24050-49-5

Basic information

• Product Name: 3-BROMO-1,8-NAPHTHALIC ANHYDRIDE
• Synonyms: 3-BROMO-1,8-NAPHTHALIC ANHYDRIDE;5-BroMobenzo[de]isochroMene-1,3-dione;1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 5-broMo-;5-Bromo-1H,3H-benzo[de]isochromene-1,3-dione
• CAS NO: 24050-49-5
• Molecular Formula: C₁₂H₅BrO₃
• Molecular Weight: 277.07
• EINECS: -0
• Mol File: 24050-49-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 244-246°C
• Boiling Point: 468.9 °C at 760 mmHg
• Flash Point: 237.4 °C
• Appearance: /
• Density: 1.812±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.78E-09mmHg at 25°C
• Refractive Index: 1.733
• Sensitive: Moisture Sensitive
• BRN: 180001
• CAS DataBase Reference: 3-BROMO-1,8-NAPHTHALIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-1,8-NAPHTHALIC ANHYDRIDE(24050-49-5)
• EPA Substance Registry System: 3-BROMO-1,8-NAPHTHALIC ANHYDRIDE(24050-49-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 24050-49-5(Hazardous Substances Data)

Usage

Description

3-Bromo-1,8-naphthalic anhydride is an organic compound with the molecular formula C11H5BrO3. It is characterized by the presence of a bromine atom at the 3-position and an anhydride group at the 1,8-positions of the naphthalene ring. 3-BROMO-1,8-NAPHTHALIC ANHYDRIDE is known for its potential applications in the pharmaceutical and chemical industries due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
3-Bromo-1,8-naphthalic anhydride is used as a key intermediate in the synthesis of novel NK1/NK2 antagonists. These antagonists are important for the development of drugs targeting neurokinin receptors, which are involved in various physiological processes and diseases, including pain, inflammation, and psychiatric disorders.
Additionally, 3-Bromo-1,8-naphthalic anhydride is used as a starting material in the synthesis of antitumor active alanediamines. These compounds have shown potential in the development of anticancer drugs, as they can inhibit the growth and proliferation of cancer cells by targeting specific molecular pathways.

InChI:InChI=1/C12H5BrO3/c13-7-4-6-2-1-3-8-10(6)9(5-7)12(15)16-11(8)14/h1-5H

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 

Downstream Products

• 16726-66-2 3-bromo-1-naphthoic acid 
• 51934-38-4 6-bromo-1-naphthoic acid 
• 181779-85-1 3-phenylnaphthalic anhydride 
• 93353-66-3 methyl 6-bromonaphthalene-1-carboxylate 
• 16650-63-8 3-bromo-naphthalene-1-carboxylic acid methyl ester 
• 1419321-08-6 3-bromo-N-(4-aminobenzyl)-1,8-naphthalimide 

Relevant articles and documents

Direct amidation to access 3-amido-1,8-naphthalimides including fluorescent scriptaid analogues as hdac inhibitors

Methodology to access fluorescent 3-amido-1,8-naphthalimides using direct Buchwald– Hartwig amidation is described. The protocol was successfully used to couple a number of substrates (including an alkylamide, an arylamide, a lactam and a carbamate) to 3-bromo-1,8-naphthalimide in good yield. To further exemplify the approach, a set of scriptaid analogues with amide substituents at the 3-position were prepared. The new compounds were more potent than scriptaid at a number of histone deacetylase (HDAC) isoforms including HDAC6. Activity was further confirmed in a whole cell tubulin deacetylation assay where the inhibitors were more active than the established HDAC6 selective inhibitor Tubastatin. The optical properties of these new, highly active, compounds make them amenable to cellular imaging studies and theranostic applications.

Discovery of novel small molecule induced selective degradation of the bromodomain and extra-terminal (BET) bromodomain protein BRD4 and BRD2 with cellular potencies

The BET proteins BRD2, BRD3, and BRD4 play important roles in transcriptional regulation and can be degraded by proteolysis-targeting chimeras (PROTACs) for BET proteins. However, the lack of intra-BET proteins selectivity limits the scope of current degraders as probes for target validation and could lead to unwanted side effects or toxicity in a therapeutic setting. We describe herein the design, synthesis, and evaluation of PROTAC BET degraders, based on the BET inhibitor with selectivity for the first Bromodomain benzo[cd]indole-2-one, alkylamide linker and cereblon ligand thalidomide. Compound 15 potently and rapidly induces reversible, long-lasting, and unexpectedly selective removal of BRD4 and BRD2 over BRD3, which not only effectively inhibits cell growth in human acute leukemia cell lines, but also very effective in inhibiting solid tumors with low cytotoxic effect in the cell profiles of NCI 60 cell lines. Remarkable dependency on linker length was observed for BRD4-degrading and c-Myc-driven antiproliferative activities in acute myeloid leukemia cell line MV4-11. The small-molecular 15 represents a novel, potent, and selective class of BRD4 and BRD2 degraders for the development of therapeutics to treat cancers.

Benzoindole bifunctional molecular derivatives as well as preparation method and application thereof

The invention belongs to the field of medical chemistry, and particularly relates to benzoindole bifunctional molecule derivatives as well as a preparation method and application thereof. The benzoindole bifunctional molecule of the derivative, or tautomer, mesomer, raceme, enantiomer, diastereomer, hydrate or pharmaceutically acceptable salt has a structure as shown in a general formula (I). Thederivative is a protein degradation targeting chimeric body (PROTACs) technology, and can induce the degradation of BET protein. The invention also discloses application of the bifunctional molecularcompound in medicines for preventing and/or treating BET protein related diseases.

Discovery of Benzo[ cd]indol-2(1 H)-ones and Pyrrolo[4,3,2- de]quinolin-2(1 H)-ones as Bromodomain and Extra-Terminal Domain (BET) Inhibitors with Selectivity for the First Bromodomain with Potential High Efficiency against Acute Gouty Arthritis

The bromodomain and extra-terminal domain (BET) family of proteins are readers which specifically recognize histone-acetylated lysine residues. Each BET bromodomain protein contains two highly homologous domains: the first bromodomain (BD1) and the second bromodomain (BD2). Pan-BET bromodomain inhibition is a potential therapy for various cancers and immune-inflammatory diseases, but only few reported inhibitors show selectivity within the BET family. Herein, we identified a series of benzo[cd]indol-2(1H)-ones and pyrrolo[4,3,2-de]quinolin-2(1H)-ones with good selectivity for BET BD1. Through structure-based optimization, highly active and selective compounds are ultimately obtained. The representative compounds are the first reported inhibitors with selectivity more than 100-fold for BRD4(1) over BRD4(2). Among them, we further show that 68 (LT052) mediates BRD4/NF-κB/NLRP3 signaling inflammatory pathways with comparable protein expression and significantly improves symptoms of gout arthritis in a rat model. Therefore, selective pharmacological modulation of individual bromodomains could represent a strategy for the treatment of acute gouty arthritis.