16162-69-9

Usage

Type of compound

Ketone

Structure

Contains a phenyl group attached to a tetrahydropyran-2-yloxy group

Usage in organic synthesis

Building block for the synthesis of various biologically active compounds

Usage in medicinal chemistry

Building block for the synthesis of various biologically active compounds

Usage in food and cosmetic industries

Flavor and fragrance ingredient, imparting a sweet and floral scent

Therapeutic properties

Demonstrated potential therapeutic properties, making it an important target for pharmaceutical research and development

InChI:InChI=1/C13H16O3/c1-10(14)11-5-7-12(8-6-11)16-13-4-2-3-9-15-13/h5-8,13H,2-4,9H2,1H3

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 99-93-4 4-Hydroxyacetophenone 
• 121-71-1 3-Hydroxyacetophenone 
• 155853-31-9 2-methyl-2-(4-tetrahydropyran-4-yloxy)-(1,3)-dithiane 

Downstream Products

• 130600-77-0 4',3,4-tris(tetrahydropyran-2-yloxy)chalcone 
• 90548-66-6 3-Dimethylamino-2-dimethylaminomethyl-1-(4-hydroxy-phenyl)-propan-1-one; hydrobromide 
• 130600-46-3 2,2-Dimethyl-N-[2-{3-oxo-3-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-propionyl}-3-(tetrahydro-pyran-2-yloxy)-phenyl]-propionamide 
• 1027578-54-6 (E)-3-Quinolin-3-yl-1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-propenone 
• 1027524-71-5 (E)-3-Naphthalen-1-yl-1-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-propenone 

Relevant academic research and scientific papers

A versatile ruthenium catalyst for the tetrahydropyranylation of alcohols and phenols

The tetrahydropyranyl derivatives of alcohols and phenols are efficiently prepared in the presence of catalytic amounts of [Ru(CH3CN)3(triphos)](OTf)2 (triphos = CH3C(CH2PPh2)3) under mild conditions, in good to excellent yields.

Antimalarial activity of ferrocenyl chalcones

A series of ferrocenyl chalcones were synthesized and evaluated for in vitro antimalarial activity against a chloroquine-resistant strain of Plasmodium falciparum. The most active compounds were 1-(3-pyridyl)-3-ferrocenyl-2-propen-1-one (6) and 1-ferrocen

AZOLYLACRYLOYL DERIVATIVES AS THERAPEUTIC AGENTS FOR SICKLE CELL DISEASE

Azolylacryloyl derivatives with hypoxic properties are provided. The compounds have a generic formula: and are suitable for treating sickle cell disease and hypoxia-underlying diseases, e.g. hemorrhagic and traumatic shock, cardiac arrest and cardiogenic shock, traumatic brain injury, cancer, stroke, myocardial infarction, myocardial ischemia, vaso-occlusive crisis, etc.

Polymerizable compound, a liquid crystal display element and polymerizable composition

PROBLEM TO BE SOLVED: To provide a polymerizable compound having proper polymerization reactivity, high conversion rate and high solubility to a liquid crystal composition, a polymerizable composition containing the compound, a liquid crystal composite prepared from the composition and a liquid crystal display element having the composite.SOLUTION: There is provided a polymerizable compound having the following structure: (in the formula, Pand Pare a polymerizable group; rings Ato Aare 1,4-phenylene, Zand Zare a single bond or alkylene; Lto Lare a single bond; and a, b, c and d are 0 or 1.)

Novel licochalcone analogue compounds having anti-inflammatory activity

A licochalcone is known to have various biological activities. However, most licochalcones exhibit cytotoxicity. Licochalcones B and D having a common substituent in an aromatic ring B have been a target for denaturing the structure of an aromatic ring A

Synthesis of licochalcone analogues with increased anti-inflammatory activity

Licohalcones have been reported to have various biological activities. However, most of licochalcones also showed cytotoxicity even though their versitile utilities. Licochalcones B and D, which have common substituents at aromatic ring B, are targeted to

Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway

Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/β-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of β-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of β-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than 1a (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma.

Environmentally benign deprotection of dithioacetals using 30% hydrogen peroxide catalyzed by Fe(acac)3 and sodium iodide

The reaction of dithioacetals with 30% hydrogen peroxide in the presence of catalytic amounts of iron(III) acetylacetonate and sodium iodide efficiently produced the corresponding carbonyl compounds in high yields.

Design, synthesis, and in vitro hMAO-B inhibitory evaluation of some 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles

A series of 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles (3a-k and 4a-u) were designed, synthesized, and evaluated for their inhibitory efficacy towards the two hMAO isoforms. Most of the derivatives were found to be potent and selective hMAO-B inhibitors. In particular, derivative 3g showed greater hMAO-B affinity than selective inhibitor selegiline coupled with high selectivity index (SI = 145). The most selective hMAO-B inhibitor was the 3-methyl analogue 3f with an SI higher than 909.

Deprotection of dithioacetals with 30% hydrogen peroxide catalyzed by tantalum(V) chloride-sodium iodide or niobium(V) chloride-sodium iodide

The reaction of dithioacetals with 30% hydrogen peroxide in the presence of catalytic amounts of tantalum(V) and iodide ion effectively produced carbonyl compounds in high yields. Dithioacetals also can be deprotected using the niobium(V) catalyzed oxidation of iodide ion by hydrogen peroxide under mild conditions.