35458-39-0

Usage

Uses

Used in Medicinal Chemistry and Drug Development:
4-BROMO-2,5-DIMETHOXYBENZOIC ACID is used as a pharmaceutical candidate for its anti-inflammatory and anticoagulant activities, as well as its potential in the treatment of heart and vascular diseases. Its promising biological properties make it a valuable compound for the development of new therapeutic agents.
Used in Organic Synthesis and Materials Science:
4-BROMO-2,5-DIMETHOXYBENZOIC ACID is also utilized in organic synthesis and materials science, where its unique chemical structure and properties can contribute to the creation of new materials and compounds with specific applications.

InChI:InChI=1/C9H9BrO4/c1-13-7-4-6(10)8(14-2)3-5(7)9(11)12/h3-4H,1-2H3,(H,11,12)

Upstream product

• 13321-74-9 1-bromo-2,5-dimethoxy-4-methylbenzene 
• 31558-41-5 4-bromo-2,5-dimethoxybenzaldehyde 
• 124-38-9 carbon dioxide 
• 2674-34-2 1,4-dibromo-2,5-dimethoxybenzene 
• 67289-05-8 2-bromo-5-methylbenzene-1,4-diol 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 150-78-7 1,4-dimethoxybezene 

Downstream Products

• 873420-96-3 4-bromo-2,5-dihydroxybenzoic acid 
• 98545-68-7 2-bromo-1,4-dimethoxy-5-nitrobenzene 
• 87050-61-1 (4-bromo-2,5-dimethoxy-phenyl)-methanol 

Relevant academic research and scientific papers

Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin α

The anticancer natural product simaomicin α has been synthesized. Asymmetric synthesis allowed the assignment of absolute stereochemistry. The enantiomer of the naturally occurring substance shows potent cytotoxicity towards Gram-positive bacteria and human cancer cells. Bn=benzyl, BOM=benzyloxymethyl. Copyright

Peptide-Catalyzed Fragment Couplings that Form Axially Chiral Non-C2-Symmetric Biaryls

We have demonstrated that small, modular, tetrameric peptides featuring the Lewis-basic residue β-dimethylaminoalanine (Dmaa) are capable of atroposelectively coupling naphthols and ester-bearing quinones to yield non-C2-symmetric BINOL-type scaffolds with good yields and enantioselectivity. The study culminates in the asymmetric synthesis of backbone-substituted scaffolds similar to 3,3′-disubstituted BINOLs, such as (R)-TRIP, with good (94:6 e.r.) to excellent (>99.9:0.1 e.r.) enantioselectivity after recrystallization, and a diastereoselective net arylation of the minimally modified nonsteroidal anti-inflammatory drug (NSAID) naproxen.

Process Development and Scale-up of Fully Synthetic Tetracycline TP-2758: A Potent Antibacterial Agent with Excellent Oral Bioavailability

Process research and development of the fully synthetic broad spectrum tetracycline TP-2758, with a chiral pyrrolidine side chain at the C-8 position, is described. The process utilizes two key intermediates, 7 and 10, in a convergent approach that allows for manufacturing of sufficient quantities of API to supply preclinical and early clinical development. The pyrrolidine moiety was introduced into the left-hand piece (LHP) 10 with high enantioselectivity using Ellman's sulfinamide chemistry, and the absolute configuration was confirmed by X-ray crystal structure analysis.

Synthesis and Biological Evaluation of Kibdelone C and Its Simplified Derivatives

Poylcyclic tetrahydroxanthones comprise a large class of cytototoxic natural products. No mechanism of action has been described for any member of the family. We report the synthesis of kibdelone C and several simplified analogs. Both enantiomers of kibdeleone C show low nanomolar cytotoxicity toward multiple human cancer cell lines. Moreover, several simplified derivatives with improved chemical stability display higher activity than the natural product itself. In vitro studies rule out interaction with DNA or inhibition of topoisomerase, both of which are common modes of action for polycyclic aromatic compounds. However, celluar studies reveal that kibdelone C and its simplified derivatives disrupt the actin cytoseketon without directly binding actin or affecting its polymerization in vitro.

Enantioselective total synthesis of ( - )-kibdelone C

The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C - H arylation to complete the hexacyclic skeleton.

Storable arylpalladium(II) reagents for alkene labeling in aqueous media

We show that arylpalladium(II) reagents linked to biotin and indocyanine dye residues can be prepared by decarboxylative palladation of appropriately substituted electron-rich benzoic acid derivatives. When prepared under the conditions described, these organometallic intermediates are tolerant of air and water, can be stored for several months in solution in dimethyl sulfoxide, and permit biotin- and indocyanine dye-labeling of functionally complex olefinic substrates in water by Heck-type coupling reactions.

Nanometer-scale water-soluble macrocycles from nanometer-sized amino acids

"Chemical Equation Presented" This paper introduces the unnatural amino acids m-Abc2k and o-Abc2k as nanometer-sized building blocks for the creation of water-soluble macrocycles with well-defined shapes. m-Abc2k and o-Abc

Nanometer-sized amino acids for the synthesis of nanometer-scale water-soluble molecular rods of precise length

This paper introduces the unnatural amino acid Abc2K as a nanometer-length building block for the creation of water-soluble molecular rods of exceptional size. Abc2K is a water-soluble variant of the unnatural amino acid 4′-amino-[1,