28955-70-6

Basic information

• Product Name: 2(3H)-Benzoxazolone, 4-hydroxy-
• Synonyms: 2(3H)-Benzoxazolone, 4-hydroxy-;furo[3,4-b]pyridine-5,7-diol
• CAS NO: 28955-70-6
• Molecular Formula: C₇H₅NO₃
• Molecular Weight: 151.12
• Mol File: 28955-70-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2(3H)-Benzoxazolone, 4-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Benzoxazolone, 4-hydroxy-(28955-70-6)
• EPA Substance Registry System: 2(3H)-Benzoxazolone, 4-hydroxy-(28955-70-6)

Safety Data

• Hazardous Substances Data: 28955-70-6(Hazardous Substances Data)

Usage

Structure

A derivative of benzoxazolone with a hydroxyl group attached to the fourth carbon atom of the benzene ring.

Usage

Commonly used as a fluorescent probe in biological and chemical research.

Photophysical properties

Unique properties that make it suitable for use as a fluorescent probe.

Potential applications

Detection of reactive oxygen species and as a sensor for metal ions.

Therapeutic implications

Investigation for antioxidant and anti-inflammatory properties, with potential applications in treating neurodegenerative diseases and oxidative stress-related disorders.

Upstream product

• 3163-15-3 2-aminoresorcinol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 601-89-8 2-nitroresorcinol 
• 57-13-6 urea 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 634-60-6 2-aminoresorcinol hydrochloride 

Downstream Products

• 1082928-62-8 4-[2-(tert-butoxycarbonylamino)3-phenyl]propionyloxy-2(3H)-benzoxazolone 

Relevant articles and documents

4-Sulfonyloxy/alkoxy benzoxazolone derivatives with high anti-inflammatory activities: Synthesis, biological evaluation, and mechanims of action via p38/ERK-NF-κB/iNOS pathway

In an effort to discover new agents with high anti-inflammatory activity, 22 new 4-sulfonyloxy/alkoxy benzoxazolone derivatives were synthesized, characterized, and evaluated for their anti-inflammatory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production and TNF-α expression in RAW 264.7 cells in vitro. Most of these compounds displayed greater inhibitory ability against NO production than the lead compound 4-o-methyl-benzenesulfonyl benzoxazolone, and the most active compound 2h exhibited the strongest inhibitory activity against NO, IL-1β, and IL-6 production with IC50 values 17.67, 20.07, and 8.61?μΜ, respectively. The effects of 2h were comparable or stronger than those of the positive control celecoxib. Compound 2h also displayed higher activity in vivo than celecoxib in a mouse model of xylene-induced ear edema, based on their inhibitory rates of 42.69% and 30.87%, respectively. Further molecular analysis revealed that compound 2h significantly reduced the iNOS levels in cell supernatant and suppressed the protein expression of iNOS, p-p38, p-ERK, and nuclear NF-κB. The results indicated that the anti-inflammatory effect of 2h might be realized through the regulation of ERK- and p38-mediated mitogen-activated protein kinase (MAPK)-NF-κB/iNOS signaling, thereby reducing the excessive release of NO, IL-1β, and IL-6. Our findings demonstrated that compound 2h, a new benzoxazolone derivative, could inhibit activation of the MAPK-NF-κB/iNOS pathway, supporting its potential as a novel anti-inflammatory agent.

Design and synthesis of new disubstituted benzoxazolone derivatives that act as iNOS inhibitors with potent anti-inflammatory activity against LPS-induced acute lung injury (ALI)

Acute lung injury (ALI) is a pulmonary disease that acts as a severe acute inflammatory response with no specific drugs. iNOS, a catalyst of the excessive production of NO, has been demonstrated to participate in the inflammatory process, and targeting iNOS may be a promising therapeutic pathway to alleviate ALI. In our research, eighteen new disubstituted benzoxazolone derivatives were synthesized, characterized, and evaluated for activity against NO production in an LPS-induced RAW264.7 cell. The results showed that these compounds could obviously inhibit the over-generation of NO and disubstitution at the 4, N-position of the benzoxazolone ring, presenting better potency than substitution only at the 4-position. Among the analogues generated, compounds 2c, 2d, and 3d showed NO inhibitory activity with IC50 values of 16.43, 14.72, and 13.44 μM and iNOS inhibitory activity with IC50 values of 4.605, 3.342, and 9.733 μM, respectively. Meanwhile, compounds 2c, 2d, and 3d could also inhibit the release of IL-6, IL-1β in vitro and suppress xylene-induced ear edema in vivo to realize anti-inflammatory activity. Furthermore, compound 2d could significantly protect the LPS-induced ALI, presenting as decreased inflammatory cytokines and obvious pathological changes. Immunohistochemistry and molecular modeling demonstrated that compound 2d significantly inhibited the expression of iNOS in vivo and interacted with iNOS through two hydrogen bindings with the MET368 and ILE195 residues of the iNOS protein. These results demonstrated that compound 2d could be a promising lead structure for iNOS inhibitors, with anti-inflammatory activity to treat LPS-induced acute lung injury.

Na2O-Al2O3-P2O5 glass-ceramic system: Efficient catalyst for the aqueous Media Preparation of Pyrano[2,3-e]benzoxazole Derivatives

A highly efficient and environmentally benign protocol for the synthesis of 8-amino-6-aryl-1,2-dihydro-2-oxo-6H-pyrano[2,3-e]benzoxazole-7-carbonitrile derivatives by one-pot threecomponent coupling reacting of aromatic aldehydes, malononitrile and 4-hydr