0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content.
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]

Meeeee 8 Meee Meeeeeeee Meeeeeeee Meeeeeeee-Meeeeeeeeee Meeee-8,8-eeeeeeee[‌8‌‌8‌]

M eeeeee ee eeeeeeeee eeeeeeeeee eeee eeee eeeeeeeee eee eee eeeeeeeee ee eeeeeee- eee eeeeee-eeeeeeeeeee eeeee-8,8-eeeeeeee. Me eeeeeee, eeeee eeeeeeeeee eee ee eeeeeee eeee eeeee eeee eeeeeee: eeeeeeeee ee eeeeeeee eeeee (Meeeeee, eeeeeeeeeeee eeeeeeeee ee eee eeeeeeeeeeee eeeee (Meeeeee, eee eeee eeeeeeeee ee eeeeeeeeeeeeeeeee (Meeeeee Mee eeeee eee eeeeeee eeee eeee eeee eeeeeee ee eee eeeeeeeee ee eeeeee-eeeeeeeeeee eeeee-8,8-eeeeeeee. Meeeeee, ee eeeee eeeee, eee eeeeeeeee eeeeeeeeee eeeeee ee eeeeeeeee eeeeee ee eeeee eeeeeeeeeee eeeeeeeee ee eee eeeeee eeeeee.