18423-13-7

Upstream product

• 122850-52-6 4-(1,1-dimethyl-2-propynyloxy)-3-methoxy benzaldehyde 
• 121-33-5 vanillin 
• 870-63-3 prenyl bromide 

Downstream Products

• 1039071-49-2 (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxy-3-methoxy-5-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one 
• 1442415-88-4 C₁₇H₂₄O₅ 
• 1442415-87-3 5′,5″-diisoamyltetrahydrocurcumin 

Relevant academic research and scientific papers

Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity

Curcumin (CCM) is a well-known active component, which has been studied extensively in food and medicine field since it showed various activities. However, some serious issues limit its application, for example, the extremely low solubility, stability and

Novel curcumin analogue, preparation method and application thereof

The invention relates to a novel curcumin analogue. The analogue is obtained by modifying curcumin with a substituent common in natural products. Specifically, the general structural formula of the analogue is shown as the specification, wherein R1 and R2

Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents

An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C (1), stipulin (2), crotaorixin (3), medicagenin (4), licoagrochalcone A (5) and abyssinone D (6) along with the pyranochalcones paratocarpin C (7), anthyllisone (8) and 3-O-methylabyssinone A (9). The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides (LPSs)-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 (IC50 = 10.41 μmol/L), 6 (IC50 = 9.65 μmol/L) and 8 (IC50 = 15.34 μmol/L) show remarkable activity with no cytotoxicity. Compound 9 (IC50 = 4.5 μmol/L) exhibits maximum (83.6%) nitric oxide (NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A (acetophenone moiety), i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B (aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.

Dissecting the pharmacophore of curcumin. Which structural element is critical for which action?

The dietary phenolic curcumin (1a) is the archetypal network pharmacological agent, but is characterized by an ill-defined pharmacophore. Nevertheless, structure-activity studies of 1a have mainly focused on a single biological end-point and on a single structural element, the aliphatic bis-enoyl moiety. The comparative investigation of more than one end-point of curcumin and the modification of its aromatic region have been largely overlooked. To address these issues, we have investigated the effect of aromatic C-prenylation in the three archetypal structural types of curcuminoids, namely, curcumin itself (1a), its truncated analogue 2a (C5-curcumin), and (as the reduced isoamyl version) the tetrahydro derivative 3a, comparatively evaluating reactivity with thiols and activity in biochemical (inhibition of NF-κB, HIV-1-Tat transactivation, Nrf2 activation) and phenotypic (anti-HIV action) assays sensitive, to a various extent, to thia-Michael addition. Prenylation, a validated maneuver for bioactivity modulation in plant phenolics, had no effect on Michael reactivity, but was detrimental for all biological end-points investigated, dissecting thiol trapping from activity, while hydrogenation attenuated, but did not completely abrogate, the activity of 1a. The C 5-curcuminoid 2a outperformed the natural product in all end-points investigated and was identified as a novel high-potency anti-HIV lead in a cellular model of HIV infection. Taken together, these observations show that Michael reactivity is a critical element of the curcumin pharmacophore, but also reveal a surprising sensitivity of bioactivity to C-prenylation of the vanillyl moiety.