1620161-59-2

Basic information

• Product Name: 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione
• Synonyms: 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione
• CAS NO: 1620161-59-2
• Molecular Weight: 400.39
• Mol File: 1620161-59-2.mol

Chemical Properties

• CAS DataBase Reference: 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione(1620161-59-2)
• EPA Substance Registry System: 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione(1620161-59-2)

Safety Data

• Hazardous Substances Data: 1620161-59-2(Hazardous Substances Data)

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 100-52-7 benzaldehyde 
• 100-01-6 4-nitro-aniline 

Relevant articles and documents

Facile synthesis of aminonaphthoquinone Mannich bases by noncatalytic multicomponent reaction

Mannich bases are formed in a noncatalytic multicomponent reaction, which is promoted by ultrasound irradiation. The procedure avoids the use of toxic solvents, catalyst, and purification, generating the desired compounds in excellent yields and short reaction times.

Design, synthesis, and catalytic performance of modified graphene oxide based on a cobalt complex as a heterogenous catalyst for the preparation of aminonaphthoquinone derivatives

We are reporting a functionalized graphene oxide catalyst developed by modifying graphene oxide surface using the covalent attachment of an amino-functionalized SiO2sphere/cobalt complex. Silica network has special characteristics including mechanical strength, high thermal and chemical stability with good dispersion in solvents. The silica/graphene oxide mixture provides improved properties and extends the scope of application. Graphene oxide was functionalized by spherical silica with the help of hybrid silane-containing nitrogen to coordinate with Co(ii) for increasing the catalytic activity. The catalyst was characterized by Fourier Transform Infrared (FT-IR) spectroscopy, powder X-ray diffraction (XRD), Energy Dispersive X-ray (EDX), Scanning Electron Microscopy (SEM), Raman spectroscopy, and Thermal Gravimetric (TGA) analyses. The catalyst showed high catalytic activity for multi-component reactions in the synthesis of aminonaphthoquinones in ethanol solvent. The catalyst's ability to improve the yield (96-98%), reduce the reaction time (5-8 min), and recycling ability are important benefits for the catalyst.

Synthesis, in vitro antifungal activity and molecular modeling studies of new Mannich bases derived from lawsone

Hydroxynaphthoquinones such as lawsone (2-hydroxy-1,4-naphthoquinone) have proven to be effective antifungal agents. These compounds were tested for antifungal activity against yeast standard and clinical strains by the broth microdilution method. Among the synthetic lawsone derivatives, 2-hydroxy-3-((2-hydroxyphenyl)(pyrrolidin-1-yl)methyl)naphthalene-1,4-dione, 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione and 2-hydroxy-3-((2-hydroxyphenyl)((4-nitrophenyl)amino)methyl)naphthalene-1,4-dione showed high activity against Candida albicans ATCC 10231, with minimal inhibitory concentrations (MICs) and minimal fungicidal concentrations (MFCs) ranging from 20 to 330 and from 80 to 330 μg mL-1, respectively. Moreover, they also showed a mechanism of action on exogenous ergosterol. Therapeutic concentrations (CC50) of 2-hydroxy-3-((2-hydroxyphenyl)(pyrrolidin-1-yl)methyl) naphthalene-1,4-dione, 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione and 2-hydroxy-3-((2-hydroxyphenyl)((4-nitrophenyl)amino)methyl)naphthalene-1,4-dione were 52.81, 52.58 and 85.94 μg mL-1, respectively, which can be considered moderate or low. In addition, docking studies showed that these compounds had similar binding energy to standard ketoconazole, which are recognized as the molecular target by van der Waals interactions. Furthermore, they are under Lipinski's rule of 5 with a druglikeness score better than ketoconazole and nystatin. These findings suggest that 2-hydroxy-3-((2-hydroxyphenyl)(pyrrolidin-1-yl)methyl) naphthalene-1,4-dione, 2-hydroxy-3-(((4-nitrophenyl)amino)(phenyl)methyl)naphthalene-1,4-dione and 2-hydroxy-3-((2-hydroxyphenyl)((4-nitrophenyl)amino)methyl)naphthalene-1,4-dione have potential as leading compounds against human fungal infections.

A simple and convenient method for synthesis of new aminonaphthoquinones derived from lawsone by catalytic multicomponent Mannich reaction

A clean, efficient and facile one-pot protocol was developed for the synthesis of a series of new aminonaphthoquinones derived from 2-hydroxy-1,4-naphthoquinone (lawsone) by three-component Mannich reaction using catalytic amount of p-TsOH in CH3CN, at room temperature. At the present work, we improved the yield and significantly reduced the reaction time for several Mannich reactions with different amine and aromatic aldehydes using a non-expensive, mild catalyst and suitable solvent.