Synthesis and antimicrobial activity of geminal bis-hydroperoxides

Tropina, V. I.; Krivykh, O. V.; Sadchikova, N. P.; Terent’ev, Alexander O.; Krylov, Igor B.

doi:10.1007/s11094-010-0441-6

Cited by 11 publications

(8 citation statements)

References 6 publications

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“…A geminal bis -hydroperoxides 239 synthesized from cyclic ketones 238 show pronounced in vitro antimicrobial and antifungal activity against B. cereus , E. coli , P. aeruginosa , S. aureus , C. albicans , and A. niger comparable with the effect of some antiseptics and, to a lesser extent, antibiotics ( Scheme 49 ) [ 217 ].…”

Section: Acyclic Peroxidesmentioning

confidence: 99%

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

et al. 2017

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The biological activity of organic peroxides is usually associated with the antimalarial properties of artemisinin and its derivatives. However, the analysis of published data indicates that organic peroxides exhibit a variety of biological activity, which is still being given insufficient attention. In the present review, we deal with natural, semi-synthetic and synthetic peroxides exhibiting anthelmintic, antiprotozoal, fungicidal, antiviral and other activities that have not been described in detail earlier. The review is mainly concerned with the development of methods for the synthesis of biologically active natural peroxides, as well as its isolation from natural sources and the modification of natural peroxides. In addition, much attention is paid to the substantially cheaper biologically active synthetic peroxides. The present review summarizes 217 publications mainly from 2000 onwards.

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Section: Acyclic Peroxidesmentioning

confidence: 99%

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

et al. 2017

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“…H 2 O 2 and iodine as a catalyst, geminal bishydroperoxides 239 were obtained from cyclic and acyclic ketones 238 in a yield of 50 to 98% (Scheme 88). All geminal bishydroperoxides 239 exhibit pronounced in vitro antimicrobial and antifungal activity against B. cereus, E. coli, P. aeruginosa, S. aureus, C. albicans, and A. niger [190]. However, the use of the pyridine/I2 system for unsaturated hydroperoxyacetal 236 did not provide the assembly of 1,2,4-trioxane 237.…”

Section: Iodine In the Synthesis Of Organic Peroxidesmentioning

confidence: 99%

“…This approach was also used in the synthesis of bishydroxyperoxides 241 from acetophenone and benzaldehydes 240. Unfortunately, peroxidation of compounds containing an electron-withdrawing substituent in the ring did not lead to the target geminal bishydroxyperoxides (Scheme 89) [190]. This approach was also used in the synthesis of bishydroxyperoxides 241 from acetophenone and benzaldehydes 240.…”

Section: Iodine In the Synthesis Of Organic Peroxidesmentioning

confidence: 99%

“…This approach was also used in the synthesis of bishydroxyperoxides 241 from acetophenone and benzaldehydes 240. Unfortunately, peroxidation of compounds containing an electron-withdrawing substituent in the ring did not lead to the target geminal bishydroxyperoxides (Scheme 89) [190]. The action of iodine as a Lewis acid is based on its interaction with the oxygen atom of the carbonyl group of 240, which facilitates the nucleophilic attack of hydrogen peroxide on the neighboring carbon atom.…”

Section: Iodine In the Synthesis Of Organic Peroxidesmentioning

confidence: 99%

“…The application of I 2 /H 2 O 2 and I 2 /TBHP systems to non-aromatic aldehydes allows one to obtain hydroxy-hydroperoxides 248 and tert-butylhydroxyperoxides 249 (Scheme 92) [190].…”

Section: Iodine In the Synthesis Of Organic Peroxidesmentioning

confidence: 99%

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Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides

et al. 2022

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Organic peroxides are an important class of compounds for organic synthesis, pharmacological chemistry, materials science, and the polymer industry. Here, for the first time, we summarize the main achievements in the synthesis of organic peroxides by the action of Lewis acids and heteropoly acids. This review consists of three parts: (1) metal-based Lewis acids in the synthesis of organic peroxides; (2) the synthesis of organic peroxides promoted by non-metal-based Lewis acids; and (3) the application of heteropoly acids in the synthesis of organic peroxides. The information covered in this review will be useful for specialists in the field of organic synthesis, reactions and processes of oxygen-containing compounds, catalysis, pharmaceuticals, and materials engineering.

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1,1‐Dihydroperoxides

Schwartz

Dussault

2014

Patai's Chemistry of Functional Groups

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Gem ‐dihydroperoxides ( g ‐DHPs), often referred to as 1,1‐dihydroperoxides, are a class of molecules of interest because of their reactivity as well as their utility as synthetic reagents and intermediates. This review begins with a listing of previous reviews and commercially available g ‐DHPs, followed by a brief discussion of safety and regulatory issues. The properties of g ‐DHPs are then overviewed, with an emphasis on the physical properties, biological activity, thermal stability, spectroscopic properties, and behavior on chromatographic media. The remaining sections describe the synthesis and reactions of g ‐DHPS. The largest of these sections describes the various methods for synthesis of g ‐DHPs based upon class of catalyst or reagent and compares applications of different reagents selected target skeletons. One of the most significant applications of g ‐DHPs, their use as precursors for 1,2,4,5‐tetraoxanes, is discussed in detail, including tabular comparisons of approaches to selected skeletons. The chapter concludes with a discussion of other important reactions of g ‐DHPs, including alkylations, nucleophilic and electrophile‐promoted additions to alkenes, acetalizations, acylations and acylation‐promoted fragmentations, acid‐promoted dimerizations and decompositions, silylations, and application as oxygen transfer agents.

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Synthesis and antimicrobial activity of geminal bis-hydroperoxides

Cited by 11 publications

References 6 publications

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions

Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides

1,1‐Dihydroperoxides

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