15254-76-9

Upstream product

• 67-56-1 methanol 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 18855-92-0 3-chlorojuglone 
• 52431-65-9 3-Bromojuglone 
• 69008-03-3 2-bromo-5-hydroxy-[1,4]naphthoquinone 
• 124-41-4 sodium methylate 
• 4923-57-3 2-chlorojuglone 
• 106697-17-0 2-Chloro-3-methoxyjuglone 
• 106697-18-1 2-Brom-5-hydroxy-3-methoxy-1,4-naphthochinon 
• 3905-27-9 4-(2',4',5'-trimethoxyphenyl)butanoic acid 
• 41067-05-4 2-(dimethylamino)-8-hydroxy-1,4-naphthalenedione 
• 4923-58-4 3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone 
• 74-88-4 methyl iodide 
• 54490-80-1 2-chloro-6-methoxy-p-benzoquinone 

Downstream Products

• 4923-58-4 3,5-dihydroxy-2,3-dihydro-1,4-naphthoquinone 
• 4923-55-1 2-Hydroxyjuglon 

Relevant academic research and scientific papers

Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity

To establish the structure-activity relationship of 5-hydroxy-1,4-naphthoquinones toward anticancer activity, a series of its derivatives were prepared and tested for the activity (IC50 in μM) against three cell lines; colo205 (colon adenocarcinoma), T47D (breast ductal carcinoma) and K562 (chronic myelogenous leukemia). Among them 2 (IC50: 2.3; 2.0; 1.4 μM), 6 (IC50: 1.9; 2.2; 1.3 μM), 9 (IC50: 0.7; 1.7; 0.9 μM) and 10 (IC50:1.7; 1.0; 1.2 μM) showed moderate to excellent activity. Our perception toward the DNA substitution of alkoxy groups at the C2 position of these naphthoquinones for the anticancer activity led us to investigate their reactivity of substitution toward dimethylamine as a nucleophile. The ease of the substitution of alkoxy groups at the C2 position with dimethylamine is strongly accelerated by hydroxyl group at C5 position and is well correlated with the found anticancer activity results.

Selective alkoxylation of 1,4-quinones

1, 4-Quinones have been alkoxylated selectively at the active quinonoid position using alkanols and alkenol in the presence of (a) Raney nickel, (b) silica gel and (c) Cubronze with iodine.

Method for dyeing keratinous fibres using a monohydroxyindole or dihydroxyindole and a non-oxidizing aromatic carbonyl derivative and dyeing agent

The present invention relates to a method for dyeing keratinous fibers, characterized in that the following are applied to the fibers: a) a composition (A) containing, in a medium appropriate for dyeing, at least one monohydroxyindole or dihydroxyindole, this application being preceded or followed by the application of b) a composition (B) containing, in a medium appropriate for dyeing, at least one aromatic carbonyl derivative chosen from hydroxyacetophenones, hydroxybenzophenones, 2-hydroxy-1,4-benzoquinones, hydroxy-1,4-naphthoquinones,amino-1,4-naphthoquinones,hydroxy-9,10-anthraquinones and amino-9,10-anthraquinones. It also relates to the dyeing agents for carrying it out.

Regiospecific Addition of Monooxygenated Dienes to Halo Quinones

In spite of their decreased polarity with respect to previously studied electron-rich analogues, monooxygenated dienes also react regiospecifically with halo quinones.The corresponding adducts can easily be aromatized on silica gel to isomeric polysubstituted naphthoquinones of unambiguous structure and therefore provide ready access to substrates for subsequent regiospecific annulations.The scope of this approach is illustrated by advantageous syntheses of several natural products: chimaphilin, 6-methylalizarin, 6-methylxantopurpurin, and barleriaquinone.The adductscan also give rise to a series of products in which the oxygen function of the dienes is preserved as a hydroxyl group in the quinone.To this end adducts derived from 1-oxygenated dienes and halo quinones were oxidized effectively with Jones reagent while those obtained from the 2-oxygenated isomers responded better to manganese dioxide.Relative positions of substituens in the adducts were readily confirmed by comparison of some of the hydroxylated oxidation products with known compounds of unambiguous structure.The method is again illustrated by the ready synthesis of a number of natural products including plumbagin, soranjidiol, isochrysophanol and its 8-methyl ether, and isozyganein and its 5-methyl ether.

Two New Syntheses of the Pyranojuglone Pigment α-Caryopterone

By a simple process, 3-methoxyjuglone ( = 8-hydroxy-2-methoxy-1,4-naphthoquinone; 9) has been synthesized from 1,2,4-trimethoxybenzene (5) and converted, after prenylation, to α-caryopterone (1; Scheme 1), a pyranojuglone pigment from Caryopteris clandonensis.On the other hand, juglone ( = 5-hydroxy-1,4-naphthoquinone; 12) was regioselectively prenylated at C(2) via its 1-methoxy-cyclohexa-1,3-diene adduct 15 (Scheme 2).The 2-prenyljuglone (4) thus formed led to 1 after oxidation and other reactions.