Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of tert-butyl hydroperoxide as both an oxidant and a methylene source

2018 ◽  
Vol 16 (44) ◽  
pp. 8620-8628 ◽  
Author(s):  
Om P. S. Patel ◽  
Nitesh Kumar Nandwana ◽  
Ajay Kumar Sah ◽  
Anil Kumar
Keyword(s):  
Carbon Source ◽  
Dual Role ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide

A metal-free method is developed for the aminomethylation of imidazoheterocycles with 2/4-aminoheterocycles using TBHP as a carbon source as well as an oxidant.

The Fe(III)-catalyzed functionalization of saturated hydrocarbons by tert-butyl hydroperoxide: Mechanistic studies on the role of dioxygen

1992 ◽  
Vol 33 (38) ◽  
pp. 5473-5476 ◽  
Author(s):  
Derek H.R. Barton ◽  
Stéphane D. Bévière ◽  
Warinthorn Chavasiri ◽  
Darío Doller ◽  
Bin Hu
Keyword(s):  
Mechanistic Studies ◽  
Saturated Hydrocarbons ◽  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide

Glutathione protects against exogenous oxidant injury to rabbit renal proximal tubules

1988 ◽  
Vol 255 (5) ◽  
pp. F874-F884
Author(s):  
J. M. Messana ◽  
D. A. Cieslinski ◽  
R. P. O'Connor ◽  
H. D. Humes
Keyword(s):  
Oxidant Stress ◽  
Glutathione Depletion ◽  
Plasma Membrane Permeability ◽  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
Cation Homeostasis ◽  
Tert Butyl Hydroperoxide ◽  
Organ Systems ◽  
Nonprotein Thiols

Glutathione, comprising a major portion of cellular nonprotein thiols, plays a central role in a diverse group of cell metabolic functions. Glutathione and related enzyme systems have been shown to protect against both toxin and oxidant-induced injury in several organ systems. The role of glutathione in protecting renal epithelia against oxidant stress has not been investigated previously. We report here the response of enriched, isolated rabbit renal proximal tubule segments to oxidant stress induced by tert-butyl hydroperoxide. In addition, the effects of glutathione depletion by various biochemical means and of exogenous glutathione supplementation on the response of tubule segments to tert-butyl hydroperoxide exposure are described. Depletion of cell glutathione by several distinct methods potentiates oxidant-induced injury. Augmentation of cellular glutathione affords significant protection against exogenous oxidant stress. The protective effect of glutathione may reside in its ability, in conjunction with glutathione peroxidase, to arrest the propagation of lipid peroxidation and, therefore, to minimize alterations in plasma membrane permeability. The results of this study do not exclude the possibility that glutathione prevents tert-butyl hydroperoxide induced oxidation of critical sulfhydryl groups of catalytic or structural proteins associated with control of cell cation homeostasis. These results confirm the important role of glutathione in protecting renal tubular epithelia against oxidant stress.

scholarly journals tert-Butyl Hydroperoxide (tBHP)-Induced Lipid Peroxidation and Embryonic Defects Resemble Glucose-6-Phosphate Dehydrogenase (G6PD) Deficiency in C. elegans

2020 ◽  
Vol 21 (22) ◽  
pp. 8688
Author(s):  
Hung-Chi Yang ◽  
Hsiang Yu ◽  
Tian-Hsiang Ma ◽  
Wen-Ye Tjong ◽  
Arnold Stern ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
G6pd Deficiency ◽  
Short Term ◽  
Butyl Hydroperoxide ◽  
Tert Butyl ◽  
C Elegans ◽  
Tert Butyl Hydroperoxide ◽  
Calcium Independent Phospholipase A2 ◽  
Glucose 6 Phosphate Dehydrogenase

G6PD is required for embryonic development in animals, as severe G6PD deficiency is lethal to mice, zebrafish and nematode. Lipid peroxidation is linked to membrane-associated embryonic defects in Caenorhabditis elegans (C. elegans). However, the direct link between lipid peroxidation and embryonic lethality has not been established. The aim of this study was to delineate the role of lipid peroxidation in gspd-1-knockdown (ortholog of g6pd) C. elegans during reproduction. tert-butyl hydroperoxide (tBHP) was used as an exogenous inducer. Short-term tBHP administration reduced brood size and enhanced germ cell death in C. elegans. The altered phenotypes caused by tBHP resembled GSPD-1 deficiency in C. elegans. Mechanistically, tBHP-induced malondialdehyde (MDA) production and stimulated calcium-independent phospholipase A2 (iPLA) activity, leading to disturbed oogenesis and embryogenesis. The current study provides strong evidence to support the notion that enhanced lipid peroxidation in G6PD deficiency promotes death of germ cells and impairs embryogenesis in C. elegans.

ChemInform Abstract: Metal-Free Csp3-N Bond Cleavage of Amides Using tert-Butyl Hydroperoxide as Oxidant.

ChemInform ◽  
2015 ◽  
Vol 46 (28) ◽  
pp. no-no ◽  
Author(s):  
Shengmei Guo ◽  
Zheng Zhu ◽  
Lin Lu ◽  
Wenbiao Zhang ◽  
Jiuhan Gong ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide

scholarly journals α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones

2017 ◽  
Vol 13 ◽  
pp. 1079-1084 ◽  
Author(s):  
Liquan Tan ◽  
Cui Chen ◽  
Weibing Liu
Keyword(s):  
Oxidative Coupling ◽  
Optimum Conditions ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Radical Intermediates ◽  
Tert Butyl Hydroperoxide ◽  
Aryl Ketones

We present a metal-free method for α-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I2−tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products in moderate to excellent yields. A series of control experiments were performed; the results suggest the involvement of radical pathways. Multiple radical intermediates were generated in situ and the overall process involved several different reactions, which proceeded self-sequentially in a single reactor. A labeling experiment using 18O-labeled H2O confirmed that the oxygen in the product was derived from TBHP, not from H2O in the TBHP solvent.

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