22214-39-7

Usage

Uses

Used in Pharmaceutical Applications:
(E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one is used as a therapeutic agent for its antioxidant and anti-inflammatory properties, which contribute to its potential in treating various diseases such as cancer, neurodegenerative disorders, and cardiovascular conditions. Its natural origin and biological activities make it an attractive compound for the development of novel pharmaceuticals.
Used in Cancer Treatment:
In the field of oncology, (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one is used as a potential anticancer agent. Its antioxidant properties may help protect cells from damage that can lead to cancer, while its anti-inflammatory effects could reduce inflammation associated with tumor growth. Further research is needed to explore its full potential in cancer treatment.
Used in Neurodegenerative Disorder Treatment:
(E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one is also being investigated for its use in treating neurodegenerative disorders. Its antioxidant properties could help combat oxidative stress, a common factor in many neurodegenerative conditions, potentially slowing disease progression and improving patient outcomes.
Used in Cardiovascular Condition Treatment:
In the cardiovascular field, (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one is used as a potential treatment for various heart-related conditions. Its antioxidant and anti-inflammatory properties may help reduce the risk of cardiovascular diseases by protecting the heart and blood vessels from damage and inflammation.
Used in Research and Development:
(E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one is used as a subject of study in research and development for its unique chemical structure and biological activities. Scientists and pharmaceutical companies are interested in understanding its full potential and how it can be harnessed for the development of new drugs and therapies across various medical fields.

Upstream product

• 621-59-0 isovanillin 
• 67-64-1 acetone 

Downstream Products

• 213264-84-7 4-(4-methoxy-3-methoxymethoxyphenyl)-2-buten-3-one 
• 1391150-66-5 (1E,4E)-1-(3-bromophenyl)-5-(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one 
• 1391150-64-3 (1E,4E)-1-(3-bromo-4-methoxyphenyl)-5-(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one 
• 1391150-50-7 1-(3-bromo-4-methoxyphenyl)-5-(3-hydroxy-4-methoxyphenyl)pentan-3-one 
• 1391150-52-9 1-(3-bromophenyl)-5-(3-hydroxy-4-methoxyphenyl)pentan-3-one 
• 1391150-54-1 1-(4-bromophenyl)-5-(3-hydroxy-4-methoxyphenyl)pentan-3-one 
• 1391150-55-2 1-(2-bromophenyl)-5-(3-hydroxy-4-methoxyphenyl)pentan-3-one 
• 1391150-56-3 5-(5-(3-bromo-4-methoxyphenyl)-3-hydroxypentyl)-2-methoxyphenol 
• 1391150-57-4 5-(5-(3-bromophenyl)-3-hydroxypentyl)-2-methoxyphenol 
• 1391150-58-5 5-(5-(4-bromophenyl)-3-hydroxypentyl)-2-methoxyphenol 
• 1391150-68-7 (1E,4E)-1-(4-bromophenyl)-5-(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one 
• 1391150-69-8 (1E,4E)-1-(2-bromophenyl)-5-(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one 
• 1612860-90-8 1-(3-hydroxy-4-methoxyphenyl)-7-(3-hydroxyphenyl)-1,4,6-heptatrien-3-one 
• 33187-34-7 4-(3-hydroxy-4-methoxyphenyl)hexahydro-1H-quinolizin-2(6H)-one 

Relevant academic research and scientific papers

Design, green synthesis, antioxidant activity screening, and evaluation of protective effect on cerebral ischemia reperfusion injury of novel monoenone monocarbonyl curcumin analogs

Antioxidants with high efficacy and low toxicity have the potential to treat cerebral ischemia reperfusion injury (CIRI). Dienone monocarbonyl curcumin analogs (DMCA) capable of overcoming the instability and pharmacokinetic defects of curcumin possess notable antioxidant activity but are found to be significantly toxic. In this study, a novel skeleton of the monoenone monocarbonyl curcumin analogue sAc possessing reduced toxicity and improved stability was designed on the basis of the DMCA skeleton. Moreover, 32 sAc analogs were obtained by applying a green, simple, and economical synthetic method. Multiple sAc analogs with an antioxidant protective effect in PC12 cells were screened using an H2O2-induced oxidative stress damage model, and quantitative evaluation of structure–activity relationship (QSAR) model with regression coefficient of R2 = 0.918921 was built through random forest algorithm (RF). Among these compounds, the optimally active compound sAc15 elicited a potent protective effect on cell growth of PC12 cells by effectively eliminating ROS generation in response to oxidative stress injury by activating the Nrf2/HO-1 antioxidant signaling pathway. In addition, sAc15 exhibited good protection against CIRI in the mice middle cerebral artery occlusion (MCAO) model. In this paper, we provide a novel class of antioxidants and a potential compound for stroke treatment.

Benzylideneacetone Derivatives Inhibit Osteoclastogenesis and Activate Osteoblastogenesis Independently Based on Specific Structure-Activity Relationship

(E)-3,4-Dihydroxybenzylideneacetone (compound 1) inhibited receptor activator of NF-κB ligand-induced osteoclastogenesis of C57BL/6 bone marrow monocyte/macrophages with IC50 of 7.8 μM (IC50 of alendronate, 3.7 μM) while stimulating the differentiation of MC3T3-E1 osteoblastic cells, accompanied by the induction of Runt-related transcription factor 2, alkaline phosphatase, and osteocalcin. (E)-4-(3-Hydroxy-4-methoxyphenyl)-3-buten-2-one (compound 2c) showed a dramatically increased osteoclast-inhibitory potency with IC50 of 0.11 μM while sustaining osteoblast-stimulatory activity. (E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one (compound 2g) stimulated alkaline phosphatase production 2-fold at 50 μM without changing osteoclast-inhibitory activity, compared with compound 1. Oral administration of compounds 1, 2c, and 2g prevented ovariectomy-induced osteoporosis in ddY mice to a degree proportional to their osteoclastogenesis-inhibitory potencies. The administration of 1 (mg/kg)/d compound 2c ameliorated histomorphometry of osteoporotic bone to a degree comparable with 10 (mg/kg)/d alendronate. Conclusively, the in vitro capacity of a few benzylideneacetone derivatives to inhibit osteoclastogenesis supported by independent osteoblastogenesis activation was convincingly reflected in in vivo management of osteoporosis, suggesting a potential novel therapeutics for osteopenic diseases.

Synthesis, cytotoxicity against human oral cancer KB cells and structure-activity relationship studies of trienone analogues of curcuminoids

A general method for the synthesis of substituted (1E,4E,6E)-1,7- diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9-20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure-activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study.

Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling

Microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling is described. Using the optimized conditions, a panel of macrocycles, with different substitution patterns, ring sizes, and linkers, has been successfully synthesized using microwave irradiation. To the best of our knowledge, this work represents the first examples of the microwave-assisted synthesis of macrocyclic diaryl ethers via intramolecular and/or bimolecular Ullmann coupling.

Dehydrozingerone, a structural analogue of curcumin, induces cell-cycle arrest at the G2/M phase and accumulates intracellular ROS in HT-29 human colon cancer cells

Dehydrozingerone (1) is a pungent constituent present in the rhizomes of ginger (Zingiber officinale) and belongs structurally to the vanillyl ketone class. It is a representative of half the chemical structure of curcumin (2), which is an antioxidative yellow pigment obtained from the rhizomes of turmeric (Curcuma longa). Numerous studies have suggested that 2 is a promising phytochemical for the inhibition of malignant tumors, including colon cancer. On the other hand, there have been few studies on the potential antineoplastic properties of 1, and its mode of action based on a molecular mechanism is little known. Therefore, the antiproliferative effects of 1 were evaluated against HT-29 human colon cancer cells, and it was found that 1 dose-dependently inhibited growth at the G2/M phase with up-regulation of p21. Dehydrozingerone additionally led to the accumulation of intracellular ROS, although most radical scavengers could not clearly repress the cell-cycle arrest at the G2/M phase. Furthermore, two synthetic isomers of 1 (iso-dehydrozingerone, 3, and ortho-dehydrozingerone, 4) were also examined. On comparing of their activities, accumulation of intracellular ROS was found to be interrelated with growth-inhibitory effects. These results suggest that analogues of 1 may be potential chemotherapeutic agents for colon cancer.

ARYLAMINE KETONES, THEIR PREPARATION METHODS, THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USE

Disclosed Arylamine ketones of formula (I), their preparation methods, the pharmaceutical compositions containing them and their use in preventing and/or treating the diseases related to the plaque-activating factors, especially in anti-inflammation and immunization, more especially in the treatment of the acute or chronic inflammation, such as, osteoarthritis, oarthritis deformans, etc..

Anti-tumor agents 255: Novel glycyrrhetinic acid-dehydrozingerone conjugates as cytotoxic agents

Esterification of glycyrrhetinic acid (GA) with dehydrozingerone (DZ) resulted in a novel cytotoxic GA-DZ conjugate. Based on this exciting finding, we conjugated eleven different DZ analogs with GA or other triterpenoids, including oleanoic acid (OA) or ursolic acid (UA). In an in vitro anti-cancer assay using nine different human tumor cell lines, most of the GA-DZ conjugates showed significant potency. Particularly, compounds 5, 29, and 30 showed significant cytotoxic effects against LN-Cap, 1A9, and KB cells with ED50 values of 0.6, 0.8, and 0.9 μM, respectively. Similar conjugates between DZ and OA or UA were inactive suggesting that the GA component is critical for activity. Notably, although GA-DZ conjugates showed potent cytotoxic activity, the individual components (GA and DZ analogs) were inactive. Thus, GA-DZ conjugates are new chemical entities and represent interesting hits for anti-cancer drug discovery and development.

Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents

Twenty-eight compounds related to dehydrozingerone (1), isoeugenol (3), and 2-hydroxychalcone (4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR (a multidrug-resistant derivative), and A549 cell lines. In particular, chalcone 15 showed significant cytotoxic activity against the A549 cell line with an IC50 value of 0.6 μg/mL. Furthermore, dehydrozingerone analogue 11 and chalcones 16 and 17 showed significant and similar cytotoxic activity against both KB (IC50 values of 2.0, 1.0, and 2.0 μg/mL, respectively) and KB-VCR (IC50 values of 1.9, 1.0, and 2.0 μ/mL, respectively) cells, suggesting that they are not substrates for the P-glycoprotein drug efflux pump.

Synthesis and cell growth inhibitory properties of substituted (E)-1-phenylbut-1-en-3-ones

A series of (E)-1-phenylbut-1-en-3-ones, based on the naturally occurring (E)-1-(4'-hydroxyphenyl)but-1-en-3-one [IC50 (K562) 60 μM], was synthesised and screened for cytotoxic activity against the K562 human leukaemia cell line. (E)-1-(Pentafluorophenyl)but-1-en-3-one [IC50 (K562) 1.8 μM] was found to be over 30-fold more active than 1.