35310-75-9

Usage

Preparation

Obtained by reaction of acetic anhydride with o-bromoanisole in the presence of lithium perchlorate at 100° for 5 h (99%).

InChI:InChI=1/C9H9BrO2/c1-6(11)7-3-4-9(12-2)8(10)5-7/h3-5H,1-2H3

Upstream product

• 578-57-4 2-bromoanisole 
• 75-36-5 acetyl chloride 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 108-24-7 acetic anhydride 
• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 64-19-7 acetic acid 
• 95-56-7 2-hydroxybromobenzene 
• 67-56-1 methanol 
• 3114-30-5 1-(3,4-dibromophenyl)ethan-1-one 
• 1515-95-3 p-ethylanisole 
• 188726-01-4 3-Cyano-4-(trifluoromethoxy)acetophenone 
• 50870-41-2 4,4,8,8-Tetrabrom-1,5-dimethoxy-tricyclo-<5.1.0.0.3.5>-octan 
• 94670-25-4 3-bromo-α-methyl-4-methoxybenzenemethanol 

Downstream Products

• 875817-19-9 1-(4-methoxy-3-phenoxy-phenyl)-ethanone 
• 6096-83-9 2?bromo?1?(3?bromo?4?methoxyphenyl)ethan?1?one 
• 99-58-1 3-bromo-4-methoxybenzoic acid 
• 81224-34-2 2-(3-bromo-4-methoxyphenyl)-2-methyl-1,3-dioxolane 
• 81224-38-6 methoxy-4 acetyl-7 indole 
• 113016-89-0 5‐acetyl‐2‐methoxybenzonitrile 
• 1087764-78-0 3'-bromo-4'-methoxychalcone 
• 884501-83-1 1-(3-bromo-4-methoxyphenyl)-3-(2-methoxypyridin-3-yl)propane-1,3-dione 
• 745078-99-3 methyl 5-(3-bromo-4-methoxyphenyl)isoxazole-3-carboxylate 

Relevant academic research and scientific papers

Synthesis of 3-bromo-5-(2-ethylimidazo[1, 2-a]pyridine-3-carbonyl)-2-hydroxybenzonitrile

The invention discloses a synthetic method of 3-bromo-5-(2-ethylimidazo[1,2-a]pyridine-3-carbonyl)-2-hydroxybenzonitrile, particularly relates to a synthetic method of a compound shown as a formula (III), and particularly relates to a step A or a step B;

Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors

Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. The most potent compound 22 (LXQ46) inhibited PTP1B with an IC50 value of 0.190 μM, and showed remarkable selectivity over other protein tyrosine phosphatases (PTPs, 20–200 folds). In the SPR study, increasing concentrations of compound 22 led to concentration-dependent increases in binding responses, indicating that compound 22 could bind to the surface of PTP1B via noncovalent means. By treating insulin-resistant C2C12 myotubes with compound 22, enhanced insulin and leptin signaling pathways were observed. Long-term oral administration of compound 22 reduced the blood glucose level of diabetic BKS db mice. The glucose tolerance tests (OGTT) and insulin tolerance tests (ITT) in BKS db mice showed that oral administration of compound 22 could increase insulin sensitivity. In addition, long-term oral administration of compound 22 could protect mice from obesity, which was not the result of toxicity. Our pharmacokinetics results from the rat-based assays showed that orally administered compound 22 was absorbed rapidly from the gastrointestinal tract, extensively distributed to the tissues, and rapidly eliminated from the body. All these results indicate that compound 22 could serve as a qualified agent to treat type II diabetes.

Aromatic Halogenation Using N-Halosuccinimide and PhSSiMe3 or PhSSPh

We developed a mild aromatic halogenation reaction using a combination of N-halosuccinimide and PhSSiMe3 or PhSSPh. Less reactive aromatic compounds, such as methyl 4-methoxybenzoate, were brominated with PhSSiMe3 or PhSSPh and N-bromosuccinimide in high yields. No reaction was observed in the absence of PhSSiMe3 or PhSSPh. This method is also applicable to chlorination reactions using N-chlorosuccinimide and PhSSPh.

Synthesis method for aromatic ring bromination of acetophenones derivative

The invention relates to a synthesis method for aromatic ring bromination of an acetophenones derivative, and belongs to the technical field of organic synthesis. The synthesis method consists of twokinds of synthesis methods: method A, adding the acetophenone derivative into a first oxidizing agent and stirring to form a suspension system, controlling the temperature of the suspension system tobe 10-50 DEG C, adding a first reducing agent or a second reducing agent, stirring and reacting for 2-20 h, and performing aftertreatment after the reaction is completed to obtain the aromatic ring brominated acetophenone derivative; method B, adding the acetophenone derivative into the second reducing agent and stirring to form a suspension system, controlling the temperature of the suspension system to be 10-50 DEG C, then adding a second oxidizing agent or the first oxidizing agent, stirring and reacting for 2-20 h, and performing aftertreatment after the reaction is completed to obtain thearomatic ring brominated acetophenone derivative. According to the synthesis method provided by the invention, an inorganic and non-toxic bromination reagent is used, water is used as a reaction solvent, the prepared product is mutually incompatible with water, so that separation and the aftertreatment are convenient to perform, therefore, the synthesis method of the invention is applicable to large-scale industrial production of intermediate products for aromatic ring bromination of the acetophenones derivative.

SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF NUCLEASES

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

Synthesis and catalytic reactivity in Friedel–Crafts acylations of monobridged bis(cyclopentadienyl)molybdenum(I) carbonyl complexes

When the monobridged biscyclopentadienes (C5H5)R(C5H5) [R = C(CH3)2 (1), Si(CH3)2 (2), C(CH2)5 (3)] reacted with Mo(CO)6 in refluxing xylene, the corresponding complexes [(η5-C5H4)2R][Mo(CO)3]2 [R = C(CH3)2 (4), Si(CH3)2 (5), C(CH2)5 (6)] were obtained. These complexes were separated by chromatography and characterized by elemental analysis, IR, and 1H NMR spectroscopy. The molecular structures of 4 and 5 were determined by X-ray diffraction analysis. Friedel–Crafts acylation reactions of anisole derivatives with aromatic or aliphatic acyl chlorides catalyzed by complexes 4–6 showed that all of these monobridged bis(cyclopentadienyl)molybdenum carbonyl complexes have catalytic activity.

Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide

Although iodine-catalyzed reaction has rapid advances in recent years, examples on iodine-catalyzed bromination are rare and the mechanism of these reactions remains unclear. Herein, we reported an I2-catalyzed aromatic bromination of aryl ethers by NBS and presented the details of the mechanistic study including kinetic study and the study of kinetic isotope effects. The study revealed that the reaction was actually catalyzed by IBr formed in the induction period, and the rate-determining step was the HBr-elimination of the Wheland intermediate assisted by IBr.

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N -Bromosuccinimide and I2-Aqueous NH3

A variety of ethylarenes were converted into the corresponding primary aromatic amides in good yields via treatment with N-bromosuccinimide in the presence of a catalytic amount of 2,2′-azobis(isobutyronitrile) in a mixture of ethyl acetate and water, acetonitrile and water, or chloroform and water, followed by reaction with molecular iodine and aq NH3 in one pot. It was found that aryl α-bromomethyl ketones and/or aryl methyl ketones were formed at the first reaction step and their iodoform-type reaction occurred at the second reaction step to provide primary aromatic amides. The present reaction is a useful and practical transition-metal-free method for the preparation of primary aromatic amides from ethylarenes. (Chemical Equation Presented).

Synthesis, biological evaluation and molecular modeling studies of psammaplin A and its analogs as potent histone deacetylases inhibitors and cytotoxic agents

In this study, a concise synthetic method of psammaplin A was achieved from 3-bromo-4-hydroxybenzaldahyde and hydantoin through a four-step synthesis via Knoevenagel condensation, hydrolysis, oximation and amidation in 37% overall yield. A collection of novel psammaplin A analogs focused on the variations of substituents at the benzene ring and modifications at the oxime moiety were synthesized. Among all the synthesized compounds, 5d and 5e showed better HDAC inhibition than psammaplin A and comparable cytotoxicity against four cancer cell lines (PC-3, MCF-7, A549 and HL-60). Molecular docking and dynamics simulation revealed that (i) hydrogen atom of the oxime group interacts with Asp99 of HDAC1 through a water bridged hydrogen bond and (ii) a hydroxyl group is optimal attached on the para-position of benzene, interacting with Glu203 at the entrance to the active site tunnel.

Aggregation-induced emission enhancement in halochalcones

A family of push-pull fluorophores, consisting of a chalcone core decorated with electron-donating substituents and halogen atoms, was designed and synthesized. Luminescence studies were performed in solution, aggregate form and in the solid state. Although some compounds are only weakly fluorescent in solution, all are emissive in the solid state showing aggregation-induced emission enhancement. In the crystalline state, the halogen atoms are not involved in halogen bonds but their presence strongly influences the aggregation-induced emission properties of the fluorophores.