1090-16-0

Usage

Uses

Used in Pharmaceutical Industry:
3-anilino-2-chloro-1,4-naphthoquinone is used as a precursor in the synthesis of pharmaceuticals due to its unique chemical structure and potential biological activities. Its presence in the synthesis process can contribute to the development of new drugs with specific therapeutic properties.
Used in Antibacterial Applications:
3-anilino-2-chloro-1,4-naphthoquinone is used as an antibacterial agent for its potential to combat bacterial infections. Its chemical structure allows it to interact with bacterial cells, inhibiting their growth and potentially leading to their destruction.
Used in Antifungal Applications:
3-anilino-2-chloro-1,4-naphthoquinone is used as an antifungal agent, leveraging its chemical properties to target and inhibit the growth of fungi, making it a candidate for treating fungal infections.
Used in Cancer Research:
3-anilino-2-chloro-1,4-naphthoquinone is used as an anticancer agent in research settings, where it has shown promise in targeting and affecting the viability of cancer cells. Its potential to modulate cellular processes and induce cell death makes it an interesting compound for further exploration in oncology.
Used in Dye Industry:
3-anilino-2-chloro-1,4-naphthoquinone is used as a dye in various applications due to its color-producing properties. Its chemical structure allows it to be incorporated into materials that require coloration, such as textiles, paints, and other industrial products.

InChI:InChI=1/C16H11ClN2O2/c17-13-14(19-18-10-6-2-1-3-7-10)16(21)12-9-5-4-8-11(12)15(13)20/h1-9,18-19H

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 64-17-5 ethanol 
• 62-53-3 aniline 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 110-86-1 pyridine 
• 16867-03-1 2-amino-3-hydroxypyridine 
• 4497-73-8 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-phenylacetamide 
• 95-55-6 2-amino-phenol 
• 589-09-3 N-allyl-N-phenylamine 
• 98-95-3 nitrobenzene 
• 7647-01-0 hydrogenchloride 
• 303159-24-2 2-anilino-3-chloro-[1,4]naphthoquinone-4-phenylimine 
• 104307-23-5 2-phenylimino-3,3-dichloro-2,3-dihydro-1,4-naphthoquinone 
• 6628-97-3 2-(phenylamino)naphthoquinone 

Downstream Products

• 4497-73-8 N-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-phenylacetamide 
• 60598-36-9 6-anilino-9-chloro-benzo[a]phenothiazin-5-one 
• 60598-41-6 6-anilino-9-ethoxy-benzo[a]phenothiazin-5-one 
• 60598-39-2 6-anilino-9-methyl-benzo[a]phenothiazin-5-one 
• 104307-23-5 2-phenylimino-3,3-dichloro-2,3-dihydro-1,4-naphthoquinone 
• 488128-98-9 2-chloro-3-[(2,4-dinitrophenyl)amino]-1,4-naphthoquinone 
• 868562-63-4 C₃₂H₂₀N₂O₄S₂ 
• 61770-44-3 2-anilino-3-methylsulfanyl-[1,4]naphthoquinone 
• 1171120-73-2 2-(naphthalene-1-ylthio)-3-(phenylamino)naphthalene-1,4-dione 
• 1171120-72-1 2-(3-methoxyphenylthio)-3-(phenylamino)naphthalene-1,4-dione 
• 72520-46-8 2-phenylamino-3-(phenylthio)naphthalene-1,4-dione 
• 1315212-66-8 4,9-dioxo-1-phenyl-1H-naphtho[2,3-d][1,2,3]triazole 2-oxide 
• 1315212-70-4 2-[(1-phenyl-1H-1,2,3-triazol-4-yl-2-oxide)carbonyl]benzoic acid 
• 54941-03-6 2-hydroxy-3-(phenylamino)naphthalene-1,4-dione 

Relevant academic research and scientific papers

Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents

Several members of the phenylamino-1,4-naphthoquinone series were prepared in order to investigate structure-activity relationships (SAR) and to explore the antitumor effects associated with this scaffold. The cytotoxic effects of the aminoquinones (ECsu

Substituted 1,4-Naphthoquinones vs. the Ascitic Sarcoma 180 of Mice

Twelve 1,4-naphthoquinones have been tested against the ascitic form of sarcoma 180 in Swiss mice.Statistical analysis shows that the most important molecular parameter determining their effectiveness in prolonging the life of mice bearing this tumor is their redox potentials.Although the toxicities of the compounds are also related to the redox potentials in the same way, the therapeutic indexes can be increased by adding substituents of greater lipophilicity.The naphthoquinones differ greatly in antitumor activities and may inhibit the growth of malignant cells by different mechanisms

Synthesis and characterization of nitrogen and sulfur containing 1,4-naphthoquinones

New N,S-disubstituted naphthoquinones were synthesized by reactions of S- and N-nucleophiles with 2,3-dichloro-1,4-naphthoquinone. 2-(Hexadecylthio)-3- (phenylamino)-naphthalene-1,4-dione 5a was synthesized by reaction of 2-chloro-3-(phenylamino)-naphthal

Crystallographic evidence for resonance assisted H-Bonding effect in selective colorimetric detection of cyanide by arylamino-naphthoquinones

Five new chemo-receptors, based on arylamino-naphthoquinone, possessing electron donating and electron withdrawing substituents have been prepared by single step green method. These receptors are found to be highly selective and sensitive towards cyanide

Synthesis, antimicrobial properties, and inhibition of catalase activity of 1,4-naphtho-and benzoquinone derivatives containing N-, S-, O-substituted

A series of new 1,4-naphtho-and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving

Synthesis and Antimicrobial Evaluation of 1,4-Naphthoquinone Derivatives as Potential Antibacterial Agents

1,4-Naphthoquinones are an important class of compounds present in a number of natural products. In this study, a new series of 1,4-naphthoquinone derivatives were synthesized. All the synthesized compounds were tested for in vitro antimicrobial activity.

Spectroscopic and theoretical studies on the nucleophilic substitution of 2,3-dichloronaphthoquinone with para-substituted anilines in solid state via initial charge transfer complexation

Various spectroscopy techniques (UV-Vis, DRS, FT-IR, 1H NMR, LC-MS) and theoretical computations have been employed to investigate the mechanism of the nucleophilic substitution reaction of 2,3- dichloronaphthoquinone (DCNQ) with para-substitut

Synthesis of novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone

Several novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone have been synthesized in good to excellent yields. First, 2-chloro-3-(2,4-dinitroanilino)-1,4-naphthoquinone was prepared in two steps beginning with the reaction of

Thermolysis of 2-azido-3-(R-anilino)-1,4-naphthoquinones. Nitrene insertion versus hydrogen abstraction

2-chloro-3-(R-anilino)-1,4-naphthoquinones react with sodium azide upon refluxing in DMF. The thermochemistry of 2-azido-3-(R-anilino)-1,4-naphthoquinone is strongly modified by the substituent on aniline. Having an strong electron-donor like O-R results

Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON)

Leber's hereditary optic neuropathy (LHON) is a rare genetic mitochondrial disease and the primary cause of chronic visual impairment for at least 1 in 10 ?000 individuals in the U.K. Treatment options remain limited, with only a few drug candidates and therapeutic approaches, either approved or in development. Recently, idebenone has been investigated as drug therapy in the treatment of LHON, although evidence for the efficacy of idebenone is limited in the literature. NAD(P)H:quinone oxidoreductase 1 (NQO1) and mitochondrial complex III were identified as the major enzymes involved in idebenone activity. Based on this mode of action, computer-aided techniques and structure-activity relationship (SAR) optimization studies led to the discovery of a series naphthoquinone-related small molecules, with comparable adenosine 5′-triphosphate (ATP) rescue activity to idebenone. Among these, three compounds showed activity in the nanomolar range and one, 2-((4-fluoro-3-(trifluoromethyl)phenyl)amino)-3-(methylthio)naphthalene-1,3-dione (1), demonstrated significantly higher potency ex vivo, and significantly lower cytotoxicity, than idebenone.