ChemInform Abstract: Reductive Activation of Arenes. Part 9. Reaction of the Two-Electron Reduction Products of Benzonitrile and 1-Naphthonitrile with Alkyl Halides in Liquid Ammonia.

ChemInform ◽  
2010 ◽  
Vol 26 (34) ◽  
pp. no-no
Author(s):  
I. I. BIL'KIS ◽  
T. A. VAGANOVA ◽  
V. D. SHTEINGARTS
Keyword(s):  
Liquid Ammonia ◽  
Alkyl Halides ◽  
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

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

Reactions of aliphatic halides with solutions of alkali metals in liquid ammonia: I. Experiments with alkyl halides

2010 ◽  
Vol 81 (12) ◽  
pp. 1033-1052 ◽  
Author(s):  
A. Beverloo ◽  
M. C. Dieleman ◽  
P. E. Verkade ◽  
K. S. de Vries ◽  
B. M. Wepster
Keyword(s):  
Alkali Metals ◽  
Liquid Ammonia ◽  
Alkyl Halides

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.

Electrochemical properties and catalytic reactivity of cobalt complexes with redox-active meso-substituted porphycene ligands

2020 ◽  
Vol 24 (01n03) ◽  
pp. 90-97 ◽  
Author(s):  
Taro Koide ◽  
Zihan Zhou ◽  
Ning Xu ◽  
Yoshio Yano ◽  
Toshikazu Ono ◽  
...  
Keyword(s):  
Reduction Potential ◽  
Energy Levels ◽  
Cobalt Complexes ◽  
Alkyl Halides ◽  
Reduction Potentials ◽  
Positive Side ◽  
Redox Active ◽  
Catalytic Reactivity ◽  
Electron Reduction ◽  
The One

The cobalt complexes of meso-aryl substituted porphycenes were synthesized and characterized. The reduction potentials of the complexes were shifted to the positive side depending on the strength of the electron-withdrawing properties of the meso-substituents, while the optical properties, such as the absorption spectra of these complexes, were similar. This suggests that the energy levels of the molecular orbitals of the complexes were changed by the meso-substituents while the gaps of the orbitals were not significantly changed. The one-electron reduction of the complex did not afford the Co(I) species, but the ligand-reduced radical anion, which was characterized by electrospectrochemistry. The generated ligand-reduced species reacted with alkyl halides to form the Co(III)-alkyl complex. As a result, the reduction potential of the electrolytic reaction could be directly controlled by the substituents of the porphycene. The catalytic reaction with trichloromethylbenzene was also performed and it was found that the ratio of the obtained products was changed by the reduction potentials of the catalyst, [Formula: see text]. the cobalt porphycenes.

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