66508-99-4

Upstream product

• 108-94-1 cyclohexanone 
• 90-02-8 salicylaldehyde 

Relevant academic research and scientific papers

Network reaction of 2,6-bis(2-hydroxybenzilidene)cyclohexanone by external stimuli

The pH-dependent photochromic behaviour of a curcumin analogue, 2,6-bis(2-hydroxybenzilidene)cyclohexanone (HBC) has been investigated. The identification of stable and unstable species from network reaction was done by combination of NMR, UV-vis and fluo

Anti-inflammatory activity of ortho-trifluoromethoxy-substituted 4-piperidione-containing mono-carbonyl curcumin derivatives in vitro and in vivo

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.

Exploring the unexpected formation of spirobibenzopyrans and benzopyrylium salts and effect of Lewis acids on the Claisen-Schmidt reaction

Unexpected spiro cyclic products were obtained from the popular alkali catalyzed Claisen-Schmidt reaction of ketones with salicylaldehyde apart from the bis-chalcones. However, in the acid catalyzed reaction, we observe their transformation to a benzopyry

Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes

Objectives A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro. Methods The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique. Key findings Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration. Conclusions The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.

Sulfamic acid: An efficient, cost-effective and green catalyst for crossed-aldol condensation of ketones with aromatic aldehydes under solvent-free

Aromatic aldehydes undergo crossed-aldol condensation with ketones in the presence of catalytic amount of sulfamic acid (SA) to afford the corresponding α, β-unsaturated aldol products under solvent-free conditions in good to high yields at 45-80 °C.

Antioxidation and tyrosinase inhibition of polyphenolic curcumin analogs

A series of polyphenolic curcumin analogs were synthesized and their inhibitory effects on mushroom tyrosinase and the inhibition of 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical formation were evaluated. The results indictated that the analogs posses