4923-61-9

Usage

InChI:InChI=1/C11H8O3/c1-14-10-4-2-3-7-8(12)5-6-9(13)11(7)10/h2-6H,1H3

Upstream product

• 3588-80-5 5-methoxynaphthalen-1-ol 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 74-88-4 methyl iodide 
• 3588-75-8 8-methoxy-naphthalen-1-ol 
• 64636-39-1 1,4,5-Trimethoxynaphthalene 
• 3843-55-8 4,8-dimethoxy-1-naphthol 
• 24000-38-2 1,4-dimethoxy-1,3-butadiene 
• 106-51-4 p-benzoquinone 
• 93087-44-6 1-Methoxy-1,4-ethano-1,4-dihydro-naphthalindion-(5,8) 
• 860776-15-4 1-hydroxy-4,5-naphthylene phenylboronate 
• 186581-53-3 diazomethane 
• 42907-97-1 1-methoxy-4,5-naphthylene diacetate 
• 481-40-3 1,4,5-trihydroxynaphthalene 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 159497-29-7 N-(2-methoxy-4-methlphenyl)-3-amino-5-methoxy-1,4-napthoquinone 
• 129237-15-6 1-(N-Benzoyl-N-benzylamino)-5-methoxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone 
• 3300-25-2 8-O-methylchrysophanol 
• 76695-93-7 1-hydroxy-5-methoxy-3-methyl-9,10 dihydroanthracene 9,10-dione 
• 22266-99-5 2-methyl-5-methoxy-1,4-naphthoquinone 
• 22273-29-6 8-methoxy-2-methylnaphthalene-1,4-dione 
• 90013-25-5 5-methoxy-2,3-dimethyl-1,4-naphtoquinone 
• 109696-97-1 5-methoxy-3-(p-tolylthio)-1,4-naphthoquinone 
• 95684-16-5 2-chloro-3-anilino-5-methoxy-1,4-naphthoquinone 
• 95684-15-4 2-anilino-3-chloro-5-methoxy-1,4-naphthoquinone 
• 1201635-11-1 2-bromobenzoic acid 4-hydroxy-5-methoxynaphthalen-1-yl ester 
• 101600-87-7 8-methoxy-2-(phenylamino)-1,4-naphthoquinone 
• 1607448-12-3 C₂₈H₂₁NO₃ 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 

Relevant academic research and scientific papers

Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative

The cytotoxicity of nine naphthoquinones (NQ) was assayed against HL-60 (leukaemia), MDA-MB-435 (melanoma), SF-295 (brain) and HCT-8 (colon), all human cancer cell lines, and peripheral blood mononuclear cells (PBMC), as representatives of normal cells, after 72h of incubation. 5-Methoxy-1,4-naphthoquinone was the most active compound, showing IC50 values in the range of 0.31 (1.7μM) in HL-60 to 0.88μg/mL (4.7μM) in SF-295 and IC50 of 0.69μg/mL (3.7μM) against PBMC. With the introduction of a bromo-substituent in position 2 or 3 of juglone, the IC50 significantly decreased, regardless of the position on the NQ moiety. However, compared with juglone methyl ether, the halogen substitution decreased the activity. To further understand the mechanism underlying the cytotoxicity of 5-methoxy-1,4-naphthoquinone, studies involving DNA fragmentation, cell cycle analysis, phosphatidyl serine externalization, mitochondrial depolarization and activation of caspases 8 and 3/7 were performed in HL-60 cell line, using doxorubicin as a positive control. The results indicate that the cytotoxic 5-methoxy-1,4-naphthoquinone activates caspases 8 and 3/7 and thus induces apoptosis independent of mitochondria.

Coccidiostatic agents: Synthesis of some analogs of (±)-frenolicin B

Starting from juglone derivative 5, a series of frenolicin B analogs 15 (R1 = R2 = Me), 19a (R1 = H, R2 = Ph), and 19b (R1 = Ph, R2 = H) were obtained via the key β-hydroxy ester intermedia

Carbocyclic frenolicin analogues: Novel anticoccidial agents

Carbocyclic analogues of the antibacterial natural product frenolicin B have been synthesised. These analogues were active against parasitic protozoa of the genus Eimeria and represent a new series of anticoccidial agents. The synthesis of simplified analogues helped to define a possible pharmacophore for frenolicin.

2-Propargylamino-naphthoquinone derivatives as multipotent agents for the treatment of Alzheimer's disease

Alzheimer's disease is a progressive brain disorder with characteristic symptoms and several pathological hallmarks. The concept of “one drug, one target” has not generated any new drugs since 2004. The new era of drug development in the field of AD build

Synthesis, biological evaluation, and correlation of cytotoxicity versus redox potential of 1,4-naphthoquinone derivatives

A series of 1,4-naphthoquinone derivatives of lawsone (1), 6-hydroxy-1,4-naphthoquinone (2), and juglone (3) were synthesized by alkylation, acylation, and sulfonylation reactions. The yields of lawsone derivatives 1a-1k (type A), 6-hydroxy-1,4-naphthoqui

Synthesis and biological evaluation of novel isothiazoloquinoline quinone analogues

Natural quinones and their analogues have attracted growing attention because of their novel anticancer activities. A series of novel isothiazoloquinoline quinone analogues were synthesized and evaluated for antitumor activities against four different kind of cancer cells. Among them, isothiazoloquinolinoquinones inhibited cancer cells proliferation effectively with IC50 values in the nanomolar range, and isothiazoloquinolinoquinone 13a induced the cell apoptosis. Further exploration of possible mechanism of action indicates that 13a not only activates ROS production through NQO1-directed redox cycling but also inhibits the phosphorylation of STAT3. These findings indicate that 13a has potential use for the development of new skeleton drug candidate as an efficient substrate of NQO1 and STAT3 inhibitor.

Ruthenium(II)-Catalyzed Double Annulation of Quinones: Step-Economical Access to Valuable Bioactive Compounds

Double ruthenium(II)-catalyzed alkyne annulations of quinones were accomplished. Thus, a strategy is reported that provides step-economical access to valuable quinones with a wide range of applications. C?H/N?H activations for alkyne annulations of naphthoquinones provided challenging polycyclic quinoidal compounds by forming four new bonds in one step. The singular power of the thus-obtained compounds was reflected by their antileukemic activity.

Anti-novel coronavirus naphthoquinone compound and medical application thereof

The invention discloses an anti-novel coronavirus naphthoquinone compound and a medical application of the naphthoquinone compound. The structure of the compound is shown as a formula (I), wherein R1is hydrogen, methyl, ethyl, acetyl or propionyl; and R2 is hydrogen, methyl or ethyl. The compound disclosed by the invention has very strong activity of resisting the novel coronavirus, and can be used for inhibiting 3CL hydrolase (3C-like proteinase, 3CLpro) of the 2019-nCoV novel coronavirus. The in-vitro activity determination experiments show that the enzyme inhibition rate of part of the compounds reaches 99% under the concentration of 1 [mu] M. The naphthoquinone compound disclosed by the invention is clear in structure, simple and convenient in preparation method and high in yield, andhas important significance for developing efficient and low-toxicity novel anti-novel coronavirus drugs.

Generation of Endocyclic Vinyl Carbene Complexes via Gold-Catalyzed Oxidative Cyclization of Terminal Diynes: Toward Naphthoquinones and Carbazolequinones

Carbene cascade reactions involving carbene/alkyne metathesis have attracted much attention over the past decades because this chemistry offers great potential to build complicated cyclic molecules. However, the formed vinyl metal carbenoids in these reactions are limited to exocyclic carbenes, and the generation of endocyclic vinyl carbene complexes remains unexplored. Here, we report an unprecedented gold-catalyzed oxidative cyclization of terminal diynes. Importantly, the generation of endocyclic vinyl carbene complexes was involved in this oxidative cyclization, which is distinctively different from previous protocols. This method allows the facile synthesis of various valuable naphthoquinones and carbazolequinones from readily available diynes under exceptionally mild reaction conditions and features a broad substrate scope and wide functional group tolerance. Moreover, theoretical calculations provide further evidence on the divergent selectivity of this cyclization reaction.

Lawsone, Juglone, and β-Lapachone Derivatives with Enhanced Mitochondrial-Based Toxicity

Naphthoquinones are among the most active natural products obtained from plants and microorganisms. Naphthoquinones exert their biological activities through pleiotropic mechanisms that include reactivity against cell nucleophiles, generation of reactive oxygen species (ROS), and inhibition of proteins. Here, we report a mechanistic antiproliferative study performed in the yeast Saccharomyces cerevisiae for several derivatives of three important natural naphthoquinones: lawsone, juglone, and β-lapachone. We have found that (i) the free hydroxyl group of lawsone and juglone modulates toxicity; (ii) lawsone and juglone derivatives differ in their mechanisms of action, with ROS generation being more important for the former; and (iii) a subset of derivatives possess the capability to disrupt mitochondrial function, with β-lapachones being the most potent compounds in this respect. In addition, we have cross-compared yeast results with antibacterial and antitumor activities. We discuss the relationship between the mechanistic findings, the antiproliferative activities, and the physicochemical properties of the naphthoquinones.