38987-00-7

Usage

Preparation

Preparation by thermal Claisen rearrangement of 4-(allyloxy)-2-hydroxyacetophenone without solvent at 200–210° (85%).

Upstream product

• 40815-74-5 4-allyloxy-2-hydroxyacetophenone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Downstream Products

• 63455-98-1 8-allyl-7-hydroxy-2-phenyl-chromen-4-one 
• 61270-23-3 1-[3-Allyl-4-(5-bromo-pentyloxy)-2-hydroxy-phenyl]-ethanone 
• 118683-90-2 methyl 4-<(4-acetyl-3-hydroxy-2-prop-2-enylphenoxy)methyl>-3-methoxybenzoate 
• 106627-28-5 6-(4-Acetyl-2-allyl-3-hydroxy-phenoxy)-hexanoic acid benzhydryl ester 
• 40786-69-4 1-(2,4-dihydroxy-3-propylphenyl)ethanone 
• 149810-10-6 2'-hydroxy-3'-allyl-4'-(acetoxy)acetophenone 
• 69722-46-9 1-(4-hydroxy-benzofuran-5-yl)-ethanone 
• 92518-37-1 6-(4-Acetyl-3-hydroxy-2-allylphenoxy)-hexanoic acid 
• 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 
• 691008-31-8 2-phenyl-8-(prop-2-en-1-yl)-7-(prop-2-en-1-yloxy)-4H-1-benzopyran-4-one 
• 119517-23-6 1-(3-allyl-2,4-dimethoxy-phenyl)-ethanone 
• 40785-92-0 3-(4-acetyl-2-allyl-3-hydroxyphenoxy)-1,2-epoxypropane 

Relevant academic research and scientific papers

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.

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.

Regioselectivity in aromatic Claisen rearrangements

Theoretical calculations and the isomeric product composition for a series of eight meta-substituted allyl aryl ethers confirm the reliability of a new 1H NMR methodology used to predict aromatic Claisen regioselectivity from ground-state confo

Synthesis of the leukotriene antagonist ablukast

An efficient synthesis of the leukotriene antagonist ablukast (5) has been achieved starting from 2,4-dihydroxyacetophenone. The latter, on a Claisen condensation with ethyl oxalate, followed by hydrogenation, gave the chromane ester 7, which was subjected to a Fries rearrangement (AcOH/BF3·OEt2) and the product, after transesterification with methanol, was alkylated with 5-bromo-1-pentanyl acetate to afford the acetate 9. A novel methanolysis of 9 with methanol in the presence of tetra-n-butylammonium hydroxide followed by mesylation of the derived alcohol furnished the mesylate 10. Alkylation of the acetophenone derivative 16 with 10 using K2CO3 in the presence of tris(3,6-dioxaheptyl)amine and saponification gave 5.

STEREOSELECTIVE SYNTHESIS OF LEUKOTRIENE ANTAGONISTS

The present invention relates to a stereo-selective synthesis of leukotriene antagonists. More particularly, this invention relates to the stereo-selective synthesis of (βS,γR) and (βR,γS)-4-((3-(4-acetyl-3-hydroxy-2-propyl(phenoxy)propyl)-thio-γ-hydroxy-

Stereoselective synthesis of leukotriene antagonists

The present invention relates to a stereo-selective synthesis of leukotriene antagonists. More particularly, this invention relates to the stereo-selective synthesis of (βS,γR) and (βR,γS)--4-((3-(4-acetyl-3-hydroxy-2-propyl(phenoxy)propyl)-thio)-γ-hydroxy-β-methylbenzenebutanoic acid, and related compounds. These compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders, inflammation and pain in mammals, especially humans. The compounds are also useful for inducing cytoprotection in mammals, especially humans.

Novel benzopyran derivatives

7-[3-(4-Acetyl-3-hydroxy-6-iodo-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylic acid and its pharmaceutically acceptable salts are employed as antagonists of SRS-A (the slow reacting substance of anaphylaxis) in the treatmen