Sulforaphane homologues: Enantiodivergent synthesis of both enantiomers, activation of the Nrf2 transcription factor and selective cytotoxic activity

Abstract

2 HighlightsBoth enantiomers of sulforaphane and six homologues were obtained. The ability of the synthesized compounds to activate the Nrf2 is studied The cytotoxic activity of the analogues against cancer and healthy cells is reported.

Synthesis, evaluation, and metabolism of novel [6]-shogaol derivatives as potent Nrf2 activators

“…5,6 Therefore, Nrf2 is a potential target for many chronic diseases, such as chronic kidney disease, asthma, neurodegenerative diseases, and cancer. [7][8][9][10][11][12][13] It is known that small molecules Nrf2 activators, such as sulforaphane (SFN), 14 curcumin, 15 and chalcone derivatives, 16 have been identified as cancer chemopreventive agents. Screening for Nrf2 activators would lead to the discovery of new pharmaceuticals for oxidative stress-associated chronic diseases.…”

“…, or both(14), as well as their related derivatives(6-10 and 15-17). Our results clearly indicate that the departure of the ,-unsaturated carbonyl entity attenuated Nrf2-induced activities (Figure 1).…”

Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)

“…Besides their roles in plant defense, glucosinolates are thought to provide health benefits to humans owing to a variety of bioactivities of the isothiocyanates, for example, chemoprotective and antibacterial effects . The bioactivities are related to the reaction of isothiocyanates with biological nucleophiles such as amino‐ and sulfhydryl moieties of enzymes .…”

Organofluorine Isoselenocyanate Analogues of Sulforaphane: Synthesis and Anticancer Activity

“…Sulforaphane ( 1 ) is a naturally occurring isothiocyanate that is isolated from broccoli and other cruciferous vegetables . It has been a subject of intense investigations concerning its synthesis and the preparation of various analogues, as well as evaluation of the chemopreventive and anticancer properties. The anticancer activity of sulforaphane has been researched in many cancer cell lines, for example, breast, prostate, lung, colon, pancreas, and malignant melanoma.…”