342807-89-0

Usage

Physical state at room temperature

Yellow crystalline solid

Natural occurrence

Found in plants such as Angelica keiskei and composite plants, specifically in the flowers

Uses

Widely used in the synthesis of various pharmaceuticals and agrochemicals

Biological activities

Exhibits antimicrobial, anticancer, and anti-inflammatory properties

Additional properties

Possesses antioxidant and radical-scavenging effects

Potential applications

Development of new therapeutic agents

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 67-64-1 acetone 

Downstream Products

• 1427054-08-7 1,5-bis(3-hydroxyphenyl)pentan-3-one 

Relevant academic research and scientific papers

A monocarbonyl analogue of curcumin, 1,5-bis(3-hydroxyphenyl)-1,4- pentadiene-3-one (Ca 37), exhibits potent growth suppressive activity and enhances the inhibitory effect of curcumin on human prostate cancer cells

Prostate carcinoma is one of the leading causes of cancer-related morbidity and mortality in males in western countries. Curcumin exhibits growth-suppressive activity against several cancers, including prostate cancer, but it has poor bioavailability. The purpose of this study was to evaluate the anticancer potency and mechanism of a curcumin analogue, 1,5-bis(3- hydroxyphenyl)-1,4-pentadiene-3-one (Ca 37), in human prostate cancer. Studies were performed in established human prostate cancer cell lines (PC-3 and DU145) as well as in a murine xenograft tumor (PC-3) model. Ca 37 presented a preferential suppression capacity against growth and migration toward prostate cancer cells compared with curcumin. Ca 37 impaired the bioenergetics system, promoted cell cycle arrest and apoptosis activation in PC-3 cells. In addition, 0.5 μmol (6.65 mg/kg body weight) of Ca 37 significantly inhibited the growth of the prostate xenografted tumors, whereas 6 μmol (110 mg/kg body weight) of curcumin had little effect. Furthermore, a combination of Ca 37 and curcumin resulted in enhanced antitumor activity in prostate cancer cells. N-Acetylcysteine abrogated both reactive oxygen species (ROS) production and viability loss induced by Ca 37 but partially prevented growth inhibition in PC-3 cells treated with curcumin alone, or a combination with Ca 37. The data indicate that induction of ROS plays a vital role in the growth inhibitory effect of Ca 37 in PC-3 cells. This study suggests that Ca 37, alone or in combination with curcumin, may be a promising anticancer agent for prostate cancer therapy.

A ligand synthesis of butadiene adhesive

The invention relates to a synthesis method of ligand butadiene adhesive, to 3 - hydroxybenzaldehyde with acetone as the starting material, condensation to obtain the 1, 5 - double-(3 - hydroxy-phenyl) - 1, 4 - isoprene ketone, the 1, 5 - double-(3 - hydr

1,5-DIPHENYL-PENTA-1,4-DIEN-3-ONE COMPOUNDS

This invention relates to compounds of Formula (I), (II), or (III) as shown in the specification, which contain a 1,5-diphenylpenta-1,4-dien-3-one backbone. These compounds can be used to treat cancer, inflammatory disease, or autoimmune disease.

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.

Benzylic ligand hydroxylation starting from a dicopper μ- I·2:I·2 peroxo intermediate: Dramatic acceleration of the reaction by hydrogen-atom donors

Radicals in directed pathways: The μ-I·2: I·2 peroxo CuII2 intermediate 1 shows a much faster benzylic ligand hydroxylation than systems without phenol. This novel reactivity can be further accelerated by addition of external H-atom donors such as TEMPO-H. The results imply initial H-atom transfer leading to the formation of phenoxyl radicals. A highly reactive copper oxyl intermediate is then formed, which inserts oxygen into the benzylic C-H bond. Copyright

Synthesis and biological evaluation of curcumin-like diarylpentanoid analogues for anti-inflammatory, antioxidant and anti-tyrosinase activities

A series of 46 curcumin related diarylpentanoid analogues were synthesized and evaluated for their anti-inflammatory, antioxidant and anti-tyrosinase activities. Among these compounds 2, 13 and 33 exhibited potent NO inhibitory effect on IFN-γ/LPS-activated RAW 264.7 cells as compared to l-NAME and curcumin. However, these series of diarylpentanoid analogues were not significantly inhibiting NO scavenging, total radical scavenging and tyrosinase enzyme activities. The results revealed that the biological activity of these diarylpentanoid analogues is most likely due to their action mainly upon inflammatory mediator, inducible nitric oxide synthase (iNOS). The present results showed that compounds 2, 13 and 33 might serve as a useful starting point for the design of improved anti-inflammatory agents.