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28.1.3 Product Subclass 3: Chalcogen-Substituted Benzo-1,4-quinones

DOI: 10.1055/sos-SD-028-00057

Kim, S. H.; Theodorakis, E. A.Science of Synthesis, (20062853.

General Introduction

This class of quinones includes compounds in which substitution at the periphery of the benzo-1,4-quinone framework is established via an oxygen and/or sulfur linkage. There is a lack of reported information on benzoquinones that are attached to other chalcogens, such as selenium or tellurium and even the sulfur-substituted benzo-1,4-quinones are rather rare and unexplored. Further information on this product subclass can be found in HoubenWeyl, Vol.7/3, pp599623. There are several reports of hydroxy- and alkoxy-substituted benzo-1,4-quinones, which, in fact, represent an important class of biologically active molecules. For example, ubiquinone-2 (1, R1=OH; n=2)[‌1‌] (Scheme 1) acts in bacteria and eukaryotes as an electron transporter during aerobic metabolism. In addition, the methylated and homologated analogue coenzyme Q10 (CoQ10) (1, R1=OMe; n=10)[‌2‌] is often referred to as the miracle nutrient, because it is involved in respiratory processes, cellular production of ATP, maintenance of heart-muscle strength and quenching of free radicals (Scheme 1). Moreover, maesanin (2),[‌3‌,‌4‌] a natural benzoquinone isolated from plants of the genus Myrsinaceae, has been found to elicit nonspecific immunostimulation and 5-lipoxygenase inhibition, while the marine sesquiterpene ilimaquinone (3) exhibits anti-HIV, antimitotic, and anti-inflammatory activities (Scheme 1).[‌5‌,‌6‌]

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References