxazoles in moderate to excellent yields.The coupling reaction was studied under various conditions and with various Pd(II) and Pd(0) complexes.Reduction of the 3,5-diarylisoxazoles with H2/Raney-Ni, hydrolysis and acid-catalyzed cyclisation gave flavones.The synthesis of 2-iodo-3,5-dimethoxy-1,4-benzoquinone is described.
A practical synthesis of flavones from methyl salicylate
Nagarathnam, Dhanapalan,Cushman, Mark
, p. 5071 - 5076 (2007/10/02)
A facile synthetic method has been developed for the conversion of methyl salicylate (5) into flavones 1a-i in high yields. Compound 5 on treatment with t-butyldimethylsilyl chloride (6) gave the O-silyl protected ester 7. Condensation of this ester 7 with the lithium anion generated from acetophenones 3a-i yielded the 1.3-diarylpropane-1,3-diones 8a-i, which on treatment with glacial acetic acid containing 0.5% H2SO4 for 3 h at 95-100°C provided the desired flavones 1a-i in 83-94% yields.
PHOTOACTIVABLE FLUOROPHORENES. 2. SYNTHESIS AND PHOTOACTIVATION OF FUNCTIONALIZED 3-AROYL-2-(2-FURYL)-CHROMONES
Cummings, Richard T.,DiZio, James P.,Krafft, Grant A.
, p. 69 - 72 (2007/10/02)
The synthesis and photochemistry of functionalized 3-aroyl-2-(2-furyl)-chromones 1 which are photoactivable fluorophores are described.Irradiation converts the non-fluorescent furyl chromones to highly fluorescent 1-arylfuro chromones 3.Functionality has been incorporated to permit covalent attachment, impart aqueous solubility and to maximize the fluorescence of the ultimate 1-arylfurochromone fluorophore.An efficient synthetic pathway to the furyl chromones via an intramolecular Dieckman cyclization also is described.
