Chemical modifications of imidazole-containing alkoxyamines increase C–ON bond homolysis rate: Effects on their cytotoxic properties in glioblastoma cells

Alkoxyamines Designed as Potential Drugs against Plasmodium and Schistosoma Parasites

“…Among more than a hundred of prepared alkoxyamines (see Figure S1 ), the derivatives whose synthesis, reactivity and biological activity will be discussed in detail are depicted in Figure 2 . Most of the alkoxyamines were prepared as previously reported [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ]. The syntheses of new compounds are depicted in Scheme 1 (compound 6F ), Scheme 2 (compound 2F and 4F ), and Scheme 3 (compound 8F ).…”

“…LC-MS: t R [( RR / SS )- 2F or ( RS/SR )- 2F ] = 13.4 min, m/z = 571.3 (M + H + ); t R [ 22 ] = 4.7 min, m/z = 262.3 (M + H + ), 284.3 (M + Na + ); t R [ 24 ] = 8.0 and 10.0 min, m/z = 521.4 (M + H + ), 543.4 (M + Na + ); t R [ 25 ] = 5.8 min, m/z = 276.3 (M + H + ), 298.3 (M + Na + ).…”

Homolysis/mesolysis of alkoxyamines activated by chemical oxidation and photochemical-triggered radical reactions at room temperature

“…Such alkoxyamines have interesting properties for potential applications in industry, e.g., safe storage of initiators for radical polymerizations, 5,12 or in biology, e.g., drugs for cancer or parasites. 10,11,[13][14][15][16][17][18] While the focus of these studies has been on triggering alkoxyamine homolysis, to form a nitroxide and carbon-centred radical, recently it has been shown that upon oxidation, through electrochemical [19][20][21][22][23] or photoredox 24,25 methods, alkoxyamines can spontaneously undergo mesolytic cleavage instead. Depending on the leaving group and other species present, this process can yield nitroxides and carbocations, or alternatively oxoamoniums and carbon-centred radicals.…”

An enzymatic acetal/hemiacetal conversion for the physiological temperature activation of the alkoxyamine C–ON bond homolysis

“…[24][25][26] For a few years, 27 our groups have promoted the therapeutic application of alkoxyamines as drugs against cancer. [28][29][30] For such an application, we aim to combine four antagonistic features: a highly stable precursor (or pro-drug), a highly reactive drug, random reactivity, and specific addressing. The aim is to circumvent drugresistant cancer by using highly reactive and unselective drugs, and to improve the patient welfare by using highly selective pro-drugs via specific addressing, which is a step towards personalized medicine.…”