90934-85-3

Upstream product

• 100-52-7 benzaldehyde 
• 123-54-6 acetylacetone 
• 26567-75-9 acetylacetone enol 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 881915-91-9 4,4-dibenzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione 
• 38572-30-4 1,7-bisphenylheptane-3,5-dione 
• 98886-21-6 4-Benzyl-1,7-diphenyl-1,6-heptadiene-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.

Design, synthesis, and evaluation of curcumin derivatives as Nrf2 activators and cytoprotectors against oxidative death

Activation of nuclear factor erythroid-2-related factor 2 (Nrf2) has been proven to be an effective means to prevent the development of cancer, and natural curcumin stands out as a potent Nrf2 activator and cancer chemopreventive agent. In this study, we synthesized a series of curcumin analogs by introducing the geminal dimethyl substituents on the active methylene group to find more potent Nrf2 activators and cytoprotectors against oxidative death. The geminally dimethylated and catechol-type curcumin analog (compound 3) was identified as a promising lead molecule in terms of its increased stability and cytoprotective activity against the tert-butyl hydroperoxide (t-BHP)-induced death of HepG2 cells. Mechanism studies indicate that its cytoprotective effects are mediated by activating the Nrf2 signaling pathway in the Michael acceptor- and catechol-dependent manners. Additionally, we verified by using copper and iron ion chelators that the two metal ion-mediated oxidations of compound 3 to its corresponding electrophilic o-quinone, contribute significantly to its Nrf2-dependent cytoprotection. This work provides an example of successfully designing natural curcumin-directed Nrf2 activators by a stability-increasing and proelectrophilic strategy.

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 characterization of new curcumin derivatives as potential chemotherapeutic and antioxidant agents

Preclinical Research The purpose of this work was to synthesize a series of symmetrical analogs (CA2-CA7) of curcumin and determine their efficacy as antioxidant and anticancer agents in vitro. The six analogs were successfully synthesized and characterized, one of which, CA6, had not been previously reported in the literature. With the exception of CA2, the analogs had lower predicted aqueous solubilities and higher partition coefficients than curcumin. Two analogs, CA2 and CA3, had lower potencies as anticancer agents compared with curcumin, while CA6 had a slightly higher IC50 value. Two different trends in the antioxidant capabilities of curcumin and its analogs were determined when assessed in vitro or in cell culture. The in vitro DPPH assay clearly showed curcumin as the strongest antioxidant as compared with the analogs when tested at the same concentration or at their IC50 value. The cell culture-based reactive oxygen species/reactive nitrogen species assay indicated that CA3 and CA6 were equal to curcumin in their free radical scavenging ability at the same concentration, but when curcumin and its analogs were tested at their respective IC50 values, CA4 and CA5 showed excellent antioxidant capacities. These results indicate that in cell culture, the ability of these analogs to produce antioxidant effects may be tied to their downstream effects.

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.

Activation of NFκB is inhibited by curcumin and related enones

The transcription factor NFkappaB (NFκB) is up-regulated in many cancer cells where it contributes to development of the pro-survival, anti-apoptotic state. The natural product curcumin is a known inhibitor of activation of NFκB. Enone analogues of curcumin were compared with curcumin for their abilities to inhibit the TNFα-induced activation of NFκB, using the Panomics' NFκB Reporter Stable Cell Line. The enones tested included curcumin analogues that retained the 7-carbon spacer between the aromatic rings, analogues with a 5-carbon spacer, and analogues with a 3-carbon spacer. Inhibitors of NFκB activation were identified in all three series, a number of which were more active than curcumin. Enone analogues in the series with the 5-carbon spacer were especially active, including members that contained heterocyclic rings. 1,5-Bis(3-pyridyl)-1,4-pentadien-3-one was the most active analogue, IC50 = 3.4 ± 0.2 μM. The most active analogues retain the enone functionality, although some analogues devoid of the enone functionality exhibited activity. The activity of the analogues as inhibitors of the activation of NFκB did not correlate with their anti-oxidant activity. The data suggest that the abilities of curcumin and analogues to prevent the stress-induced activation of NFκB result from the inhibition of specific targets rather than from activity as anti-oxidants.

TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin

The activator protein-1 (AP-1) family of transcription factors, including the most common member c-Jun-c-Fos, participates in regulation of expression of numerous genes involved in proliferation, apoptosis, and tumorigenesis in response to a wide array of stimuli including pro-inflammatory cytokines, growth factors, stress, and tumor promoters. A number of plant polyphenols including curcumin, a yellow compound in the spice turmeric, have been shown to inhibit the activation of AP-1. Curcumin is a polyphenolic dienone that is potentially reactive as a Michael acceptor and also is a strong anti-oxidant. Multiple activities reported for curcumin, including inhibition of the stress-induced activation of AP-1, have been suggested to involve the anti-oxidant properties of curcumin. In the present study, a library of analogs of curcumin was screened for activity against the TPA-induced activation of AP-1 using the Panomics AP-1 Reporter 293 stable cell line which is designed for screening potential inhibitors. Numerous analogs were identified that were more active than curcumin, including analogs that were not anti-oxidants and analogs that were not Michael acceptors. Clearly, anti-oxidant activity or reactivity as a Michael acceptor is not an essential feature of active compounds. In addition, a number of analogs were identified that enhanced the TPA-induced activation of AP-1. The results from screening were confirmed using BV-2 microglial cells where curcumin and analogs were shown to inhibit LPS-induced COX-2 expression; analogs identified as more potent than curcumin in the screening assay were also more potent than curcumin in preventing COX-2 expression.

Pharmaceutical compositions useful in prevention and treatment of beta-Amyloid protein-induced disease

The invention provides methods for treating beta-Amyloid protein-induced disease, pharmaceutical compositions and compounds useful for the same, and the use of these compounds for the manufacture of a medicament for treating the same. More particularly, the invention relates to the use of natural product compounds isolated from turmeric, gingko biloba, and ginger, and synthetic chemical analogues thereof, for the treatment of a beta-Amyloid protein-induced disease.

Total synthesis and anti-leishmanial activity of some curcumin analogues

Curcumin (1) an important yellow dye isolated from Curcuma longa rhizomes, exhibits a variety of pharmacological effects such as anti-inflammatory, antioxidant and antiviral activity. Ten curcuminoids (2-11) were synthesized by the condensation of 2,4-pentanedione with differently substituted benzaldehydes, using the boron complex approach, which avoided Knoevenagel condensation at C-3 of the diketone. The curcuminoids were assayed in vitro against Leishmania amazonensis promastigotes using pentamidine isethionate (CAS 140-64-7) as the reference drug. Compound (5) 1,7-bis-(2-hydroxy-4-methoxyphenyl)-1,6-heptadiene-3,5-dione) was the most effective.