7473-18-9

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 64-17-5 ethanol 
• 60-29-7 diethyl ether 
• 36417-25-1 2-hydroxy-1,4-naphthoquinone silver salt 
• 75-03-6 ethyl iodide 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 574-00-5 1,2-Dihydroxynaphthalene 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 130-15-4 [1,4]naphthoquinone 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 87-66-1 2-hydroxyresorcinol 
• 3188-13-4 ethyl chloromethyl ether 
• 2066-93-5 3,4-dioxo-3,4-dihydro-naphthalene-1-sulfonic acid 

Downstream Products

• 59641-32-6 2-chloro-3-(ethoxy)-1,4-naphthoquinone 
• 6628-97-3 2-(phenylamino)naphthoquinone 
• 21720-68-3 2-(phenylamino)-4-(phenylimino)-1(4H)-naphthalenone 
• 94015-53-9 atovaquone 
• 57182-49-7 2-(p-toluidino)-1,4-naphthoquinone 

Relevant academic research and scientific papers

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

A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26

The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3?2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.

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.

Unusual, chemoselective etherification of 2-hydroxy-1,4-naphthoquinone derivatives utilizing alkoxymethyl chlorides: Scope, mechanism and application to the synthesis of biologically active natural product (±)-lantalucratin C

A novel etherification of 2-hydroxy-1,4-naphthoquinone derivatives with alkoxyalkyl chlorides and hydride bases is described. Precise study of the conditions and substrate scope suggested that the reaction occurs specifically in the molecule having a 2-hydroxy-1,4-benzoquinone skeleton. A chemoselective O-methylation reaction was achieved to afford a synthetically important intermediate, which offered easy access to a natural product possessing anti-tumor activity.

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

The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors

A series of 1,4-naphthoquinone derivatives diversely substituted at C-2, C-3, C-5 and C-8, prepared by reaction of amines, amino acids and alcohols with commercial 1,4-naphthoquinones, has been evaluated against papain and bovine spleen cathepsin B. These

Chemoselective reactions of 2,3-dichloro-1,4-naphthoquinone

The reaction of 2,3-dichloro-1,4-naphthoquinone with alkoxides, primary amines, and phenols was shown to proceed chemoselectively rather to the corresponding 2-substituted 3-chloro-naphthoquinones or 2,3-disubstituted quinones than to brazanquinone deriva

Microwave-induced Monohydroxymethylation and Monoalkoxylation of 1,4-Naphthoquinones

1,4-Naphthoquinones and its derivatives have been hydroxymethylated and alkoxylated in the quinone ring using, respectively, formalin or an alcohol, in the presence of K2CO3 or HgO by heating or microwave irradiation.

Microwave-induced Selective Alkoxylation of 1,4-Naphthoquinones

A new efficient alkoxylation of 1,4-naphthoquinones at the active quinonoid position is reported using alkanols and an alkenol in the presence of cerium chloride and iodine under microwave irradiation.

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.