Menadione: a platform and a target to valuable compounds synthesis

Abstract

Naphthoquinones are important natural or synthetic compounds belonging to the general class of quinones. Many compounds in this class have become drugs that are on the pharmaceutical market for the treatment of various diseases. A special naphthoquinone derivative is menadione, a synthetic naphthoquinone belonging to the vitamin K group. This compound can be synthesized by different methods and it has a broad range of biological and synthetic applications, which will be highlighted in this review.

KuQuinones: a ten years tale of the new pentacyclic quinoid compound

“…Quinone peculiar features are not limited to their interesting reversible electrochemical behaviour. Indeed, their skeleton can be easily modified 4–7 with the aim to tune their electronic and electrochemical properties, so extending the range of potential applications. Anthraquinones, naphthoquinones and benzoquinones have been used as electroactive compounds in energy storage devices, 8 as redox flow batteries, 9,10 lithium ions batteries, 8 supercapacitors, 11 in water-splitting processes, in hydrogen production, and in n-type Dye Sensitized Solar Cells (n-DSSCs).…”

Synthesis of thia-Michael-Type Adducts between Naphthoquinones and N-Acetyl-L-Cysteine and Their Biological Activity

“…Quinones are a class of organic compounds widely distributed in nature in animals, plants and microorganisms, where they are biosynthesized as secondary metabolites [ 1 ]. They can be chemically sub-divided into benzoquinones, naphthoquinones, and anthraquinones based on the carbocyclic aromatic ring of their corresponding reduced hydroquinonic form.…”

“…Naphthazarin (5,8-dihydroxynaphthalene-1,4-dione, often also indicated as 5,8-dihydroxy-1,4-naphthoquinone ( 5 ); Figure 2 ), a compound present in the Boraginaceae , Droseraceae , and Nepenthaceae families [ 25 , 26 ], has shown effects on oral squamous cell carcinoma [ 27 ], human breast cancer [ 28 ], human gastric cancer [ 29 ], and human colorectal cancer [ 30 ] cells. Menadione (2-methyl-1,4-naphthoquinone), also known as vitamin K 3 , is a synthetic compound used as a precursor in the synthesis of K 1 and K 2 vitamins and has showed to possess a wide range of biological activities, such as anticancer, antibacterial, antifungal, antimalarial, and anthelmintic activities [ 1 ].…”

Organophotoredox-catalyzed cyanoalkylation of 1,4-quinones

“…1) display potent biological activities. 2 Considering the importance of alkylated quinones, many strategies have been developed for the incorporation of alkyl chains into quinones. 3 Furthermore, alkylnitriles are organic skeletons that can be found in many drugs and natural products.…”