65240-86-0

Usage

Uses

Used in Pharmaceutical Applications:
2-Benzamido-1,4-naphthoquinone is used as an inhibitor for histone deacetylase (HDAC6) due to its ability to modulate the activity of this enzyme, which is involved in numerous biological processes and diseases. By targeting HDAC6, 2-BENZOYLAMINO-1,4-NAPHTHOQUINONE may have potential therapeutic applications in treating various conditions.
Furthermore, 2-Benzamido-1,4-naphthoquinone is used as an activation blocker of nuclear factor-kB (NF-kB) for its potential role in regulating cellular responses to various stimuli. Inhibition of NF-kB activation may be beneficial in the development of treatments for conditions where NF-kB plays a significant role, such as inflammatory and autoimmune diseases.

Biological Activity

ppm-18 is a chemically synthesized naphthoquinone derivative and an anti-inflammatory agent that inhibits the expression of inducible no synthase (inos). nos catalyzes the oxidation of the amino acid l-arginine to form no. as an important cellular signaling molecule, no has been implicated in modulating vascular tone, airway tone, insulinsecretion, and peristalsis. it has also been shown that no is involved in angiogenesis and neural development and can function as a retrograde neurotransmitter

in vitro

pretreatment of rat alveolar macrophages with ppm-18 (0.1-10 μm) significantly inhibited nitrite production, inos mrna accumulation and inos protein expression. ppm-18 did not affect the enzymic activities of inos and other constitutive nos forms directly. ppm-18 (10 μm) inhibited the lps-induced increase in nuclear transcription factor κb (nf-κb) p65 and p50 in nucleus.. ppm-18 significantly decreased lps-induced the production of tumour necrosis factor α [1]. ppm-18 inhibited nf-κb activation with an ic50 of 5 μm [3].

in vivo

in rats, intravenously pretreatment with ppm-18 (15 mg/kg) maintained a significantly higher mean arterial pressure compared with lps-treated controls. ppm-18 protected mice against lps-induced lethal toxicity. in mice, ppm-18 (5 or 15 mg/kg) dose-dependently decreased the lethality. in the mouse model of sepsis, ppm-18 exhibited as a potent inhibitor of inos expression by blocking the binding of nf-κb to promoter and exerted a beneficial effect [1].

references

[1] yu m s, lin j f w u t l, kuo c s. inhibition of nitric oxide synthase expression by ppm-18, a novel anti-inflammatory agent, in vitro and in vivo[j]. biochemical journal, 1997, 328(2): 363-369.[2] beck k f, eberhardt w, frank s, et al. inducible no synthase: role in cellular signalling[j]. journal of experimental biology, 1999, 202(6): 645-653.[3] davis, m. e.,grumbach, i.m.,fukai, t., et al. shear stress regulates endothelial nitric-oxide synthase promoter activity through nuclear factor κb binding.the journal of biological chemisty 279(1), 163-168 (2004).

InChI:InChI=1/C17H11NO3/c19-15-10-14(16(20)13-9-5-4-8-12(13)15)18-17(21)11-6-2-1-3-7-11/h1-10H,(H,18,21)

Upstream product

• 2348-81-4 2-amino-1,4-naphthoquinone 
• 98-88-4 benzoyl chloride 
• 130-15-4 [1,4]naphthoquinone 
• 75539-34-3 2-amino-naphthalene-1,4-diol 
• 93783-14-3 C₁₇H₁₃NO₃ 
• 2446-51-7 N-methoxybenzamide 
• 495-18-1 Benzohydroxamic acid 

Downstream Products

• 1134320-07-2 N-(1,4-dioxo-3-phenyl-1,4-dihydronaphthalen-2-yl)benzamide 

Relevant academic research and scientific papers

Silver-Catalyzed Three-Component Difunctionalization of Alkenes via Radical Pathways: Access to CF3-Functionalized Alkyl-Substituted 1,4-Naphthoquinone Derivatives

A silver-catalyzed three-component difunctionalization of alkenes by using 2-amino- and 2-hydroxy-1,4-naphthoquinone derivatives as the radical-trapping reagents is reported. Various alkenes and 2-amino- or 2-hydroxy-1,4-naphthoquinones with diverse struc

The one-pot synthesis of amidonapthoquinones from aminonaphthoquinones

Described here is a one-pot method of synthesizing amidonaphthoquinones from the corresponding aminonaphthoquinones. The scope of amides that can be synthesized using this methodology is relatively broad and the yield of product is higher than the traditional methods of synthesizing these substrates. 2009 Elsevier Ltd. All rights reserved.

Metal-Free Direct Amidation of Naphthoquinones Using Hydroxamic Acids as an Amide Source: Application in the Synthesis of an HDAC6 Inhibitor

A novel synthetic approach to amidoquinones by the reaction of naphthoquinones with hydroxamic acids under basic conditions was developed. The reaction is mild and operationally simple, and it affords high yields of amidoquinones. With this new method, a novel, very strong HDAC6 inhibitor, which showed high toxicity to AML cells, was successfully synthesized.

COMPOSITIONS AND METHODS FOR TREATING NEUROLOGICAL DISEASES OR INJURY

Provided are compounds for the treatment of neurological diseases or injuries, including neurodegenerative diseases, stroke, trauma, epilepsy, acute and chronic kidney injuries, diabetes mellitus, and/or seizures. In some embodiments, derivatives of vitamin K are provided.

Structure-activity relationship study of vitamin K derivatives yields highly potent neuroprotective agents

Historically known for its role in blood coagulation and bone formation, vitamin K (VK) has begun to emerge as an important nutrient for brain function. While VK involvement in the brain has not been fully explored, it is well-known that oxidative stress plays a critical role in neurodegenerative diseases. It was recently reported that VK protects neurons and oligodendrocytes from oxidative injury and rescues Drosophila from mitochondrial defects associated with Parkinson's disease. In this study, we take a chemical approach to define the optimal and minimum pharmacophore responsible for the neuroprotective effects of VK. In doing so, we have developed a series of potent VK analogues with favorable drug characteristics that provide full protection at nanomolar concentrations in a well-defined model of neuronal oxidative stress. Additionally, we have characterized key cellular responses and biomarkers consistent with the compounds' ability to rescue cells from oxidative stress induced cell death.

Synthesis and antiplatelet, antiinflammatory and antiallergic activities of 2,3-disubstituted 1,4-naphthoquinones

Modification of 2-acetamido-3-chloro-1,4-naphthoquinone, which has potent antiplatelet, antiallergic and antiinflammatory activities, led to a series of 2,3-disubstituted 1,4-naphthoquinones. Some of these compounds showed significant antiplatelet, antiallergic and antiinflammatory activities. Among them, 2-methoxy-3-chloro-1,4-naphthoquinone (15) and 2- ethoxy-3-chloro-1,4-naphthoquinone (17) exhibited potent inhibitory effects on neutrophil and mast cell degranulation. 2-Methoxy-1,4-naphthoquinone (20) and 2-ethoxy-1,4-naphthoquinone (21) exhibited potent inhibitory effect on neutrophil superoxide formation. These four compounds were thus selected for further evaluation.