22266-99-5

Usage

Uses

Used in Pharmaceutical Industry:
5-methoxy-2-methylnaphthoquinone is used as an intermediate in the synthesis of Plumbagin-d3 (P627002), a compound that has been shown to induce apoptosis in cancer cells. This makes it a valuable component in the development of anticancer drugs.
Used in Research Applications:
5-methoxy-2-methylnaphthoquinone is also used as a research tool for studying the effects of Plumbagin and its derivatives on various cellular processes. It can be employed in experiments to investigate the mechanisms of apoptosis induction and the inhibition of NADPH oxidase 4, which may provide insights into the development of novel therapeutic strategies for cancer treatment.

InChI:InChI=1/C12H10O3/c1-7-6-9(13)11-8(12(7)14)4-3-5-10(11)15-2/h3-6H,1-2H3

Upstream product

• 79795-25-8 1-Hydroxy-5-methoxy-2-methylnaphthalin 
• 4923-61-9 5-methoxynaphthoquinone 
• 67-68-5 dimethyl sulfoxide 
• 481-42-5 5-hydroxy-2-methyl-1,4-naphthoquinone 
• 74-88-4 methyl iodide 
• 3588-80-5 5-methoxynaphthalen-1-ol 
• 578-57-4 2-bromoanisole 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 83-56-7 1,5-dihydroxynaphthalene 
• 481-40-3 1,4,5-trihydroxynaphthalene 
• 86309-89-9 2,2-Dimethylnaphtho<1,8-de><1,3>dioxin-6-ol 
• 138719-99-0 2-iodo-3-methoxyphenol trifluoromethanesulfonate 
• 94930-41-3 7-methoxy-3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 
• 80-62-6 methacrylic acid methyl ester 

Downstream Products

• 481-42-5 5-hydroxy-2-methyl-1,4-naphthoquinone 
• 1286232-68-5 5-methoxy-2-methyl-3-(4-(trifluoromethyl)benzylamino)naphthalene-1,4-dione 
• 1286232-67-4 5-methoxy-3-(4-methoxybenzylamino)-2-methylnaphthalene-1,4-dione 
• 1286232-64-1 3-(allylamino)-5-methoxy-2-methylnaphthalene-1,4-dione 
• 1286232-66-3 3-(4-fluorobenzylamino)-5-methoxy-2-methylnaphthalene-1,4-dione 
• 1286232-65-2 3-(benzylamino)-5-methoxy-2-methylnaphthalene-1,4-dione 
• 1620126-85-3 2-methyl (2-(1,4-dihydro-5-methoxy-2-methy-1,4-dioxonaphthalen-3-ylthio)acetamido)-3-phenylpropanoate 

Relevant academic research and scientific papers

Novel juglone and plumbagin 5-O derivatives and their in vitro growth inhibitory activity against apoptosis-resistant cancer cells

Juglone 1 an plumbagin 2 are plant secondary metabolites nowadays well known for their anticancer properties. In this study we synthesized analogues of 1 and 2 deriving from the functionalization of the OH group in position 5 with different side chains in form of esters and ethers. Therefore the growth inhibitory activities of these adducts were evaluated in vitro on six cancer cell lines using the MTT colorimetric assays along with the two natural parent compounds. The data revealed that these latter displayed the strongest growth inhibitory activities in vitro. Quantitative videomicroscopy analyses were then carried out on human U373 glioblastoma cells, which are characterized by various level of resistance to pro-apoptotic stimuli. We compared the naturally occurring reference compounds 1 and 2 with the derivatives exerting the best activities in terms of IC50 growth inhibitory values. These analyses showed that both juglone and plumbagin had a cytostatic effect on U373 cells and were able to overcome the intrinsic resistance of U373 cancer cells to pro-apoptotic stimuli.

Antimalarial naphthoquinones from Nepenthes thorelii

Roots of Nepenthes thorelii yielded plumbagin, 2-methylnaphthazarin, octadecyl caffeate, isoshinanolone, and droserone. In addition, seven derivatives were prepared from plumbagin. Each of these natural and semisynthetic compounds was evaluated for in vitro antimalarial potential.

Synthesis of 2-Alkyl-1,4-naphthoquinones via an ortho-Directive Metalation

Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) has been shown to have a potent insect ecdysis inhibitory activity.To test the activity of synthetic analogs, the synthesis of 2-alkyl-1,4-naphthoquinones via an ortho-directive metalation using naphthol methoxymethyl ether as a directive group was carried out.This method is also applicable to the synthesis of naphthoquinones having unsaturated side-chain.

Bisketene Equivalents as Diels-Alder Dienes

2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.

Highly Efficient Synthesis and Structure–Activity Relationships of a Small Library of Substituted 1,4-Naphthoquinones

A platform of highly efficient synthetic methodologies has been established to access a focused library of substituted 1,4-naphthoquinones derivatives functionalized with a diversity of amino/hydroxy/alkyl groups. Furthermore, the structure–activity relationship deduced from antiproliferative activities and toxicities of this 1,4-naphthoquinone library and intracellular reactive oxygen species (ROS) level detections might warrant future potential of plumbagin (2) and compound 13 as promising basic structures to develop novel anti-cancer agents.

Rhodium-catalyzed C-H bond activation for the synthesis of quinonoid compounds: Significant Anti-Trypanosoma cruzi activities and electrochemical studies of functionalized quinones

Thirty four halogen and selenium-containing quinones, synthesized by rhodium-catalyzed C-H bond activation and palladium-catalyzed cross-coupling reactions, were evaluated against bloodstream trypomastigotes of T.?cruzi. We have identified fifteen compounds with IC50/24?h values of less than 2?μM. Electrochemical studies on A-ring functionalized naphthoquinones were also performed aiming to correlate redox properties with trypanocidal activity. For instance, (E)-5-styryl-1,4-naphthoquinone 59 and 5,8-diiodo-1,4-naphthoquinone 3, which are around fifty fold more active than the standard drug benznidazole, are potential derivatives for further investigation. These compounds represent powerful new agents useful in Chagas disease therapy.

COMPOSITIONS AND METHODS FOR TREATMENT OF PROSTATE CARCINOMA

Disclosed herein are 1,4-naphthoquinone analogs, pharmaceutical compositions that include one or more of such 1,4-naphthoquinone analogs, and methods of treating and/or ameliorating diseases and/or conditions associated with a cancer, such as prostate can

Synthesis of Vitamin K and Related Naphthoquinones via Demethoxycarbonylative Annulations and a Retro-Wittig Rearrangement

Anionic annulations of 3-nucleofugal phthalides with α-alkyl(aryl)acrylates involving a demethoxycarbonylation provide a succinct synthesis of vitamin K and related naphthoquinones. Also reported is a new cascade reaction stemming from a Cope-retro-Wittig rearrangement. This cascade leads to direct formation of 1-hydroxy-4-prenyloxynaphthalene-2-carboxylates from the corresponding α-prenyl acrylate acceptors.

Tetracycline analogues with a selective inhibitory effect on HIF-1α

As part of a programme to discover novel transcription factor inhibitors, a 40-membered library of tetracycline analogues was screened to identify potential HIF-1 inhibitors. Two novel analogues (5b and 5c) with significant HIF-1 modulation properties were identified. These molecules possess good cellular penetration properties, and provide significant down-regulation of VEGF in U251 cells.

Synthesis and SAR study of novel anticancer and antimicrobial naphthoquinone amide derivatives

A series of novel naphthoquinone amide derivatives of the bioactive quinones, plumbagin, juglone, menadione and lawsone, with various amino acids were synthesized. The compounds were characterized by 1H NMR, 13C NMR, Mass, IR and ele