399-00-8

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-4-FLUORO-2-HYDROXY-BENZALDEHYDE is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique structure allows for the creation of complex organic molecules that can be used in the development of new drugs and medications.
Used in Chemical Manufacturing Industry:
5-BROMO-4-FLUORO-2-HYDROXY-BENZALDEHYDE is used as a building block in the synthesis of other complex organic molecules. Its intermediate reactivity makes it a valuable component in the production of various chemicals and materials.
Used in Organic Synthesis:
5-BROMO-4-FLUORO-2-HYDROXY-BENZALDEHYDE is used as a key component in organic synthesis processes. Its presence in the molecular structure can lead to the formation of new compounds with potential applications in various fields, such as materials science, agrochemicals, and more.

Upstream product

• 67-66-3 chloroform 
• 372-20-3 3-fluorophenol 
• 7726-95-6 bromine 
• 77771-02-9 3-bromo-4-fluorobenzaldehyde 
• 348-28-7 4-fluoro-2-hydroxybenzaldehyde 

Downstream Products

• 361-44-4 5-bromo-4-fluoro-2-hydroxy-3-nitro-benzaldehyde 

Relevant academic research and scientific papers

Structure-Based Design of Potent and Orally Active Isoindolinone Inhibitors of MDM2-p53 Protein-Protein Interaction

Inhibition of murine double minute 2 (MDM2)-p53 protein-protein interaction with small molecules has been shown to reactivate p53 and inhibit tumor growth. Here, we describe rational, structure-guided, design of novel isoindolinone-based MDM2 inhibitors. MDM2 X-ray crystallography, quantum mechanics ligand-based design, and metabolite identification all contributed toward the discovery of potent in vitro and in vivo inhibitors of the MDM2-p53 interaction with representative compounds inducing cytostasis in an SJSA-1 osteosarcoma xenograft model following once-daily oral administration.

Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient Directing Group

The direct Pd-catalyzed ortho C-H hydroxylation of benzaldehydes was achieved using 4-chloroanthranilic acid as the transient directing group, 1-fluoro-2,4,6-trimethylpyridnium triflate as the bystanding oxidant, and p-toluenesulfonic acid as the putative oxygen nucleophile. The unusual C-H chlorination and polyfluoroalkoxylation reactions signaled the importance of external nucleophiles to the outcome of Pd(IV) reductive eliminations.

Structure-based design of tricyclic NF-κB inducing kinase (NIK) inhibitors that have high selectivity over phosphoinositide-3-kinase (PI3K)

We report here structure-guided optimization of a novel series of NF-κB inducing kinase (NIK) inhibitors. Starting from a modestly potent, low molecular weight lead, activity was improved by designing a type 11/2 binding mode that accessed a back pocket past the methionine-471 gatekeeper. Divergent binding modes in NIK and PI3K were exploited to dampen PI3K inhibition while maintaining NIK inhibition within these series. Potent compounds were discovered that selectively inhibit the nuclear translocation of NF-κB2 (p52/REL-B) but not canonical NF-κB1 (REL-A/p50).

Discovery of 7-tetrahydropyran-2-yl chromans: β-site amyloid precursor protein cleaving enzyme 1 (BACE1) inhibitors that reduce amyloid β-protein (Aβ) in the central nervous system

In an attempt to increase selectivity vs Cathepsin D (CatD) in our BACE1 program, a series of 1,3,4,4a,10,10a-hexahydropyrano[4,3-b]chromene analogues was developed. Three different Asp-binding moieties were examined: spirocyclic acyl guanidines, aminooxazolines, and aminothiazolines in order to modulate potency, selectivity, efflux, and permeability. Using structure-based design, substitutions to improve binding to both the S3 and S2′ sites of BACE1 were explored. An acyl guanidine moiety provided the most potent analogues. These compounds demonstrated 10-420 fold selectivity for BACE1 vs CatD, and were highly potent in a cell assay measuring Aβ1-40 production (5-99 nM). They also suffered from high efflux. Despite this undesirable property, two of the acyl guanidines achieved free brain concentrations (C free,brain) in a guinea pig PD model sufficient to cover their cell IC50s. Moreover, a significant reduction of Aβ1-40 in guinea pig, rat, and cyno CSF (58%, 53%, and 63%, respectively) was observed for compound 62.

CONDENSED TRICLYCLIC COMPOUNDS AS INHIBITORS OF HIV REPLICATION

Compounds of formula (I) and pharmaceutical compositions thereof: wherein A1 A2 and A3 are each independently selected from the group consisting of N and CR3, wherein R1 is an optionally substituted heterocyclyl or an optionally substituted -(C1-6)alkyl-heterocyclyl, R2 is an optionally substituted aryl or an optionally subsisted heteroaryl, R4 is an optionally substituted aryl, an optionally substituted heterocyclyl or an optionally substituted heteroaryl, useful as an inbitor of HIV replication.

COMPOUNDS FOR TREATING NEURODEGENERATIVE DISEASES

The invention provides novel tricyclic compounds of Formula I' that inhibit β-secretase cleavage of APP and are useful as therapeutic agents for treating neurodegenerative diseases.

Synthesis and structure-activity relationships of a novel series of 2,3,5,6,7,9-hexahydrothieno[3,2-b]quinoline-8(4H)-one 1,1-dioxide K ATP channel openers: Discovery of (-)-(9S)-9-(3-bromo-4-fluorophenyl)-2,3,5,6,7,9-hexahydrothieno[3,2-b] quinolin-8(4H)-one 1,1-dioxide (A-278637), a potent KATP opener that selectively inhibits spontaneous bladder contractions

Structure-activity relationships were investigated on a novel series of sulfonyldihydropyridine-containing KATP openers. Ring sizes, absolute stereochemistry, and aromatic substitution were evaluated for K ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a select group of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation. In an anesthetized pig model of myogenic bladder overactivity, compound 14 and (-)-cromakalim 1 were found to inhibit spontaneous bladder contractions in vivo at plasma concentrations lower than those that affected hemodynamic parameters. Compound 14 showed approximately 5-fold greater selectivity than 1 in vivo and supports the concept that bladder-selective KATP channel openers may have utility in the treatment of overactive bladder.

Pyrano, piperidino, and thiopyrano compounds and methods of use

The present invention provides novel compounds of formula I which may be useful in hyperpolarizing cell membranes, opening potassium channels, relaxing smooth muscle cells, and inhibiting bladder contractions.

Potassium channel openers

Compounds having the formula I: are useful in treating diseases prevented by or ameliorated with potassium channel openers. Also disclosed are potassium channel opening compositions and a method of opening potassium channels in a mammal.