5840-66-4

Usage

Molecular weight

244.24 g/mol

Appearance

White solid with a slight odor

Solubility

Insoluble in water

Uses

a. Building block in the synthesis of pharmaceuticals
b. Building block in the synthesis of agrochemicals
c. Building block in the synthesis of specialty chemicals
d. Coupling agent for the preparation of amide bond and ester bond linkages in organic synthesis
e. Potential applications in the production of fragrances
f. Potential applications in the production of flavoring agents
g. Potential applications in the production of polymer additives

Safety precautions

May cause skin and eye irritation upon contact; handle and store with caution

Upstream product

• 610-35-5 4-hydroxyphthalic acid 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 5840-67-5 4-Benzyloxy-phthalsaeure-dimethylester 

Downstream Products

• 1332697-26-3 C₂₉H₂₉NO₄ 
• 447424-15-9 6-(benzyloxy)-3-(hydroxymethyl)-2-(2-methylpropyl)-4-phenylisoquinolin-1(2H)-one 
• 447424-16-0 6-(benzyloxy)-3-(chloromethyl)-2-(2-methylpropyl)-4-phenylisoquinolin-1(2H)-one 
• 447424-17-1 2-{[6-(benzyloxy)-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]methyl}-1H-isoindole-1,3(2H)-dione 
• 447424-27-3 ethyl 6-(benzyloxy)-4-hydroxy-2-(2-methylpropyl)-1-oxo-1,2-dihydroisoquinoline-3-carboxylate 
• 1332697-25-2 ethyl 6-(benzyloxy)-2-(2-methylpropyl)-1-oxo-4-{[(trifluoromethyl)sulfonyl]oxy}-1,2-dihydroisoquinoline-3-carboxylate 
• 447424-14-8 6-(benzyloxy)-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid 
• 447424-18-2 tert-butyl {[6-(benzyloxy)-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]methyl}carbamate 
• 447424-19-3 tert-butyl {[6-hydroxy-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]methyl}carbamate 
• 447424-20-6 tert-butyl {[6-(2-amino-2-oxoethoxy)-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl]methyl}carbamate 
• 447416-94-6 2-{[3-(aminomethyl)-2-(2-methylpropyl)-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl]oxy}acetamide hydrochloride 
• 1332697-02-5 3-(aminomethyl)-6-hydroxy-2-(2-methylpropyl)-4-phenylisoquinolin-1(2H)-one hydrochloride 
• 94464-27-4 2-(2,6-dioxo-3-piperidinyl)-5-benzyloxy-1H-isoindole-1,3(2H)-dione 
• 928776-72-1 5-benzyloxy-2-(5-tert-butyldimethylsilyloxy-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

Small Molecule Inhibitors of the BfrB-Bfd Interaction Decrease Pseudomonas aeruginosa Fitness and Potentiate Fluoroquinolone Activity

The iron storage protein bacterioferritin (BfrB) is central to bacterial iron homeostasis. The mobilization of iron from BfrB, which requires binding by a cognate ferredoxin (Bfd), is essential to the regulation of cytosolic iron levels in P. aeruginosa. This paper describes the structure-guided development of small molecule inhibitors of the BfrB-Bfd protein-protein interaction. The process was initiated by screening a fragment library and followed by obtaining the structure of a fragment hit bound to BfrB. The structural insights were used to develop a series of 4-(benzylamino)- A nd 4-((3-phenylpropyl)amino)-isoindoline-1,3-dione analogs that selectively bind BfrB at the Bfd binding site. Challenging P. aeruginosa cells with the 4-substituted isoindoline analogs revealed a dose-dependent growth phenotype. Further investigation determined that the analogs elicit a pyoverdin hyperproduction phenotype that is consistent with blockade of the BfrB-Bfd interaction and ensuing irreversible accumulation of iron in BfrB, with concomitant depletion of iron in the cytosol. The irreversible accumulation of iron in BfrB prompted by the 4-substituted isoindoline analogs was confirmed by visualization of BfrB-iron in P. aeruginosa cell lysates separated on native PAGE gels and stained for iron with Ferene S. Challenging P. aeruginosa cultures with a combination of commercial fluoroquinolone and our isoindoline analogs results in significantly lower cell survival relative to treatment with either antibiotic or analog alone. Collectively, these findings furnish proof of concept for the usefulness of small molecule probes designed to dysregulate bacterial iron homeostasis by targeting a protein-protein interaction pivotal for iron storage in the bacterial cell.

Identification of 3-aminomethyl-1,2-dihydro-4-phenyl-1-isoquinolones: A new class of potent, selective, and orally active non-peptide dipeptidyl peptidase IV inhibitors that form a unique interaction with Lys554

The design, synthesis, and structure-activity relationships of a new class of potent and orally active non-peptide dipeptidyl peptidase IV (DPP-4) inhibitors, 3-aminomethyl-1,2-dihydro-4-phenyl-1-isoquinolones, are described. We hypothesized that the 4-ph

Mono- and dihydroxylated metabolites of thalidomide: Synthesis and TNF-α production-inhibitory activity

Mono- and dihydroxylated metabolites of thalidomide were efficiently prepared and characterized, and their inhibitory activity on tumor necrosis factor (TNF)-α production in the human monocytic leukemia cell line THP-1 was evaluated. 5,N-Dihydroxythalidomide was a much more potent TNF-α production inhibitor than thalidomide.