17672-02-5

Basic information

• Product Name: 4-[methyl(phenyl)amino]naphthalene-1,2-dione
• CAS NO: 17672-02-5
• Molecular Formula: C₁₇H₁₃NO₂
• Molecular Weight: 263.2906
• Mol File: 17672-02-5.mol

Chemical Properties

• Boiling Point: 418.3°C at 760 mmHg
• Flash Point: 187.2°C
• Density: 1.29g/cm³
• Vapor Pressure: 3.32E-07mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 4-[methyl(phenyl)amino]naphthalene-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[methyl(phenyl)amino]naphthalene-1,2-dione(17672-02-5)
• EPA Substance Registry System: 4-[methyl(phenyl)amino]naphthalene-1,2-dione(17672-02-5)

Safety Data

• Hazardous Substances Data: 17672-02-5(Hazardous Substances Data)

Upstream product

• 135-19-3 β-naphthol 
• 524-42-5 1,2-naphthoquinone 
• 100-61-8 N-methylaniline 
• 521-24-4 sodium 1,2-naphthoquinone-4-sulfonate 

Downstream Products

• 83-72-7 2-hydroxynaphtho-1,4-quinone 

Relevant articles and documents

Selective Inhibitors of Human Liver Carboxylesterase Based on a β-Lapachone Scaffold: Novel Reagents for Reaction Profiling

Carboxylesterases (CEs) are ubiquitous enzymes that are responsible for the metabolism of xenobiotics, including drugs such as irinotecan and oseltamivir. Inhibition of CEs significantly modulates the efficacy of such agents. We report here that β-lapachone is a potent, reversible CE inhibitor with Ki values in the nanomolar range. A series of amino and phenoxy analogues have been synthesized, and although the former are very poor inhibitors, the latter compounds are highly effective in modulating CE activity. Our data demonstrate that tautomerism of the amino derivatives to the imino forms likely accounts for their loss in biological activity. A series of N-methylated amino derivatives, which are unable to undergo such tautomerism, were equal in potency to the phenoxy analogues and demonstrated selectivity for the liver enzyme hCE1. These specific inhibitors, which are active in cell culture models, will be exceptionally useful reagents for reaction profiling of esterified drugs in complex biological samples.

O-Iodoxybenzoic Acid-Initiated One-Pot Synthesis of 4-Arylthio-1,2-naphthoquinones, 4-Arylthio-1,2-diacetoxynaphthalenes, and 5-Arylthio-/5-Aminobenzo[a]phenazines

1,2-Naphthoquiones and their derivatives constitute an important category of compounds of relevance in pharmaceutical and material chemistry. It is shown that 1,2-naphthoquinones generated by o-iodoxybenzoic acid-mediated oxidation of 2-naphthols can be subjected to a cascade of reactions, namely oxidation, Michael addition, reduction, acetylation, and cyclocondensation, in the same pot to afford diverse 4-arylthio-1,2-naphthoquinones 2, 4-arylthio-1,2-diacetoxynaphthalenes 3, and 5-arylthio-/5-aminobenzo[a]phenazines 4 in very good isolated yields. The multistep single-pot synthesis occurs smoothly in DMF at rt.

HEAT SHOCK PROTEIN 90 INHIBITORS, METHODS OF PREPARING SAME, AND METHODS FOR THEIR USE

Novel classes of molecular chaperone Heat shock protein 90 (Hsp90) inhibitors are disclosed. These compounds are useful in treating and preventing cancer and other Hsp90-related diseases and conditions, such as inflammation and neurodegenerative disorders. Methods of treating and preventing cancer and other Hsp90 related diseases and conditions are disclosed that include administering to the subject a therapeutically effective amount of an Hsp90 inhibitor. Methods of preparing the novel Hsp90 inhibitors are also provided.

Synthesis and PTP1B inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents.

A new series of 1,2-naphthoquinone derivatives was synthesized by various synthetic methods and evaluated for their ability to inhibit protein tyrosine phosphatase 1B (PTP1B). 1,2-Naphthoquinone derivatives with substituent at R(4) position showed submicromolar inhibitory activity, and compound 24 demonstrated 10- to 60-fold selectivity against the tested phosphatases. Also, several 4-aryl-1,2-naphthoquinone derivatives with substituents at R(3), R(6), R(7), or/and R(8) showed submicromolar inhibitory activity and good plasma stability.

The Effect of Metal Chelate Complexation on the Reactivity and Absorption Spectra of 1,2-Naphthoquinones: New Types of Near-infrared-absorbing Metal Complex Dyes

The reaction of sodium 1,2-naphthoquinone-4-sulphonate with various arylamines and 1,1-bisethylene were effectively promoted by nickel(II) ion to give 4-aminated, 4-arylated, and 4-vinylated 1,2-naphthoquinones in good yield.The f