29366-44-7

Usage

Derivative

1,4-naphthoquinone

Synonyms

Menadione

Category

Synthetic form of vitamin K

Uses

a. Nutritional supplement
b. Production of vitamin K supplements
c. Precursor for synthesis of dyes and pigments

Research

Potential antiproliferative and anticancer properties

Safety

Toxic in high doses, handle with caution

InChI:InChI=1/C12H10O3/c1-2-7-10(13)8-5-3-4-6-9(8)12(15)11(7)14/h3-6,13H,2H2,1H3

Upstream product

• 53948-59-7 2,3-epoxi-2-etil-2,3-dihidro-1,4-naftoquinona 
• 858436-33-6 2-ethyl-naphthalene-1,3-diol 
• 180522-51-4 2-etil-3-hidroxi-1,4-naftoquinona triacetato 
• 100121-60-6 1-(2-acetyl-phenyl)-butan-1-one 
• 51015-30-6 3-ethyl-1-oxo-1,2,3,4-tetrahydronaphthalene 
• 861087-42-5 3-ethyl-1,4-dihydroxy-[2]naphthoic acid ethyl ester 
• 861068-47-5 3,4-diacetoxy-2-acetyl-2-ethyl-2H-naphthalen-1-one 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 64-19-7 acetic acid 
• 67-56-1 methanol 
• 63688-80-2 2,3-epoxy-2,3-diethyl-2,3-dihydro-[1,4]naphthoquinone 
• 67-64-1 acetone 
• 71202-26-1 (3-Ethyl-2,4-dihydroxy-1-naphthyl)phenylmethanon 
• 3248-28-0 dipropionyl peroxide 

Downstream Products

• 483-55-6 phthiocol 
• 62830-41-5 4-{N'-[3-Ethyl-2-hydroxy-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-3-iodo-benzoic acid ethyl ester 
• 62830-36-8 4-{N'-[3-Ethyl-2-hydroxy-4-oxo-4H-naphthalen-(1Z)-ylidene]-hydrazino}-3-iodo-benzoic acid 
• 62830-32-4 2-Ethyl-3-hydroxy-4-[(2-iodo-4-methyl-phenyl)-hydrazono]-4H-naphthalen-1-one 
• 62830-28-8 2-Ethyl-3-hydroxy-4-[(4-iodo-phenyl)-hydrazono]-4H-naphthalen-1-one 

Relevant academic research and scientific papers

Synthesis and structure elucidation of oxidative coupling products of 2-hydroxy-1,4-naphthoquinones

2,3-Dihydro-3-O-(1,4-naphthoquinon-2-yl)-2-oxo-1,4-naphthoquinones are the products of oxidative coupling of substituted 2-hydroxy-1,4-naphthoquinones (regardless of the presence of peri-hydroxy groups in their structures) under the action of lead dioxide

Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies

A series of nine RuII arene complexes bearing tridentate naphthoquinone-based N,O,O-ligands was synthesized and characterized. Aqueous stability and their hydrolysis mechanism were investigated via UV/vis photometry, HPLC-MS, and density functional theory calculations. Substituents with a positive inductive effect improved their stability at physiological pH (7.4) intensely, whereas substituents such as halogens accelerated hydrolysis and formation of dimeric pyrazolate and hydroxido bridged dimers. The observed cytotoxic profile is unusual, as complexes exhibited much higher cytotoxicity in SW480 colon cancer cells than in the broadly chemo- (incl. platinum-) sensitive CH1/PA-1 teratocarcinoma cells. This activity pattern as well as reduced or slightly enhanced ROS generation and the lack of DNA interactions indicate a mode of action different from established or previously investigated classes of metallodrugs.

Organocatalytic Enantioselective Michael-Aldol[3+2] Annulation for the Synthesis of Nitro-Methanobenzo[7] annulenes

We report an enantioselective Michael-Aldol[3+2] annulation between 2-alkyl-3-hydroxynaphthalene-1,4-diones and nitroalkenes using a bifunctional thiourea catalyst, and a series of nitro-methanobenzo[7]annulenes with potential biological activities were synthesized in good yields with excellent enantio- and diastereoselectivities. A gram-scale synthesis and further transformation of the product demonstrated the synthetic value of this reaction.

Tuning the redox potential of Vitamin K3 derivatives by oxidative functionalization using a Ag(i)/GO catalyst

We propose herein initial results to develop optimum redox mediators by the combination of computational simulation and catalytic functionalization of the core structure of vitamin K3. We aim to correlate the calculated energy value of the LUMO

Organocatalytic Asymmetric Formal [3+2] Cycloaddition as a Versatile Platform to Access Methanobenzo[7]annulenes

Pharmaceutically and structurally important methanobenzo[7]annulenes were synthesized in very good yields with excellent enantio- and diastereoselectivities through an unprecedented organocatalytic formal [3+2] cycloaddition from readily available 2-alkyl-3-hydroxynaphthalene-1,4-diones and alkyl vinyl ketones.

Towards targeting anticancer drugs: Ruthenium(II)-arene complexes with biologically active naphthoquinone-derived ligand systems

Anticancer active metal complexes with biologically active ligands have the potential to interact with more than one biological target, which could help to overcome acquired and/or intrinsic resistance of tumors to small molecule drugs. In this paper we present the preparation of 2-hydroxy-[1,4]-naphthoquinone-derived ligands and their coordination to a RuII(η6-p-cymene)Cl moiety. The synthesis of oxime derivatives resulted in the surprising formation of nitroso-naphthalene complexes, as confirmed by X-ray diffraction analysis. The compounds were shown to be stable in aqueous solution but reacted with glutathione and ascorbic acid rather than undergoing reduction. One-electron reduction with pulse radiolysis revealed different behavior for the naphthoquinone and nitroso-naphthalene complexes, which was also observed in in vitro anticancer assays.

Design, synthesis, and biological testing of novel naphthoquinones as substrate-based inhibitors of the quinol/fumarate reductase from Wolinella succinogenes

Novel naphthoquinones were designed, synthesized, and tested as substrate-based inhibitors against the membrane-embedded protein quinol/fumarate reductase (QFR) from Wolinella succinogenes, a target closely related to QFRs from the human pathogens Helicobacter pylori and Campylobacter jejuni. For a better understanding of the hitherto structurally unexplored substrate binding pocket, a structure-activity relationship (SAR) study was carried out. Analogues of lawsone (2-hydroxy-1,4-naphthoquinone 3a) were synthesized that vary in length and size of the alkyl side chains (3b-k). A combined study on the prototropic tautomerism of 2-hydroxy-1,4-naphthoquinones series indicated that the 1,4-tautomer is the more stable and biologically relevant isomer and that the presence of the hydroxyl group is crucial for inhibition. Furthermore, 2-bromine-1,4-naphthoquinone (4a-c) and 2-methoxy-1,4-naphthoquinone (5a-b) series were also discovered as novel and potent inhibitors. Compounds 4a and 4b showed IC50 values in low micromolar range in the primary assay and no activity in the counter DT-diaphorase assay.

SINTESIS DE NAFTAZARINAS HIDROXILADAS

A variety of naphthazarines type 4 and 8 were prepared through Diels-Alder reactions of substituted 1,4-benzoquinones with 1,3-dienes.Thiele-Winter reaction of 5 afforded 6 which by chromic oxidation yielded naphthazarines 7 and/or naphthoquinones 9.Hydroxynaphthazarines of type 8 were synthesized from 5 through 2,3-epoxides of the type 14.The structural study of the products, by 1H-NMR, showed the typical tautomerism of the naphthazarine system.Palabras clave: hidroxinaftazarinas, reaccion Diels-Alder, reaccion Thiele-Winter

Naphthalene anti-psoriatic agents

Psoriasis in mammals is relieved by topically administering naphthalenes of the formula: STR1 wherein: R1 is alkoxy, alkylthio, optionally substituted phenoxy or optionally substituted phenylthio; R2 is hydrogen, lower alkyl, optionally substituted phenyl or optionally substituted phenylalkyl; R3 is lower alkyl, lower alkoxy, or halo and m is 0, 1 or 2, or R3 is optionally substituted phenyl, optionally substituted phenyl lower alkyl, optionally substituted phenyl lower alkoxy, amino, lower alkylamino, lower dialkylamino, cyano, or S(0)n R wherein R is lower alkyl; optionally substituted phenyl; optionally substituted phenyl lower alkyl; or optionally substituted heterocyclic aryl of three to nine ring atoms containing one or two heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and the pharmaceutically acceptable acid addition salts thereof; and m is 1 and n is 0, 1 or 2; and W is alkyl of one to seven carbon atoms, optionally substituted phenyl or optionally substituted benzyl.

Photochemistry of Epoxyquinone. 5. Photoinduced Cycloadditions of Epoxynaphthoquinone to Aldehydes, Ketones, and Oxygen

Irradation of a benzene solution of 2,3-dihydro-2,3-dimethyl-23-epoxy-1,4-naphthoquinone (3a) in the presence of aldehydes gives the primary 1,3-dioxolane adducts in good yields.Upon further irradation, the primary adducts undergo Photorearrangement to give alkylidenephthalides.A similar photocycloaddition reaction of 3a with aliphatic ketones was realized by their use as the reaction medium.When irradiated in the presence of oxygen in benzene, 3a was converted into 3-acetyl-3-acetoxyphthalide and 3-acetoxy-3-methylisochroman-1,4-dione presumably via the reaction ofsinglet oxygen with a carbonyl ylide, 4a.In contrast to 2,3-dialkylepoxynaphthoquinones 3a-d, the photoinduced cycloaddition of 2,3-dihydro-2,3-diphenyl-1,4-naphthoquinone (3e) to carbonyl compounds did not occur.The photoinduced cycloadditions of epoxynaphthoquinones to carbonyl compounds are believed to be HOMO-controlled reactions on the basis of substituent effects at the 2- and 3-positions of epoxynaphthoquinones and at the para position of the dipolarophiles, namely, aromatic aldehydes.