40815-74-5

Usage

Uses

Used in Organic Synthesis:
Ethanone, 1-[2-hydroxy-4-(2-propenyloxy)phenyl]is used as a reactive intermediate for the synthesis of various organic compounds. Its hydroxy and propenyl groups facilitate reactions that can lead to the formation of new molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
Ethanone, 1-[2-hydroxy-4-(2-propenyloxy)phenyl]is used as a building block in the development of pharmaceutical compounds. Its unique structure allows for the creation of new drug candidates that could exhibit novel therapeutic properties, potentially leading to the discovery of new treatments for various diseases.
Used in Materials Science:
Ethanone, 1-[2-hydroxy-4-(2-propenyloxy)phenyl]is used as a component in the formulation of advanced materials. Its chemical properties can contribute to the development of new materials with improved properties, such as enhanced stability, reactivity, or functionality, which can be utilized in various applications, including coatings, adhesives, or composites.

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 108-46-3 recorcinol 

Downstream Products

• 38987-00-7 2,4-dihydroxy-3-allylacetophenone 
• 92831-82-8 4-Allyloxy-2,5-dihydroxyacetophenone 
• 117705-60-9 1-(4-allyloxy-2-methoxy-phenyl)-ethanone 
• 38987-01-8 5-allyl-2,4-dihydroxyacetophenone 
• 69722-46-9 1-(4-hydroxy-benzofuran-5-yl)-ethanone 
• 521-88-0 karanjin 
• 112606-78-7 (E)-1-(4-hydroxybenzofuran-5-yl)-3-phenylprop-2-en-1-one 
• 4439-65-0 7-hydroxy-8-phenylfuro[2,3-h]benzopyran-6-one 
• 40786-69-4 1-(2,4-dihydroxy-3-propylphenyl)ethanone 
• 96566-25-5 Ro 23-3544 
• 120329-95-5 methyl (R,S)-6-acetyl-7-<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentoxy>-3,4-dihydro-2H-1-benzopyran-2-carboxylate 
• 96565-55-8 (R,S)-6-acetyl-7-<<5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyl>oxy>-3,4-dihydro-2H-H-benzopyran-2-carboxylic acid sodium salt 
• 117705-59-6 5-allyl-4-hydroxy-2-methoxyacetophenone 
• 117690-48-9 4-Butoxy-2-hydroxy-5-allylacetophenone 

Relevant academic research and scientific papers

Synthesis, molecular modelling studies of indolyl chalcone derivatives and their antimalarial activity evaluation

Twenty one chalcone derivatives were synthesized using Claisen-Schmidt condensation, their antimalarial activity against Plasmodium falciparum was determined and quantitative structure–activity relationship (QSAR) was developed. Condensation of substituted acetophenones with various aromatic aldehydes at room temperature gave chalcones in 75–96% yield. Chalcones are secondary metabolites of terrestrial plants, precursors for the biosynthesis of flavonoids and exhibit various biological activities. Antiplasmodial IC50 (half-maximal inhibitory concentration) activity of a compound against malaria parasites in?vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was Trans-3-(1H-indol-3-yl)-1-(2’-hydroxyphenyl)-2-propen-1-one(1b) with IC50 of 2.1 μM/L. Molecular mechanism was explored through in silico docking & ADMET studies for the active compounds.

Azo Dyes: New Palladium- and Copper-Catalysed Coupling Reactions on an Old Template

The elaboration of azo dyes using a variety of transition-metal-catalysed reactions (Stille, Heck, Ullmann, and Suzuki couplings) is reported. This methodology has been applied to the synthesis of functionalised coumarin azo dye conjugates, substrates which may find potential application in the development of new sensors.

Total Synthesis of Xanthoangelol B and Its Various Fragments: Toward Inhibition of Virulence Factor Production of Staphylococcus aureus

As an alternative strategy to fight antibiotic resistance, two-component systems (TCSs) have emerged as novel targets. Among TCSs, master virulence regulators that control the expression of multiple virulence factors are considered as excellent antivirulence targets. In Staphylococcus aureus, virulence factor expression is tightly regulated by a few master regulators, including the SaeRS TCS. In this study, we used a SaeRS GFP-reporter system to screen natural compound inhibitors of SaeRS, and identified xanthoangelol B 1, a prenylated chalcone from Angelica keiskei as a hit. We have synthesized 1 and its derivative PM-56 and shown that 1 and PM-56 both had excellent inhibitory potency against the SaeRS TCS, as demonstrated by various in vitro and in vivo experiments. As a mode of action, 1 and PM-56 were shown to bind directly to SaeS and inhibit its histidine kinase activity, which suggests a possibility of a broad spectrum inhibitor of histidine kinases.

Facile synthesis of vanillin-based novel bischalcones identifies one that induces apoptosis and displays synergy with Artemisinin in killing chloroquine resistant Plasmodium falciparum

The inherent affinity of natural compounds for biological receptors has been comprehensively exploited with great success for the development of many drugs, including antimalarials. Here the natural flavoring compound vanillin has been used as an economical precursor for the synthesis of a series of novel bischalcones whose in vitro antiplasmodial activities have been evaluated against erythrocytic stages of Plasmodium falciparum. Bischalcones 9, 11 and 13 showed promising antiplasmodial activity {Chloroquine (CQ) sensitive Pf3D7 IC50 (μM): 2.0, 1.5 and 2.5 respectively}but only 13 displayed potent activities also against CQ resistant PfDd2 and PfIndo strains exhibiting resistance indices of 1.4 and 1.5 respectively. IC90 (8 μM) of 13 showed killing activity against ring, trophozoite and schizont stages. Further, 13 initiated the cascade of reactions that culminates in programmed cell death of parasites including translocation of phosphatidylserine from inner to outer membrane leaflet, loss of mitochondrial membrane potential, activation of caspase like enzyme, DNA fragmentation and chromatin condensation. The combinations of 13 + Artemisinin (ART) exhibited strong synergy (ΣFIC50:0.46 to 0.58) while 13 + CQ exhibited mild synergy (ΣFIC50: 0.7 to 0.98) to mild antagonism (ΣFIC50: 1.08 to 1.23) against PfIndo. In contrast, both combinations showed marked antagonism against Pf3D7(ΣFIC50: 1.33 to 3.34). These features of apoptosis and strong synergy with Artemisinin suggest that bischalcones possess promising antimalarial drug-like properties and may also act as a good partner drugs for artemisinin based combination therapies (ACTs) against Chloroquine resistant P. falciparum.

Synthesis of 8′,11′-dihydrospiro[cyclohexane-1,2′-oxepino[2,3-: H] chromen]-4′(3′ H)-ones with ring closing metathesis as a key step

A series of novel hybrid molecular entities incorporating various spiro chromanone scaffolds onto the benzannulated oxepine core moiety were synthesised using allylation, Claisen rearrangement, Kabbe condensation and Ring Closing Metathesis (RCM) as a key step. During the synthesis we found that the nitrogen functionality in the substrate influences significantly the catalyst load due to electronic effects. Several iterations have been carried out to achieve complete conversion to products 6a-6e.

Facile one-pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers under mild conditions

We report here the facile, room temperature, catalyst free, one pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers. Anhydrous potassium carbonate (K2CO3) as a mild base along with dimethyl sulfoxide gener

Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives: Pyrano[3,2-c]chromene-2,5-diones

A series of novel fused coumarin analogues pyrano[3,2-c]chromene-2,5-diones have been synthesized through an optimized microwave-assisted protocol. All target compounds were tested and evaluated for their antifungal activity against Botrytis cinerea, Colletotrichum copsica, Alternaria solani, Gibberella zeae and Rhizoctorzia solani. The bioassay results indicated that some of the compounds exhibited potent antifungal activities at concentration less than 50 ppm. For the compounds 5d, 6c and 7b, EC50 values against B. cinerea were as low as 0.141, 0.082 and 0.091 μM, respectively, which represents better antifungal activity than that of the commonly used fungicide Azoxystrobin. Compounds 5d (57%) and 6c (55%) also exhibited more effective control than Azoxystrobin (44%) against Colletotrichum capsica.

Natural product Hirtellanine B and its derivatives in the preparation process for the preparation of medicine for treating tumor with the application of the

The present invention provides a preparation method of a natural product Hirtellanine B, wherein 2,4,6-trihydroxyacetophenone is adopted as a raw material, and steps of compound a preparation, compound b preparation, compound c preparation, compound d preparation, compound e preparation, compound f preparation, compound g preparation, and the like are performed to prepare the natural product Hirtellanine B. According to the present invention, biological activity screening is performed on Hirtellanine B and 14 Hirtellanine B derivatives, and results show that the natural product Hirtellanine B can inhibit proliferations of Jurkat cells, Raji cells and K562 cells, and the compounds provide a certain inhibition activity for tumor cells. The method has characteristics of easily available raw material, high reaction yield and reasonable operation, and is suitable for industrial production. The Hirtellanine B and the derivatives thereof can be used for preparing tumor treatment drugs, and have great clinical values. The natural product Hirtellanine B preparation method reaction formulas are as the follows.

Microwave-promoted Synthesis of Novel Fused Osthole Analogues

Osthole is a natural coumarin derivative and has a broad scope of biological activities. Two series of novel fused osthole analogues were designed, and synthesized through a highly efficient microwave-promoted synthetic protocol via the reaction of 4-hydroxycoumarins and β-ketoesters. The reaction conditions including solvent, catalyst, microwave power and irradiation time were also optimized. The pyrano[3,2-c]chromene-2,5-diones and furo[3,2-c]coumarins were obtained through two distinct intramolecular cyclization processes, and the proposed mechanism was also discussed.

Chemical synthesis, docking studies and biological effects of functionalized 1,3-diaryl-2-propen-1-ones on human colon cancer cells

A series of 1, 3-diaryl-2-propen-1-ones was synthesised in order to obtain a new type of anticancer drug, designed with hybrid features to inhibit colon cancer activated receptor. Based on computational modelling and docking studies, potential inhibitors were synthesised and their biological activity evaluated. The structures of newly synthesized compounds were confirmed by1HNMR,13CNMR and Mass spectrometry. All analogues were evaluated for in vitro cytotoxicity against human colon (caco-2) cancer cell lines. Compounds 1b, 1f-1h, and 2i showed significant cytotoxicity. Chalcones 1b, 1f and 1g were identified as the most potent and selective anticancer agents with IC50 values 1 μg/mL and 1.5 μg/mL, against caco-2 cell line, respectively. In conclusion, this finding confirms the suitability of indolyl chalcone analogues as candidates for further investigation towards the management of colon cancer related diseases.