22479-95-4

Usage

Chemical Properties

white solid

Synthesis Reference(s)

Tetrahedron Letters, 18, p. 611, 1977 DOI: 10.1016/S0040-4039(01)92706-6

InChI:InChI=1/C10H10O5/c1-14-9(12)7-4-3-6(11)5-8(7)10(13)15-2/h3-5,11H,1-2H3

Upstream product

• 67-56-1 methanol 
• 610-35-5 4-hydroxyphthalic acid 
• 54125-02-9 danishefsky's diene 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 89-08-7 4-sulfophthalic acid 
• 483-84-1 8-hydroxy-5,7-dinitro-2-naphthalenesulfonic acid 
• 131-11-3 phthalic acid dimethyl ester 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 59414-23-2 1-methoxy-3-<(trimethylsilyl)oxy>01,3-butadiene 

Downstream Products

• 22895-19-8 dimethyl 4-methoxyphtalate 
• 5840-67-5 4-Benzyloxy-phthalsaeure-dimethylester 
• 332370-51-1 4-(2-nitrophenoxy)phthalic acid dimethyl ester 
• 1001327-32-7 C₁₃H₁₂N₂O₅S 
• 110300-54-4 dimethyl 4-(β-phenoxyethoxy)phthalate 
• 142671-51-0 dimethyl 4-hydroxy-3-nitrophthalate 
• 142671-50-9 dimethyl 4-hydroxy-5-nitrophthalate 
• 65687-25-4 dimethyl 4-(3-phenoxypropoxy)phthalate 
• 203729-13-9 dimethyl 3,5-dibromo-4-hydroxyphthalate 
• 268234-31-7 dimethyl 4-[3-((E)-1,5-diethyltriethylsilanyloxyhept-1-enyl)phenylmethoxy]phthalate 
• 341555-89-3 dimethyl 4-[5-((E)-1,5-diethyl-5-triethylsilanyloxyhept-1-enyl)-3-thienylmethoxy]phthalate 
• 341006-33-5 Dimethyl 4-[4'-(2-ethyl-[1,3]dioxolan-2-yl)-2'-methylbiphenyl-3-ylmethoxy]phthalate 
• 1072880-92-2 dimethyl 4-(cyclohexylcarbamoyloxy)phthalate 
• 1547162-41-3 5-hydroxypomalidomide 

Relevant academic research and scientific papers

Product-oriented chemical surface modification of a levansucrase (SacB): Via an ene-type reaction

Carbohydrate processing enzymes are sophisticated tools of living systems that have evolved to execute specific reactions on sugars. Here we present for the first time the site-selective chemical modification of exposed tyrosine residues in SacB, a levansucrase from Bacillus megaterium (Bm-LS) for enzyme engineering purposes via an ene-type reaction. Bm-LS is unable to sustain the synthesis of high molecular weight (HMW) levan (a fructose polymer) due to protein-oligosaccharide dissociation events occurring at an early stage during polymer elongation. We switched the catalyst from levan-like oligosaccharide synthesis to the efficient production of a HMW fructan polymer through the covalent addition of a flexible chemical side-chain that fluctuates over the central binding cavity of the enzyme preventing premature oligosaccharide disengagement.

Crystal growth, structure, and polymorphic behavior of an ionic liquid: Phthalate derivative of N -Butyl, N -methylimidazolium Hexafluorophosphate

After the multistep synthesis of an original imidazolium hexafluorophosphate ionic liquid, [pbmim][PF6], two polymorphic forms were isolated from methanolic solution and characterized by XRPD, DSC, and Raman spectroscopy. Stable Form A (mp 90.3 °C) was obtained by conventional crystallization at a moderate cooling rate (10 K/min) was applied. Structural analyses carried out by using single-crystal (Form A) and powder (Form B) X-ray diffraction revealed a rotational disorder of anionic octahedrons and, more interestingly, large conformational differences between cationic moieties caused by their molecular flexibility. Crystal growth of [pbmim][PF6] (Form A) in methanol often leads to numerous crystal defects and revealed that most of them consist of liquid inclusions. The supersaturation ratio (β) appeared to be the predominant factor influencing the crystal growth behavior under isothermal and stagnant conditions. At low β values, a morphological transition from rod-shaped crystals to platelets was observed, presumably caused by a change in the growth mechanism of specific faces. Using high β values promotes either the formation of microscopic (5 μm) liquid inclusions that become easily detectable upon heating or the appearance of macroscopic inclusions with an hourglass shape.

Structural essentials of xenoestrogen dialkyl phthalates to bind to the estrogen receptors

Xenoestrogen dialkyl phthalates, C6H4(COOCnHm)2, lack the phenolic hydroxyl group that is an essential structural component of the steroid A ring of 17β-estradiol. In order to examine whether dialkyl phthalates imitate the steroid structure, we have synthesized a series of 4-hydroxyl derivatives of dialkyl phthalates. The compounds were examined for their ability to displace [3H]17β-estradiol from the recombinant human estrogen receptor, which was expressed on Sf9 cells using the vaculovirus expression system. Dialkyl 4-hydroxyl phthalates were found to exhibit several-fold higher binding affinities compared to phthalates without the 4-hydroxyl group. From the analyses of receptor binding modes of dialkyl phthalates with and without the 4-hydroxyl group, it was deduced that the phthalic benzene ring mimics the steroid A ring. A biphasic binding curve observed for dicyclohexyl phthalate was also depicted by its 4-hydroxyl derivative, but it increased binding affinity only at the high affinity binding site. These data suggest that the phthalate benzene moiety recognizes the core of the estrogen receptor binding site and the hydrophobic interaction of the dialkyl moiety substantiates the binding characteristics of the phthalates. The present data indicate that even chemicals with slight structural analogy and weak receptor affinity can perturb the endocrine system when administered in high concentrations.

BIFUNCTIONAL COMPOUNDS FOR THE TREATMENT OF CANCER

The invention provides bifunctional compounds of formula (I) or a pharmaceutically acceptable salt thereof. Formula (I). The compounds cause the degradation of SMARCA2 via the targeted ubiquination of SMARCA2 protein and subsequent proteasomal degradation and are thus useful for the treatment of cancer. The targeting ligand is of formula (TL).

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand

The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.

NOVEL BROMINATED FURANONE DERIVATIVE, METHOD FOR PREPARING SAME, AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a novel brominated furanone derivative, a method for preparing the same, and a pharmaceutical composition containing the same as an active ingredient, wherein the novel brominated furanone derivative or a pharmaceutically acceptable 5 salt thereof according to the present invention exhibits a quorum sensing inhibitory activity of bacteria and also can effectively inhibit the formation of biofilm of bacteria, and thus can be used as a pharmaceutical composition containing the same as an active ingredient, thereby having an effect of being useful, 10 for example, for periodontal diseases such as gingivitis and periodontitis, oral diseases, and the like.

Automated on-line monitoring of the TiO2-based photocatalytic degradation of dimethyl phthalate and diethyl phthalate

A fully automated on-line system for monitoring the TiO2-based photocatalytic degradation of dimethyl phthalate (DMP) and diethyl phthalate (DEP) using sequential injection analysis (SIA) coupled to liquid chromatography (LC) with UV detection was proposed. The effects of the type of catalyst (sol-gel, Degussa P25 and Hombikat), the amount of catalyst (0.5, 1.0 and 1.5 g L-1), and the solution pH (4, 7 and 10) were evaluated through a three-level fractional factorial design (FFD) to verify the influence of the factors on the response variable (degradation efficiency, %). As a result of FFD evaluation, the main factor that influences the process is the type of catalyst. Degradation percentages close to 100% under UV-vis radiation were reached using the two commercial TiO2 materials, which present mixed phases (anatase/rutile), Degussa P25 (82%/18%) and Hombikat (76%/24%). 60% degradation was obtained using the laboratory-made pure anatase crystalline TiO2 phase. The pH and amount of catalyst showed minimum significant effect on the degradation efficiencies of DMP and DEP. Greater degradation efficiency was achieved using Degussa P25 at pH 10 with 1.5 g L-1 catalyst dosage. Under these conditions, complete degradation and 92% mineralization were achieved after 300 min of reaction. Additionally, a drastic decrease in the concentration of BOD5 and COD was observed, which results in significant enhancement of their biodegradability obtaining a BOD5/COD index of 0.66 after the photocatalytic treatment. The main intermediate products found were dimethyl 4-hydroxyphthalate, 4-hydroxy-diethyl phthalate, phthalic acid and phthalic anhydride indicating that the photocatalytic degradation pathway involved the hydrolysis reaction of the aliphatic chain and hydroxylation of the aromatic ring, obtaining products with lower toxicity than the initial molecules.

New bicyclic brominated furanones as potent autoinducer-2 quorum-sensing inhibitors against bacterial biofilm formation

Bacterial behaviors such as virulence factor secretion and biofilm formation are critical for survival, and are effectively regulated through quorum sensing, a mechanism of intra- and interspecies communication in response to changes in cell density and species complexity. Many bacterial species colonize host tissues and form a defensive structure called a biofilm, which can be the basis of inflammatory diseases. Periodontitis, a chronic inflammatory disease affecting the periodontium, is caused by subgingival biofilms related to periodontopathogens. In particular, Fusobacterium nucleatum is a major co-aggregation bridge organism in the formation and growth of subgingival biofilms, linking the early and late colonizers in periodontal biofilms. According to our previous study, the intergeneric quorum-sensing signal molecule autoinducer-2 (AI-2) of F. nucleatum plays a key role in intra- and interspecies interactions of periodontopathogens, and may be a good target for periodontal biofilm inhibition. Recently, brominated furanones produced by the macroalga Delisea pulchra were shown to inhibit biofilm formation via AI-2, and have been investigated toward the goal of increasing the inhibition effect. In this study, we describe the synthesis of new bromofuranone analogs, i.e., 3-(dibromomethylene)isobenzofuran-1(3H)-one derivatives, and demonstrate their inhibitory activities against biofilm formation by periodontopathogens, including F. nucleatum, Porphyromonas gingivalis, and Tannerella forsythia.

NOVEL PRODRUGS OF DITHIOL MUCOLYTIC AGENTS

Provided are mucolytic compounds that are more effective, and/or absorbed less rapidly from mucosal surfaces, and/or are better tolerated as compared to N-acetylcysteine (NAC) and DTT. The compounds are represented by compounds of Formula I which embrace structures (la)-(Ib), where the structural variables are as defined herein.