41973-42-6Relevant academic research and scientific papers
Anti-inflammatory activity of ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives in vitro and in vivo
Wang, Ziqing,Mu, Wenwen,Li, Pengxiao,Liu, Guoyun,Yang, Jie
, (2021/02/21)
Curcumin was reported as an anti-inflammatory agent. However, curcumin's poor bioavailability limited its clinical utility. Here, thirty ortho-substituted mono-carbonyl curcumin derivatives, containing acetone, cyclopentanone, cyclohexanone or 4-piperidione (N—H, N-methyl or N-acrylyl) moieties replacing β-diketone moiety of curcumin, were investigated for anti-inflammatory activity. Two active ortho-trifluoromethoxy-substituted 4-piperidione-containing derivatives 22 and 24 owned good cell uptake ability, and displayed excellent anti-inflammatory activity in both lipopolysaccharide-induced Raw264.7 macrophages and a dextran sulfate sodium (DSS)-induced mouse model of colitis. They inhibited the production of nitric oxide, reactive oxygen species, malonic dialdehyde and cyclooxygenase-2; and the expression of pro-inflammatory cytokines interleukin-1β, tumor necrosis factor-α and myeloperoxidase; the phosphorylation of mitogen-activated protein kinases; and the nucleus translocation of p65. What's more, 22 or 24 oral administered reduced the severity of clinical symptoms of ulcerative colitis (body weight and disease activity index), and reduced obviously DSS-induced colonic pathological damage (the colon length and histopathology analysis). These results suggested that ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives 22 and 24 were potential anti-inflammatory agents; and offered the important information for design and discovery of more potent anti-inflammatory drug candidates.
Tandem hydrogenation and condensation of fluorinated α,β-unsaturated ketones with primary amines, catalyzed by nickel
Castellanos-Blanco, Nahury,Flores-Alamo, Marcos,García, Juventino J.
supporting information, p. 15653 - 15663 (2015/09/07)
A simple homogeneous catalytic system based on nickel phosphine complexes has been developed for the transfer hydrogenation and condensation of α,β-unsaturated ketones to yield saturated ones and saturated imines using primary amines as hydrogen donors. Thus, a wide range of fluorinated 1,5-diaryl-1,4-pentadiene-3-ones were allowed to react with substituted benzylamines in the presence of [(dippe)Ni(μ-H)]2 (dippe = 1,2-bis-(diisopropylphosphino)-ethane) using ethanol as a solvent at 180 °C to give the corresponding saturated carbonyl compounds; here hydrogenation of the CC bond was preferred over the CO bond. Under the same reaction conditions but using an excess of benzylamine, a tandem process is then favoured, starting also with the reduction of the CC bond followed by a nucleophilic addition of the primary amine to yield valuable saturated imines with good to excellent yields (62%-91%).
Mild and ecofriendly tandem synthesis, and spectral and antimicrobial studies of n1-acetyl-5-aryl-3-(substituted styryl)pyrazolines
Pathak, Vijai N.,Joshi, Rahul,Sharma, Jaimala,Gupta, Neetu,Rao, Vijay Mohan
experimental part, p. 1854 - 1865 (2010/01/17)
N1-acetyl-5-aryl-3-(substituted styryl)pyrazolines were synthesized by the cyclocondensation of 1,5-substituted diphenyl-1,4-pentadien-3-ones with hydrazine hydrate and a cyclizing agent such as acetic acid in ethanol. The title compounds were synthesized using conventional and solvent-free approaches, which involves mechano-chemical mixing, microwave-irradiation, and ultrasound-irradiation methods in the presence of a solid support. The synthesized compounds have been characterized by elemental analyses and spectral data (IR, PMR, and FAB-mass). All the synthesized compounds have been evaluated for their antibacterial and antifungal activities. Some compounds have shown promising biological activity.
Study of substituent effects in substituted dibenzal acetones
Ananthakrishna Nadar,Renuga
, p. 1219 - 1222 (2008/09/21)
The present work involves a detailed study of the ultra-violet absorption spectra of various substituted dibenzylidene ketones derived from acetone, ethyl methyl ketone, diethyl ketone, cyclopentanone and cyclohexanone by condensing with several meta- and para-substituted benzaldehydes in n-hexane and in ethanol to ascertain the transition dominant in these solvents. These ketones exist as equilibrium mixtures of s-cis, cis and s-cis, trans conformations. The ultraviolet absorption spectra of the ketones exhibit two bands due to π* ← π transition around 250 and 320 nm. The 320 nm band is prominent in all the cases. There is no indication of π* ← n transition in any of the spectra. The 320 nm band is structureless in all the cases except those shown by the dibenzylidene ketones derived from cyclopentanone in hexane. Therefore it can be inferred that the dibenzylide ketones derived from all the ketones except those derived from cyclopentanone are non-planar.
Debromination of Chalkone Dibromides and Dibenzalacetone Dibromides with Sodium Hydrogen Selenide
Raja, T. K.
, p. 812 - 813 (2007/10/02)
Chalkone dibromides (Ia-c) undergo debromination when treated with sodium hydrogen selenide in boiling ethanol to give chalkones (IIa-c).Likewise dibenzalacetone dibromides (IIIa-c) suffer debromination to give dibenzalacetones (IVa-c) which further interact with sodium hydrogen selenide to give 2,4-diaryltetrahydroselenopyran-4-ones (Va-c).
