114479-07-1

Basic information

• Product Name: 1,4-Naphthalenedione, 2-amino-3-(4-methylphenyl)-
• CAS NO: 114479-07-1
• Molecular Formula: C17H13NO2
• Molecular Weight: 263.296
• Mol File: 114479-07-1.mol

Chemical Properties

• CAS DataBase Reference: 1,4-Naphthalenedione, 2-amino-3-(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Naphthalenedione, 2-amino-3-(4-methylphenyl)-(114479-07-1)
• EPA Substance Registry System: 1,4-Naphthalenedione, 2-amino-3-(4-methylphenyl)-(114479-07-1)

Safety Data

• Hazardous Substances Data: 114479-07-1(Hazardous Substances Data)

Usage

General Description

1,4-Naphthalenedione, 2-amino-3-(4-methylphenyl)-, also known as 2-amino-3-(p-tolyl)naphthoquinone, is a chemical compound that belongs to the class of naphthoquinones. It is a yellow crystalline solid that is commonly used in the synthesis of dyes and pigments. 1,4-Naphthalenedione, 2-amino-3-(4-methylphenyl)- has potential applications in the field of medicinal chemistry, as it exhibits anti-inflammatory and analgesic properties. Additionally, it has been studied for its potential role in the treatment of various diseases, including cancer and infectious diseases. The compound is also known for its ability to undergo redox reactions, which makes it useful in the development of redox-active materials and organic electronic devices. However, it is important to handle 1,4-Naphthalenedione, 2-amino-3-(4-methylphenyl)- with care, as it may pose a risk to human health and the environment.

Upstream product

• 2348-81-4 2-amino-1,4-naphthoquinone 
• 130-15-4 [1,4]naphthoquinone 
• 15875-51-1 2-(4-methyl-benzylidene)-indan-1,3-dione 
• 539-44-6 N-4-methylphenylhydrazine 

Relevant articles and documents

P2X7 receptor inhibition by 2-amino-3-aryl-1,4-naphthoquinones

Extracellular ATP activates purinergic receptors such as P2X7, cationic channels for Ca2+, K+, and Na+. There is robust evidence of the involvement of these receptors in the immune response, so P2X7 receptors (P2X7R) are considered a potential therapeutic target for the development of anti-inflammatory drugs. Although there are many studies of the anti-inflammatory properties of naphthoquinones, these molecules have not yet been explored as P2X7 antagonists. In previous work, our group prepared 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones and studied their action on P2X7R. In this paper, eight 2-amino-3-aryl-1,4-naphthoquinones were evaluated to identify the inhibitory activity on P2X7R and the toxicological profile. Three analogues (AD-4CN, AD-4Me, and AD-4F) exhibited reduced toxicity for mammalian cells with CC50 values higher than 500 μM. These three 3-substituted 2-amino-1,4-naphthoquinones inhibited murine P2X7R (mP2X7R) in vitro. However, the analogues AD-4CN and AD-4Me showed low selectivity index values. AD-4F inhibited both mP2X7R and human P2X7R (hP2X7R) with IC50 values of 0.123 and 0.93 μM, respectively. Additionally, this analogue exhibited higher potency than BBG at inhibiting the ATP-induced release of IL-1β in vitro. Carrageenan-induced paw edema in vivo was reversed for AD-4F with an ID50 value of 11.51 ng/kg. Although AD-4F was less potent than previous 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones such as AN-04 in vitro, this 3-substituted 2-amino-1,4-naphthoquinone revealed higher potency in vivo to reduce the edematogenic response. In silico analysis suggests that the binding site of the novel 2-amino-3-aryl-1,4-naphthoquinone derivatives, including all the tautomeric forms, is located in the pore area of the hP2X7R model. Based on these results, we considered AD-4F to be a satisfactory P2X7R inhibitor. AD-4F might be used as a scaffold structure to design a novel series of inhibitors with potential inhibitory activity on murine (mP2X7R) and human (hP2X7R) P2X7 receptors.

Aryl-free radical-mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application toward the synthesis of benzocarbazoledione

Oxidative arylation of naphthoquinones has been developed through combination of o-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor-antibiotic precursor such as benzocarbazoledione.