28955-70-6

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

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

Downstream Products

• 1082928-62-8 4-[2-(tert-butoxycarbonylamino)3-phenyl]propionyloxy-2(3H)-benzoxazolone 
• 1082928-46-8 C₁₄H₉NO₄ 
• 1082928-56-0 C₁₄H₈ClNO₄ 
• 1429193-58-7 C₁₄H₈ClNO₄ 
• 1429193-59-8 C₁₄H₈ClNO₄ 
• 1429193-60-1 C₁₄H₈N₂O₆ 
• 1429193-61-2 C₁₄H₈N₂O₆ 
• 1429193-62-3 C₁₄H₈N₂O₆ 
• 1429193-63-4 C₁₅H₁₁NO₄ 
• 1429193-64-5 C₁₅H₁₁NO₄ 
• 1429193-65-6 C₁₅H₁₁NO₄ 
• 1082928-48-0 C₁₃H₉NO₅S 
• 1429193-66-7 C₁₃H₈ClNO₅S 
• 1429193-67-8 C₁₃H₈ClNO₅S 

Relevant academic research and scientific papers

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.

4-hydroxybenzo[d]oxazol-2(3H)-one ameliorates LPS/D-GalN-induced acute liver injury by inhibiting TLR4/NF-κB and MAPK signaling pathways in mice

The purpose of this study was to synthesize 4-hydroxybenzo[d]oxazol-2(3H)-one (HBO) and to investigate its protective effects on lipopolysaccharide (LPS)/D-galactosamine (D-GalN)-induced acute liver injury. HBO (C7H5O3N) was synthesized based on 2-nitro-resorcinol and identified by physicochemical analysis. In the animal experiment, mice were pretreated with HBO (50, 100, 200 mg/kg) for 10 days. At the end of pretreatment, the animals were injected with LPS (10 μg/kg)/D-GalN (700 mg/kg). The results showed that HBO significantly alleviated liver injury induced by LPS/D-GalN in mice. It remarkably decreased inflammatory response by reducing the levels of tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β). Moreover, HBO notably attenuated hepatocyte apoptosis by inhibiting the release of Cytochrome C (Cyt C) from mitochondria into the cytoplasm and regulating the expression of B-cell lymphoma-2 (Bcl-2) family. Furthermore, the result showed that HBO inhibited the expressions of nuclear factor kappa-B p50 (NF-κBp50), toll-like receptor 4 (TLR4), and myeloid differentiation factor 88 (MyD88), as well as the phosphorylation of inhibitor of nuclear factor kappa-B (IκB), inhibitor of nuclear factor kappa-B kinase-α/β (IKK-α/β), nuclear factor kappa-B p65 (NF-κBp65), suggesting that HBO had a certain influence on the TLR4/NF-κB pathway. In addition, the mitogen-activated protein kinase (MAPK) signaling pathway was also affected by HBO, as evidenced by the decrease in the phosphorylation levels of extracellular regulated protein kinase 1/2 (ERK1/2), c-Jun N-terminal kinase (JNK) and p38 mitogen-activated protein kinase (p38). In conclusion, our study suggested that HBO could protect against LPS/D-GalN-induced liver injury, moreover, treatment with HBO appeared to be capable of further regulating the TLR4/NF-κB and MAPK signaling pathways.

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.

Synthesis, Anti-Inflammatory, and Analgesic Activities of Derivatives of 4-Hydroxy-2-benzoxazolone

Benzoxazolones are widely distributed in plants and are of increasing interest for a variety of pharmacological properties, such as detoxification, antibacterial, anti-inflammatory, and analgesic activities and tranquilizers (Michaelidou and Hadjipavlou-L

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

Synthesis and biological activity of 4-substituted benzoxazolone derivatives as a new class of sEH inhibitors with high anti-inflammatory activity in vivo

A series of novel 4-substituted benzoxazolone derivatives was synthesized, characterized and evaluated as human soluble epoxide hydrolase (sEH) inhibitors and anti-inflammatory agents. Some compounds showed moderate sEH inhibitory activities in vitro, and two novel compounds, 3g and 4j, exhibited the highest activities with IC50 values of 1.72 and 1.07 μM, respectively. Structure-activity relationships (SARs) revealed that introduction of a lipophilic amino acid resulted in an obvious increase in the sEH inhibitory activity, especially for derivatives containing a phenyl (3d, IC50 = 2.67 μM), pyrrolidine (3g, IC50 = 1.72 μM), or sulfhydryl group (3e, IC50 = 3.02 μM). Several compounds (3a-3g) were tested in vivo using a xylene-induced ear edema mouse model. Three compounds (3d, 3f, and 3g) showed strong anti-inflammatory activities in vivo which were higher than that of Chlorzoxazone, a reference drug widely used in the clinic. Our investigation provided a novel type of sEH inhibitor and anti-inflammatory agent that may lead to the discovery of a potential candidate for clinical use.

Synthesis and activities of new 4-hydroxy benzoxazolone derivatives

A series of new 4-substituted benzoxazolone derivatives were synthesized according to a convenient method, their anti-inflammatory and analgesic activities in vivo were evaluated. All of them were new compounds, the structures of all the synthesized compounds were confirmed by 1H NMR, 13C NMR, ESI-MS and HR-MS. Most of the compounds exhibited anti-inflammatory activity.

Sulfonamide peri-substituted bicyclics for occlusive artery disease

Acyl sulfonamide, peri-substituted, fused bicyclic ring compounds useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed. The compounds are of the general formula A representative example is:

CARBOXYLIC ACID PERI - SUBSTITUTED BICYCLICS FOR OCCLUSIVE ARTERY DISEASE

Peri-substituted, fused bicyclic ring carboxylic acids useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed.