ChemInform Abstract: Reductive Activation of Arenes. Part 7. Alkylation of 9- Cyanoanthracene Two-Electron Reduction Products in Liquid Ammonia.

ChemInform ◽  
2010 ◽  
Vol 26 (3) ◽  
pp. no-no
Author(s):  
T. A. VAGANOVA ◽  
E. V. PANTELEEVA ◽  
A. P. TANANAKIN ◽  
V. D. SHTEINGARTS ◽  
I. I. BILKIS
Keyword(s):  
Liquid Ammonia ◽  
Reductive Activation ◽  
Electron Reduction

Reductive activation of arenes. VII. Alkylation of 9-cyanoanthracene two-electron reduction products in liquid ammonia.

Tetrahedron ◽  
1994 ◽  
Vol 50 (33) ◽  
pp. 10011-10020 ◽  
Author(s):  
Tamara A. Vaganova ◽  
Elena V. Panteleeva ◽  
Andrej P. Tananakin ◽  
Vitalij D. Shteingarts ◽  
Itzhak I. Bilkis
Keyword(s):  
Liquid Ammonia ◽  
Reductive Activation ◽  
Electron Reduction

scholarly journals Enzymatic single-electron reduction and aerobic cytotoxicity of tirapazamine and its 1-oxide and nor-oxide metabolites

Chemija ◽  
2018 ◽  
Vol 29 (4) ◽  
Author(s):  
Jonas Šarlauskas ◽  
Aušra Nemeikaitė-Čėnienė ◽  
Audronė Marozienė ◽  
Lina Misevičienė ◽  
Mindaugas Lesanavičius ◽  
...  
Keyword(s):  
Side Effects ◽  
Anticancer Agent ◽  
Redox Cycling ◽  
Nitroaromatic Compounds ◽  
Single Electron ◽  
Reductive Activation ◽  
Cell Nuclei ◽  
Electron Reduction ◽  
Phenylene Diamine

Aerobic cytotoxicity of 3-amino-1,2,4-benzotriazine-1,4-dioxide (tirapazamine, TPZ), a bioreductively activated hypoxia-specific anticancer agent, is responsible for TPZ side effects in chemotherapy. In order to clarify its mechanisms, we examined the aerobic cytotoxicity of TPZ and its main metabolites, 3-amino-1,2,4-benzotriazine-1-oxide and 3-amino-1,2,4-benzotriazine in murine hepatoma MH22a cells, and their reduction by NADPH:cytochrome P-450 reductase (P-450R) and ferredoxin:NADP+ reductase (FNR). Analogous studies of several quinones and nitroaromatic compounds with similar values of single-electron reduction midpoint potentials (E17) were carried out. In single-electron reduction by P-450R and FNR, the reactivity of TPZ and its monoxide was similar to that of quinones and nitroaromatics, and increased with an increase in their E17. The cytotoxicity of TPZ and its metabolites possessed a prooxidant character, because it was partly prevented by an antioxidant N,N’-diphenyl-p-phenylene diamine and desferrioxamine, and potentiated by 1,3-bis(2-chloroethyl)-1-nitrosourea. Importantly, the cytotoxicity of TPZ and, possibly, its 1-N-oxide, was much higher than that of quinones and nitroaromatics with similar values of E17 and redox cycling activities. A possible additional factor in the aerobic cytotoxicity of TPZ is its reductive activation in oxygen-poor cell nuclei, leading to the formation of DNA-damaging species similar to those forming under hypoxia.

scholarly journals Reverse Polarity Reductive Functionalization of Tertiary Amides via a Dual Iridium Catalyzed Hydrosilylation & SET Strategy

2020 ◽  
Author(s):  
Tatiana Rogova ◽  
Pablo Gabriel ◽  
Stamatia Zavitsanou ◽  
Jamie Leitch ◽  
Fernanda Duarte ◽  
...  
Keyword(s):  
Active Pharmaceutical Ingredient ◽  
Building Blocks ◽  
Chemical System ◽  
Secondary Amide ◽  
Reductive Activation ◽  
Tertiary Amide ◽  
New Strategy ◽  
Tandem Process ◽  
Electron Reduction ◽  
Tertiary Amides

A new strategy for the mild generation of synthetically valuable α-amino radicals from robust tertiary amide building blocks has been developed. By combining Vaska’s complex-catalyzed tertiary amide reductive activation and photochemical single electron reduction into a streamlined tandem process, metastable hemiaminal intermediates were successfully transformed into nucleophilic α-amino free radical species. This umpolung approach to such reactive intermediates was exemplified through coupling with an electrophilic dehydroalanine acceptor, resulting in the synthesis of an array of α-functionalized tertiary amine derivatives, previously inaccessible from the amide starting materials. The utility of the strategy was expanded to include secondary amide substrates, intramolecular variants and late stage functionalization of an active pharmaceutical ingredient. DFT analyses were used to establish the reaction mechanism and elements of the chemical system that were responsible for the reaction’s efficiency.

Anionic products of the two-electron reduction of aromatic nitriles in liquid ammonia

1994 ◽  
Vol 7 (3) ◽  
pp. 153-161 ◽  
Author(s):  
Isaak I. Bilkis ◽  
Tamara A. Vaganova ◽  
Elena V. Panteleeva ◽  
Georgij E. Salnikov ◽  
Andrej P. Tananakin ◽  
...  
Keyword(s):  
Liquid Ammonia ◽  
Aromatic Nitriles ◽  
Electron Reduction
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