929110-66-7

Upstream product

• 160096-61-7 1E,6E-1,7-bis(4-methoxyphenyl)hepta-1,6-diene-3,5-dione 
• 123-11-5 4-methoxy-benzaldehyde 
• 123-54-6 acetylacetone 

Downstream Products

• 1227098-22-7 (1E,6E)-1,7-bis(4-methoxyphenyl)-4-(2,3,4-trimethoxybenzylidene)hepta-1,6-diene-3,5-dione 
• 1227098-16-9 (1E,6E)-4-(4-hydroxy-3-methoxybenzylidene)-1,7-bis(4-methoxyphenyl)hepta-1,6-diene-3,5-dione 
• 1227098-21-6 (1E,6E)-4-(3,4-dimethoxybenzylidene)-1,7-bis(4-methoxyphenyl)hepta-1,6-diene-3,5-dione 
• 1257441-70-5 (1E,6E)-4-(hydroxymethylene)-1,7-bis(4-methoxyphenyl)hepta-1,6-diene-3,5-dione 

Relevant academic research and scientific papers

Method for artificially synthesizing curcumin and derivative thereof

The invention discloses a method for artificially synthesizing curcumin and a derivative thereof. The method comprises the steps of adopting calcium acetylacetonate as a acetylacetone supply source, carrying out claisen-schmidt ester condensation reaction on the calcium acetylacetonate and a corresponding benzaldehyde derivative, and dehydrating under the catalysis of a dehydrating agent which is tributyl borate to obtain a product intermediate (I) which is curcumin calcium salt; then hydrolyzing the intermediate (I) through a one-pot method to obtain a crude product, and purifying the crude product so as to obtain the final product curcumin and the derivative thereof. Compared with a acetylacetone boric acid complex method, according to the method provided by the invention, the calcium acetylacetonate is used, so that active sites of acetylacetonate during a reaction process are more accurate and activated, the generation of by-products is reduced, and the yield of the curcumin and the derivative thereof is improved.

Versatility of the Curcumin Scaffold: Discovery of Potent and Balanced Dual BACE-1 and GSK-3β Inhibitors

The multitarget approach has gained increasing acceptance as a useful tool to address complex and multifactorial maladies such as Alzheime?s disease (AD). The concurrent inhibition of the validated AD targets β-secretase (BACE-1) and glycogen synthase kin

The in vitro antitumor activity of arene-ruthenium(II) curcuminoid complexes improves when decreasing curcumin polarity

The antitumor activity of ruthenium(II) arene (p-cymene, benzene, hexamethylbenzene) derivatives containing modified curcumin ligands (HCurcI?=?(1E,4Z,6E)-5-hydroxy-1,7-bis(3,4-dimethoxyphenyl)hepta-1,4,6-trien-3-one and HCurcII?=?(1E,4Z,6E)-5-hydroxy-1,7-bis(4-methoxyphenyl)hepta-1,4,6-trien-3-one) is described. These have been characterized by IR, ESI-MS and NMR spectroscopy. The X-ray crystal structure of HCurcI has been determined and compared with its related Ru complex. Four complexes have been evaluated against five tumor cell lines, whose best activities [IC50 (μM)] are: breast MCF7, 9.7; ovarian A2780, 9.4; glioblastoma U-87, 9.4; lung carcinoma A549, 13.7 and colon-rectal HCT116, 15.5; they are associated with apoptotic features. These activities are improved when compared to the already known corresponding curcumin complex, (p-cymene)Ru(curcuminato)Cl, about twice for the breast and ovarian cancer, 4.7 times stronger in the lung cancer and about 6.6 times stronger in the glioblastoma cell lines. In fact, the less active (p-cymene)Ru(curcuminato)Cl complex only shows similar activity to two novel complexes in the colon cancer cell line. Comparing antitumor activity between these novel complexes and their related curcuminoids, improvement of antiproliferative activity is seen for a complex containing CurcII in A2780, A549 and U87 cell lines, whose IC50 are halved. Therefore, after replacing OH curcumin groups with OCH3, the obtained species HCurcI and its Ru complexes have increased antitumor activity compared to curcumin and its related complex. In contrast, HCurcII is less cytotoxic than curcumin but its related complex [(p-cymene)Ru(CurcII)Cl] is twice as active as HCurcII in 3 cell lines. Results from these novel arene-Ru curcuminoid species suggest that their increased cytotoxicity on tumor cells correlate with increase of curcuminoid lipophilicity.

Mechanochemical synthesis of 2,2-difluoro-4, 6-bis(β-styryl)-1,3,2-dioxaborines and their use in cyanide ion sensing

The conversion of arylaldehydes to 1,7-diaryl-5-hydroxyhepta-1,4,6-trien-3-ones (curcuminoids) and the mechanochemical cyclization of these products to 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines using BF3-Et2O are described. Investigation of the cyanide ion sensing ability of the 2,2-difluoro-4,6-bis(β-styryl)-1,3,2-dioxaborines, in relation to the substituent groups on the aryl ring, showed that a hydroxy susbstituent is required, preferably para to the intervening carbon bridge.

Iodine impregnated nano neutral alumina as an efficient catalyst for one pot green synthesis of curcumin analogues by microwave irradiation

Sixteen substituted curcumin analogs are synthesized in one pot by iodine impregnated nano neutral alumina catalyst under microwave irradiation. This catalyst shows higher reactivity by which it offered the reaction with higher yields and less reaction time. The prepared catalyst was characterized by FE-SEM, EDX and BET isotherm surface area. Also, the synthesized products were characterized by FT-IR, 1H NMR, 13C NMR, mass and elemental analysis.

Synthesis and photophysical properties of difluoroboron complexes of curcuminoid derivatives bearing different terminal aromatic units and a meso-aryl ring

The synthesis of nine curcuminoids and their difluoroboron complexes is described, with seven of them containing a meso-phenyl ring. Dynamic 19F NMR confirmed the fact that rotation of that meso-aryl fragment is restricted in the latter systems at room temperature and become allowed at higher temperature (>45 C). The molecular structure of a meso-substituted derivative in the solid state showed that the phenyl ring lies in a highly twisted plane with respect to the mean curcuminoid plane. The photophysical properties of the nine compounds were investigated in solvents of different polarity. Meso-substitution with a phenyl ring has little influence on fluorescence emission properties in solution, radiative and nonradiative kinetic constants being similar for meso- and nonsubstituted compounds, which is in contrast to the case of BODIPY derivatives. However, introduction of an electron donor p-methoxy group at the meso-phenyl ring leads to small perturbation of the curcuminoid π-system fluorescence emission. We also report the influence of the meso-phenyl group on the emission properties of the aggregated solids.

Synthesis and identification of new 4-arylidene curcumin analogues as potential anticancer agents targeting nuclear factor-κB signaling pathway

A series of curcumin analogues including new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized. Cell growth inhibition assays revealed that most 4-arylidene curcumin analogues can effectively decrease the growth of a panel of lung cancer cells at submicromolar and low micromolar concentrations. High content analysis technology coupled with biochemical studies showed that this new class of 4-arylidene curcumin analogues exhibits significantly improved NF-κB inhibition activity over the parent compound curcumin, at least in part by inhibiting IκB phosphorylation and degradation via IKK blockage; selected 4-arylidene curcumin analogues also reduced the tumorigenic potential of cancer cells in a clonogenic assay.

COMPOUNDS WITH (SUBSTITUTED PHENYL)-PROPENAL MOIETY, THEIR DERIVATIVES, BIOLOGICAL ACTIVITY, AND USES THEREOF

The present invention includes compounds, pharmaceuticals and cosmetics having at least one (substituted phenyl)-propenal moiety. The compounds and compositions of the present invention are useful in the treatment or prevention of many medical conditions such as androgen associated conditions. The present invention also includes methods of treating a medical condition including an androgen associated condition, using at least one of the disclosed compounds.

Synthesis and evaluation of curcumin analogues as potential thioredoxin reductase inhibitors

Series of curcumin derivatives were synthesized; the inhibitory activities on thioredoxin reductase (TrxR) of all analogues were evaluated by DTNB assay in vitro. It is found that most of the analogues can inhibit TrxR in the low micromolar range; Structure-activity relationship analysis reveals that analogues with furan moiety have excellent inhibitory effect on TrxR in an irreversible manner, indicating that the furan moiety may serve as a possible pharmacophore during the interaction of curcumin analogues with TrxR. The effect of selected curcuminoids on growth of different TrxR overexpressed cancer cell lines was also investigated and discussed.

A comparative study on the antioxidant properties of tetrahydrocurcuminoids and curcuminoids

Several curcuminoids and tetrahydrocurcuminoids (THCs), bearing various hydroxyl and/or methoxy groups on their benzene rings, have been synthesized to study their antioxidant and hydrogen donating capacities using the DPPH method at 25 °C in methanol. The results show that the tetrahydrocurcuminoids are in general much more efficient than their curcuminoid analogs if they include a phenol group in meta- or para-position of the linking chain and a neighboring phenol or methoxy group. This efficiency gain of THCs by comparison to curcuminoids was attributed to the presence of benzylic hydrogens involved in the oxidation process of these compounds and not to the beta-diketone moiety in the chain.