1019110-87-2

Upstream product

• 458-37-7 curcumin 
• 59-88-1 phenylhydrazine hydrochloride 
• 814919-70-5 (1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one 
• 100-63-0 phenylhydrazine 
• 458-37-7 curcumin 
• 123-54-6 acetylacetone 
• 121-33-5 vanillin 

Relevant academic research and scientific papers

Synthesis and antiproliferative studies of curcumin pyrazole derivatives

A series of curcumin pyrazole derivatives (3a–e) were synthesized. The chemical structures were determined by 1H and 13C NMR spectroscopic techniques and their purity was confirmed by LC–MS and melting point determination. The compou

Antioxidant activity and electrochemical elucidation of the enigmatic redox behavior of curcumin and its structurally modified analogues

Here, we report studies on the antioxidant activity and redox behavior of curcumin and its structurally modified synthetic analogues. We have synthesized a number of analogues of curcumin which abrogate its keto-enol tautomerism or substitute the methylene group at the centre of its heptadione moiety implicated in the hydride transfer and studied their redox property. From cyclic voltammetric studies, it is demonstrated that H- atom transfer from CH2 group at the center of the heptadione link also plays an important role in the antioxidant properties of curcumin along with that of its phenolic -OH group. In addition, we also show that the conversion of 1, 3- dicarbonyl moiety of curcumin to an isosteric heterocycle as in pyrazole curcumin, which decreases its rotational freedom, leads to an improvement of its redox properties as well as its antioxidant activity.

Mechanochemical Synthesis and Antioxidant Activity of Curcumin-Templated Azoles

A solvent-free, mechanochemical method for the synthesis of curcumin (1) derived 3,5-bis(styryl)pyrazoles and 3,5-bis(styryl)isoxazole (2a-g) at room temperature, with very short reaction time, is reported. Such earlier structural modifications of curcumin, at its β-diketone unit by transforming it into an isosteric pyrazole or isoxazole unit, required prolonged heating. The evaluation of the antioxidant activity of these compounds, based on DPPH, FRAP, and β-carotene bleaching assays, showed that several of these azoles are better antioxidants than curcumin, with the isoxazole derivative 2g being overall the best. Typically, the inhibition of 2,2-diphenyl-1-picrylhydrazyl (10-2 mmol), expressed as EC50 values, by curcumin (1), 3,5-bis(4-hydroxy-3-methoxystyryl)pyrazole (2a), and 3,5-bis(4-hydroxy-3-methoxystyryl)isoxazole (2g) are 40 ± 0.06, 14 ± 0.18, and 8 ± 0.11 μmol, respectively. Moreover, the reported method is useful in accessing 3,5-bis(4-hydroxy-3-methoxystyryl)-1-phenylpyrazole (2b), which is important in studies related to neuroprotection and Alzheimer's disease, and 2a and 2g, which are inhibitors of protein kinases involved in neuronal excitotoxicity.

The inhibitory role of curcumin derivatives on AMPA receptor subunits and their effect on the gating biophysical properties

Curcumin is a natural polyphenol that has a broad spectrum of therapeutic characters, including neuroprotective actions against various neurological diseases. However, the molecular mechanism behind its neuroprotective properties remains obscure. The curr

Synthesis of curcuminoids and evaluation of their cytotoxic and antioxidant properties

Curcumin (1) and ten derivatives (2-11) were synthesized and evaluated as cytotoxic and antioxidant agents. The results of primary screening by Sulforhodamine B assay against five human cancer cell lines (U-251 MG, glioblastoma; PC-3, human prostatic; HCT-15, human colorectal; K562, human chronic myelogenous leukemia; and SKLU-1, non-small cell lung cancer) allowed us to calculate the half maximal inhibitory concentration (IC50) values for the more active compounds against HCT-15 and K562 cell lines. Compounds 2 and 10 were the most active against both cell lines and were more active than curcumin itself. Thiobarbituric acid reactive substances (TBARS) assay showed that 7 has potent activity; even stronger than curcumin, α-tocopherol, and quercetin.

Screening of curcumin-derived isoxazole, pyrazoles, and pyrimidines for their anti-inflammatory, antinociceptive, and cyclooxygenase-2 inhibition

Curcumin has shown pharmacological properties against different phenotypes of various disease models. Different synthetic routes have been employed to develop its numerous derivatives for diverse and improved therapeutic roles. In this study, we have synt

Studies on the antioxidant activities of mechanochemically synthesized 1-aryl-3,5-Bis(Styryl) pyrazoles as curcuminoids derived CNB 001 analogs

1-Aryl-3,5-bis(styryl)pyrazoles, as analogs of CNB 001, a well investigated, curcumin derived neuroprotector, have been accessed through rapid, energy efficient mechanochemical synthesis starting from curcuminoids. A study of their anti-oxidant activity i

Antioxidant and hypoglycemic effects of curcumin pyrazole derivatives

Objective: To investigate the antioxidant properties of curcumin pyrazole derivatives using different in-vitro models and hypoglycemic potential by gluconeogenesis studies. Methods: Antioxidant ability of curcumin pyrazole derivatives was evaluated by using DPPH, nitric oxide, superoxide anion scavenging and lipid peroxidation assays comparing with standard, ascorbic acid (AA). The hypoglycemic effects of the compounds (3a-3e) were assessed by gluconeogenesis inhibition assay using rat liver slices comparing with standard, Insulin. Results: Compounds demonstrated strong scavenging activities against 2, 2-diphenyl, 2-picryl hydrazyl (DPPH), nitric oxide, superoxide anion radicals and also effectively inhibited lipid peroxidation. Compounds 3a, 3b and 3e exhibited significant activity in quenching DPPH, superoxide anion radical, nitric oxide and showed anti-lipid peroxidation. Other compounds 3c and 3d showed moderate activities. The gluconeogenesis inhibitory effects were more pronounced with compounds 3a and 3b compared to compounds 3c, 3d and 3e. Conclusion: Curcumin pyrazole derivatives showed considerable antioxidant activity against free radicals and lipid peroxidation. They exhibited significant IC50values and thus can promote prominent protection against oxidative damage. The compounds 3a and 3b could be promising hypoglycemic agents as they are capable of lowering blood glucose by inhibiting gluconeogenesis and can be selected for further in-vitro and in vivo anti-diabetic investigations.

Curcumin is an inhibitor of calcium/calmodulin dependent protein kinase II

Calcium/calmodulin dependent protein kinase II (CaMKII) is involved in the mechanisms underlying higher order brain functions such as learning and memory. CaMKII participates in pathological glutamate signaling also, since it is activated by calcium influx through the N-methyl-d-aspartate type glutamate receptor (NMDAR). In our attempt to identify phytomodulators of CaMKII, we observed that curcumin, a constituent of turmeric and its analogs inhibit the Ca2+-dependent and independent kinase activities of CaMKII. We further report that a heterocyclic analog of curcumin I, (3,5-bis[β-(4- hydroxy-3-methoxyphenyl)ethenyl]pyrazole), named as pyrazole-curcumin, is a more potent inhibitor of CaMKII than curcumin. Microwave assisted, rapid synthesis of curcumin I and its heterocyclic analogues is also reported.

Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity

Curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3), the curcuminoid constituents of the medicinal plant Curcuma longa L., have been structurally modified to 55 analogs and antimycobacterial activity against Mycobacterium tuberculosis has been evaluated. Among the highly active curcuminoids, the isoxazole analogs are the most active group, with mono-O-methylcurcumin isoxazole (53) being the most active compound (MIC 0.09 μg/mL). It was 1131-fold more active than curcumin (1), the parent compound, and was approximately 18 and 2-fold more active than the standard drugs kanamycin and isoniazid, respectively. Compound 53 also exhibited high activity against the multidrug-resistant M. tuberculosis clinical isolates, with the MICs of 0.195-3.125 μg/mL. The structural requirements for a curcuminoid analog to exhibit antimycobacterial activity are the presence of an isoxazole ring and two unsaturated bonds on the heptyl chain. The presence of a suitable para-alkoxyl group on the aromatic ring which is attached in close proximity to the nitrogen function of the isoxazole ring and a free para-hydroxyl group on another aromatic ring enhances the biological activity.