14422-99-2

Usage

Molecular structure

A synthetic dye molecule with a naphthalene ring fused to an amide group, with an ethylamine group attached to the amino end.

Use in immunology research

A hapten used to induce contact hypersensitivity, making it useful for studying the mechanisms of allergic contact dermatitis.

Property of forming covalent adducts

DNFB can form covalent adducts with proteins, leading to the activation of the immune system and the production of specific T cells.

Potency as a sensitizer

DNFB is a potent sensitizer and has been used in animal models to study T cell-mediated immune responses.

Value in treatment development

The study of DNFB helps in understanding and developing treatments for allergic reactions.

Upstream product

• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 109-89-7 diethylamine 
• 4053-51-4 2-acetylamino-1,4-benzoquinone 
• 121-44-8 triethylamine 
• 75-04-7 ethylamine 
• 130-15-4 [1,4]naphthoquinone 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 557-66-4 ethanamine hydrochloride 

Downstream Products

• 1567382-71-1 2-(ethylamino)-3-phenylnaphthalene-1,4-dione 

Relevant academic research and scientific papers

Synthesis and characterization of 2-(n-alkylamino)-1,4-napthoquinone: Molecular structures of ethyl and hexyl derivatives

We would like to introduce seven analogues of 2-(n-alkylamino)-1,4-napthoquinone (where n-alkyl is methyl in LH-1, ethyl in LH-2, propyl in LH-3, butyl in LH-4, pentyl in LH-5, hexyl in LH-6 and heptyl in LH-7). All the said analogues have been successfully synthesized from 1,4-naphthoquinone and well characterised using different spectroscopic techniques. Furthermore, in order to understand the mechanistic aspects of formation of LH-1-LH-7 compounds we could propose the mechanism. The FT-IR spectroscopic analysis of LH-1-LH-7 compounds indicating that the presence of characteristic band of NH group at ～3340 cm-1. This band could assigned to existence of intramolecular hydrogen bonding interactions. The 13C-NMR spectroscopic technique has been used to study structural feature of LH-1-LH-7 compounds via HSQC, COSY and DEPT experiments. Finally, the structural aspects of the LH-2-LH-6 compounds have been confirmed by single crystal X-ray diffraction studies. We could observed that LH-2 compound crystallises in monoclinic space group P21/c, whereas LH-6 crystallises in triclinic P-1 space group. The molecule of LH-2 and LH-6 compounds forms dimers via NH?O hydrogen bonding interaction while polymeric chains of dimers have been seen via CH?O hydrogen bonding. It is very interesting to note that the molecules of LH-6 possessing a π-π stacking interaction between C?N of the neighbouring chains.

Tertiary amines as vinyl source for the formations of aryl or pyrrole ring on amido-substitued 1,4-quinone with the assistance of palladium salt

The one-pot synthesis of 3-isopropyl-6-methyl-1H-benzo[f]indole-4,9-dione (3e), N-(4-[isopentylamino]-3,6-dioxocyclohexa-1,4-dien-1-yl)acetamide (4d), 2-(isopentylamino)-6-methylnaphthalene-1,4-dione (5b), and 2-(4-acetamido-3,6-dioxocyclohexa-1,4-dien-1-

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.

Bifunctionalisation of 1,4-naphthoquinone by the oxidative addition of an alkylamine and iodine

Novel 2-iodo-3-(alkylamino) naphthalene-1,4-diones are formed in 33-70% yield by the reaction of alkylamine and 1, 4-naphthoquinone in the presence of iodine.

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, antibacterial and antifungal activity of 2-amino-1,4- naphthoquinones using silica-supported perchloric acid (HClO4- SiO2) as a mild, recyclable and highly efficient heterogeneous catalyst

Perchloric acid adsorbed on silica gel (1 mol%) has been found to be an efficient and recyclable heterogeneous catalyst for rapid conjugate addition of primary and secondary amines with 1,4-naphthoquinone to afford 2-amino-1,4-naphthoquinones under ultrasonication in moderate to high yields without using any solvent. The compounds tested for in vitro antimicrobial activity have shown high antibacterial activity against Gram positive bacteria Bacillus subtilis, Micrococcus luteus, Staphylococcus aureus as compared to Gram negative bacteria Burkholderia cepacia, Escherichia coli, Enterobacter cloacae, Klebseilla pneumoniae and Pseudomonas aeruginosa. High antifungal activity has been observed against Candida albicans and Issatchenkia orientalis for all the compounds.

Synthesis and screening of substituted 1,4-naphthoquinones (NPQs) as antifilarial agents

Eleven amino-substituted 1,4-naphthoquinones were synthesized via the reaction of 1,4-naphthoquinone with different primary and secondary mono- and diamines in the presence of dichloromethane ethanol (1:2) solvent at room temperature. All compounds were p

Independent Synthesis of the Violet Dyes and of a By-product Formed in the Reaction of 1,2-Naphthoquinone-4-sulfonic Acid with Primary Aliphatic Amines

4-Dimethylamino-1,2-naphthoquinone (8) and 2-dimethylamino-1,4-naphthoquinone (10) are O-methylated by methyl fluorosulfonate to form the stable iminium salts 9 and 11.In analogous way the 2-alkylamino-1,4-naphthoquinones 13 were transformed into the iminium salts 14.These salts condense with 3-amino-4-hydroxynaphthalene-1-sulfonic acid (15) to give the violet 3--4-hydroxynaphthalene-1-sulfonic acids 2.The iminium salt 14c reacts with benzylamine to yield the vinylogous amidinium salt 19, which is oxidised by silver oxide inpyridine to give the N-benzylidene-2-phenyl-5-naphthoxazolamine 20.Reduction of 20 with LiAlH4 leads to the formation of N-benzyl-2-phenyl-5-naphthoxazolamine (7).

Naphthoquinone Colouring Matters. Part 6. Colour and Constitution of Electron Donor-substituted 2-Aryl- and 2-Vinyl-1,4-naphthoquinones.

The visible absorption spectroscopic properties of 2-aryl-1,4-naphthoquinones containing amino-groups in the 4'-position of the aryl ring or in the 3-position of the quinonoid ring, and also of the related 2-aminovinyl-1,4-naphthoquinones, are described.P