New Amino Endoperoxides Belonging to the Antimalarial G‐Factor Series

Givelet, Cécile; Bernat, Virginie; Mathieu, Daniel; André-Barrès, Christiane; Vial, Henri

doi:10.1002/ejoc.200700086

Cited by 13 publications

(3 citation statements)

References 19 publications

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“…Compounds with high antimalarial [ 11 – 23 ], antihelminthic [ 24 – 28 ], and antitumor activities [ 29 – 34 ] were found among natural, semisynthetic, and synthetic peroxides. The main biologically active frame of these compounds includes five-membered 1,2-dioxolane [ 35 – 37 ], 1,2,4-trioxolane [ 38 – 39 ], and six-membered 1,2-dioxane [ 40 – 42 ], 1,2-dioxene [ 43 ], 1,2,4-trioxane [ 22 , 44 – 45 ] cycles. The naturally occuring peroxide artemisinin and its semisynthetic derivatives, artemether, arteether, and artesunate, are applied in large scale for malaria treatment [ 46 – 47 ].…”

Section: Introductionmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

183

136

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SummaryThis review is the first to collate and summarize main data on named and unnamed rearrangement reactions of peroxides. It should be noted, that in the chemistry of peroxides two types of processes are considered under the term rearrangements. These are conventional rearrangements occurring with the retention of the molecular weight and transformations of one of the peroxide moieties after O–O-bond cleavage. Detailed information about the Baeyer−Villiger, Criegee, Hock, Kornblum−DeLaMare, Dakin, Elbs, Schenck, Smith, Wieland, and Story reactions is given. Unnamed rearrangements of organic peroxides and related processes are also analyzed. The rearrangements and related processes of important natural and synthetic peroxides are discussed separately.

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Section: Introductionmentioning

confidence: 99%

Rearrangements of organic peroxides and related processes

Yaremenko¹,

Vil²,

Demchuk³

et al. 2016

Beilstein J. Org. Chem.

183

136

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“…The use of aldehydes (R 1 R 2 CHCHO) with R 1 or R 2 bearing a hydroxyl group (R 1 or R 2 equals to CH 2 OH or CH 2 CH 2 OH, and CH 3 ) allows the obtention of endoperoxides with a functionalized lateral chain which are presented in Table 2 together with their antiplasmodial activities. In all cases, this hydroxyl group was protected as a tert-butyldiphenyl silyl (TBDPS) [51,61] or a paramethoxybenzyl (PMB) group. [62] Methylation of the peroxyhemiketal moiety, cleavage of the protective group, and terminal hydroxyl transformation afforded mono and difluoro-endoperoxides 25, 26 with interesting antiplasmodial activities (lower than 1 .…”

Section: Modifications On the Lateral Chainmentioning

confidence: 99%

Antimalarial Bicyclic Peroxides Belonging to the G-Factor Family: Mechanistic Aspects of their Formation and Iron (II) Induced Reduction

Ruiz¹,

Azéma²,

Payrastre³

et al. 2014

CTMC

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Artemisinin and its derivatives are peroxide-containing compounds targeting P. falciparum. We review here structural analogues of bicyclic peroxides belonging to the G factors family presenting antimalarial properties. They were synthesised under Mannich type conditions, followed by an autoxidation step resulting exclusively in the peroxide. As the electron transfer from haem or free iron to the peroxide is the first step in the mode of action of artemisinin-like compounds, the redox properties of some endoperoxides were studied by electrochemistry allowing the evaluation of the reduction standard potentials. The Fe(II) induced reduction was also investigated and the reactivity of the C-centered radical intermediate formed was linked to the antimalarial activity. These bicyclic peroxides both with various hybrid molecules containing the endoperoxide framework were evaluated in vitro against Plasmodium falciparum. They exhibited moderate to good activities.

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“…In the course of the large-scale search for synthetically accessible and cheap antimalarial peroxides (compared with natural and semi-synthetic structures), it was found that structures containing 1,2-dioxolane [ 88 – 90 ], 1,2,4-trioxolane [ 91 – 101 ], 1,2-dioxane [ 102 – 112 ], 1,2-dioxene [ 113 – 119 ], 1,2,4-trioxane [ 120 – 127 ] or 1,2,4,5-tetraoxane rings [ 128 – 146 ] exhibit pronounced activity, and in some cases, even superior to that of artemisinin.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

Terent’ev¹,

Borisov²,

Vil³

et al. 2014

Beilstein J. Org. Chem.

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SummaryThe present review describes the current status of synthetic five and six-membered cyclic peroxides such as 1,2-dioxolanes, 1,2,4-trioxolanes (ozonides), 1,2-dioxanes, 1,2-dioxenes, 1,2,4-trioxanes, and 1,2,4,5-tetraoxanes. The literature from 2000 onwards is surveyed to provide an update on synthesis of cyclic peroxides. The indicated period of time is, on the whole, characterized by the development of new efficient and scale-up methods for the preparation of these cyclic compounds. It was shown that cyclic peroxides remain unchanged throughout the course of a wide range of fundamental organic reactions. Due to these properties, the molecular structures can be greatly modified to give peroxide ring-retaining products. The chemistry of cyclic peroxides has attracted considerable attention, because these compounds are used in medicine for the design of antimalarial, antihelminthic, and antitumor agents.

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New Amino Endoperoxides Belonging to the Antimalarial G‐Factor Series

Cited by 13 publications

References 19 publications

Rearrangements of organic peroxides and related processes

Rearrangements of organic peroxides and related processes

Antimalarial Bicyclic Peroxides Belonging to the G-Factor Family: Mechanistic Aspects of their Formation and Iron (II) Induced Reduction

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

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