871367-14-5

Usage

Molecular Weight

214.04 g/mol

Structure

A bicyclic compound consisting of a benzene ring fused to a five-membered oxazole ring, with a bromine atom at the 7th position.

+ Appearance

White or pale yellow crystalline solid

+ Melting Point

142-146°C

+ Solubility

Slightly soluble in water, soluble in common organic solvents such as ethanol, methanol, and acetone.

+ Reactivity

The presence of the bromine atom at the 7th position makes the compound more reactive towards nucleophilic substitution reactions.

+ Functional Groups

The compound contains a lactone ring, an oxazole ring, and a bromine atom.

Biological Activities

The benzoxazolone family of compounds is known for its diverse biological activities, including antitumor, anti-inflammatory, and antimicrobial properties.

+ Pharmaceutical Industry

The compound has potential as a drug candidate for the treatment of various diseases due to its ability to modulate biological pathways.

+ Agrochemical Industry

The compound may be used as a pesticide or herbicide due to its ability to disrupt the growth and development of plants.

+ Materials Science

The compound's structural versatility may make it useful in the development of new materials with unique properties.

Research Interest

2(3H)-benzoxazolone, 7-bromohas shown promise in drug discovery and development, making it an intriguing target for further research and investigation.

InChI:InChI=1/C7H4BrNO2/c8-4-2-1-3-5-6(4)11-7(10)9-5/h1-3H,(H,9,10)

Upstream product

• 28165-50-6 2-amino-6-bromophenol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 13073-25-1 2-bromo-6-nitro-phenol 
• 3883-95-2 3-bromosalicylic acid 
• 1319081-99-6 3-bromo-2-hydroxybenzoyl azide 
• 1261615-73-9 3-bromo-2-hydroxybenzoyl chloride 
• 81282-60-2 7-aminobenzo[d]oxazol-2(3H)-one 

Relevant academic research and scientific papers

Structure, preparation method and application of a series of benzoxazolone derivatives

The invention discloses a structure, a preparation method and an application of a series of benzoxazolone derivatives, and particularly provides a benzoxazolone compound structure shown as a compoundI, a synthesis method, and an application of pharmaceutically acceptable salt or a mixture of the pharmaceutically acceptable salt in preparation of drugs for preventing and/or treating diabetic complications. The compounds are used as aldose reductase inhibitors and antioxidants, and also have the effect of reducing blood sugar. The compound can reduce blood sugar, inhibit the activity of aldosereductase, scavenge free radicals, inhibit the generation of lipid peroxide and improve the content of glutathione and the activity of superoxide dismutase, so that the urine protein level is reduced,and the effect of preventing and/or treating diabetic complications, especially diabetic nephropathy, is achieved. The invention also provides a pharmaceutical composition containing the compound andhaving the effect of preventing and/or treating diabetic complications; wherein X is a single bond, or is -CH=CH- and the R1 is hydrogen, hydroxyl, methoxyl or trifluoromethyl, and R2 is hydrogen, methoxyl or hydroxyl.

Multifunctional agents based on benzoxazolone as promising therapeutic drugs for diabetic nephropathy

Diabetic nephropathy (DN) is resulted from activations of polyol pathway and oxidative stress by abnormal metabolism of glucose, and no specific medication is available. We designed a novel class of benzoxazolone derivatives, and a number of individuals were found to have significant antioxidant activity and inhibition of aldose reductase of the key enzyme in the polyol pathway. The outstanding compound (E)-2-(7-(4-hydroxy-3-methoxystyryl)-2-oxobenzo[d]oxazol-3(2H)-yl)acetic acid was identified to reduce urinary proteins in diabetic mice suggesting an alleviation in the diabetic nephropathy, and this was confirmed by kidney hematoxylin-eosin staining. Further investigations showed blood glucose normalization, declined in the polyol pathway and lipid peroxides, and raised glutathione and superoxide dismutase activity. Thus, we suggest a therapeutic function of the compound for DN which could be attributed to the combination of hypoglycemic, aldose reductase inhibition and antioxidant.

CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF

Small molecule calpain modulator compounds, including their pharmaceutically acceptable salts, can be included in pharmaceutical compositions. The compounds can be useful in inhibiting calpain, or competitive binding with calpastatin, by contacting them with CAPN1, CAPN2, and/or CAPN9 enzymes residing inside a subject. The compounds and composition can also be administered to a subject in order to treat a fibrotic disease or a secondary disease state or condition of a fibrotic disease.

Iron-Catalyzed Arene C-H Amidation Using Functionalized Hydroxyl Amines at Room Temperature

Herein, we report Fe(III)(TPP)Cl as an effective catalyst for promoting arene C-H amidation through intramolecular cyclization of N-tosyloxyarylcarbamate substrates. The reaction proceeds via nitrene (outer sphere pathway) C(sp2)-H i

Novel benzoxazolone compound

PROBLEM TO BE SOLVED: To provide a therapeutic agent for diseases such as neuropathic pain, nociceptive pain, inflammatory pain, small diameter fiber neuropathy, erythromelalgia, paroxysmal extreme pain disorder, dysuria or multiple sclerosis. SOLUTION: There is provided a benzoxazolone compound represented by the formula (1) or a pharmaceutically acceptable salt. (1), where R1 and R2 are each independently H or C1-6 alkyl, where the alkyl may be substituted by hydroxy, C1-4 alkylsulfonyl, aminocarbonyl or 4 to 7-membered heterocycloalkyl, or the like, L is C1-6 alkylene, R3 is C1-6 alkyl, C3-7 cycloalkyl, where the cycloalkyl may be substituted by halogen or hydroxy or the like, C6-10 aryl, where the aryl may be substituted by halogen, C1-4 alkyl or C1-4 haloalkyl or the like, R4 is H, halogen or C1-4 alkyl. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Synthesizing method for 3'-amino-2'-hydroxy biphenyl-3-carboxylic acid

The invention discloses a synthesizing method for 3'-amino-2'-hydroxy biphenyl-3-carboxylic acid.2-bromine-6-nitrophenol serves as a staring material, 2-bromine-6-aminophenol is obtained through a reduction reaction, ring formation and Suzuki coupling are carried out, a hydrolysis reaction is carried out, and 3'-amino-2'-hydroxy biphenyl-3-carboxylic acid is obtained. According to the method, raw materials are easy to obtain, the path is short, and the method is novel, low in cost, high in yield and environmentally friendly. Tests show that the obtained product is reliable in quality, stable in performance and capable of being further used for preparing a thrombopoietin receptor stimulant, namely, eltrombopag olamine.

Benzoxazolone Carboxamides as Potent Acid Ceramidase Inhibitors: Synthesis and Structure-Activity Relationship (SAR) Studies

Ceramides are lipid-derived intracellular messengers involved in the control of senescence, inflammation, and apoptosis. The cysteine amidase, acid ceramidase (AC), hydrolyzes these substances into sphingosine and fatty acid and, by doing so, regulates their signaling activity. AC inhibitors may be useful in the treatment of pathological conditions, such as cancer, in which ceramide levels are abnormally reduced. Here, we present a systematic SAR investigation of the benzoxazolone carboxamides, a recently described class of AC inhibitors that display high potency and systemic activity in mice. We examined a diverse series of substitutions on both benzoxazolone ring and carboxamide side chain. Several modifications enhanced potency and stability, and one key compound with a balanced activity-stability profile (14) was found to inhibit AC activity in mouse lungs and cerebral cortex after systemic administration. The results expand our arsenal of AC inhibitors, thereby facilitating the use of these compounds as pharmacological tools and their potential development as drug leads.

SUBSTITUTED BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to substituted benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides substituted benzoxazolone derivatives for use in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

ANTI-FIBROTIC PYRIDINONES

This application relates to polycyclic compounds with a pyridinone or pyridinone derivative core including, substituted pyridinones, 5,6- and 6,6- bicyclic heterocycles and substituted pyridine-thiones. This application also discloses methods of preparing these polycyclic compounds, pharmaceutical compositions and medicaments comprising said compounds and methods to treat, prevent or diagnose diseases, disorders or conditions associated with fibrosis.

BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides benzoxazolone derivatives for use as a medicament in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.