Synthesis and Notable Antimalarial Activity of Acyclic Peroxides, 1-(Alkyldioxy)-1-(methyldioxy)cyclododecanes

Hamada, Yoshiaki; Tokuhara, Hidekazu; Masuyama, Araki; Nojima, Màsatomo; Kim, Hye Sook; Ono, Kanako; Ogura, Naoto; Wataya, Yusuke

doi:10.1021/jm010473w

Cited by 69 publications

(39 citation statements)

References 15 publications

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“…Synthesis of gem-dihydroperoxides is reported in the literature and these are formed by reacting keto compounds with aqueous hydrogen peroxide [21]. Dihydroperoxides may serve as intermediates for the synthesis of acyclic peroxides with anti-malarial activity [22].…”

Section: Proton Position a Pentoxifyllinementioning

confidence: 99%

Degradation studies of pentoxifylline: Isolation and characterization of a novel gem-dihydroperoxide derivative as major oxidative degradation product

Mone¹,

Chandrasekhar²

2010

Journal of Pharmaceutical and Biomedical Analysis

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Section: Proton Position a Pentoxifyllinementioning

confidence: 99%

Degradation studies of pentoxifylline: Isolation and characterization of a novel gem-dihydroperoxide derivative as major oxidative degradation product

Mone¹,

Chandrasekhar²

2010

Journal of Pharmaceutical and Biomedical Analysis

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“…In addition, more 1, 2, 4, 5-tetraoxepanes, 1, 2, 4, 5-tetraoxocanes, and spiro-1, 2, 4, 5-tetraoxacycloalkanes ( Figure 39) were synthesized by Japanese researchers [293][294][295][296]. 1, 2, 4, 5, 7-Pentaoxocanes with alkyl and aryl substituents were also synthesized ( Figure 39).…”

Section: Dimers and Trimersmentioning

confidence: 99%

A golden phoenix arising from the herbal nest — A review and reflection on the study of antimalarial drug Qinghaosu

Liu

2010

Front. Chem. China

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Qinghaosu (QHS) and its derivatives are a new generation of antimalarial drugs characterized by fast action, high efficacy, and good tolerance. This feature article states the discovery of QHS from traditional Chinese medicine qinghao (Artemisia annua L.) and reviews the progress during the past four decades in the research of phytochemistry of A. annua, chemical reactions and biotransformation of QHS, chemical synthesis and biosynthesis of QHS, synthesis and antimalarial activity of QHS derivatives and analogs, pharmacological studies, clinical application, and the antimalarial mechanism. Undoubtedly, QHS is an example of the value of traditional Chinese medicine in modern medicinal research.

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“…Also, these compounds are important intermediates in synthesis of a number of classes of peroxides including tetraoxanes [4][5][6], silateraoxans [7], spirobisperoxyketals [8,9], bisperoxyketals [10], and 1,2,4,5-tetraoxacycloalkanes [11,12]. Gem-dihydroperoxides have also been employed as initiators for radical polymerization reactions [13], as precursors for synthesis of dicarboxylic acid esters [14], and as reagents for oxidation reactions such epoxidation of α,β-unsaturated ketones [15,16], enantioselective oxidation of 2-substituted 1,4-naphtoquinones [17], oxidation of sulfides [18,19], and as suitable oxidants in other synthetic organic reactions [15,20,21].…”

Section: Introductionmentioning

confidence: 99%

Sulfamic acid: as a green and reusable homogeneous catalyst for peroxidation of ketones and aldehydes using aqueous 30 % H2O2

et al. 2015

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22, 23], (ii) reaction of ketals with H 2 O 2 in the presence of tungstic acid [24], or BF 3 ·Et 2 O [25], and (iv) peroxidation of ketones using an acidic solvent [26]. However, many of these methods have certain drawbacks including use of concentrated H 2 O 2 and excess acid, low yield, limited substrate range and production of mixtures of peroxidic products [27]. Also, poor selectivity and the presence of ozonesensitive groups in the substrates are further limitations in ozonolysis reaction. To avoid such limitations, recently, reactions of ketones and aldehydes with H 2 O 2 in the presence of Lewis acids in organic solvents have been reported. Among the Lewis acids, I 2 [28, 29], ceric ammonium nitrate (CAN) [30], CSA [31], NaHSO 4 ·SiO 2 [32], Re 2 O 7 [33], and PMA [34] have been reported as the catalysts in the synthesis of gem-dihydroperoxides with aqueous H 2 O 2 .In continuation of our efforts to explore new catalysts for synthesis of gem-dihydroperoxides [35,36]. Herein, we wish to introduce the sulfamic acid as a low-cost, green and effective recoverable solid catalyst in the synthesis of gemdihydroperoxides from ketones and aldehydes with 30 % aqueous H 2 O 2 at room temperature (Scheme 1).Sulfamic acid (SA) (NH 2 SO 3 H) is commercially available green heterogeneous catalyst that is solvable in water and has been used widely as an effective catalyst in organic synthesis [37,38]. ExperimentalSolvents, reagents, and chemical materials were obtained from Aldrich and Merck chemical companies and purified prior to use. Nuclear magnetic resonance spectra were recorded on JEOL FX 90Q using tetramethylsilane (TMS) as an internal standard. Infrared spectra were recorded on a PerkinElmer GX FT IR spectrometer (KBr pellets).Abstract Sulfamic acid has been used as an active, lowcost and reusable solid catalyst for conversion of ketones and aldehydes to corresponding gem-dihydroperoxides using 30 % aqueous hydrogen peroxide at room temperature. The reactions proceed with high rates and excellent yields.

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Synthesis and Notable Antimalarial Activity of Acyclic Peroxides, 1-(Alkyldioxy)-1-(methyldioxy)cyclododecanes

Abstract: Of several bis(alkyldioxy)alkanes and the related acyclic peroxides prepared in this study, 1,1-bis(methyldioxy)cyclododecane showed the most notable antimalarial activity particularly in vivo (almost a half of that of artemisinin).

Cited by 69 publications

References 15 publications

Degradation studies of pentoxifylline: Isolation and characterization of a novel gem-dihydroperoxide derivative as major oxidative degradation product

Degradation studies of pentoxifylline: Isolation and characterization of a novel gem-dihydroperoxide derivative as major oxidative degradation product

A golden phoenix arising from the herbal nest — A review and reflection on the study of antimalarial drug Qinghaosu

Sulfamic acid: as a green and reusable homogeneous catalyst for peroxidation of ketones and aldehydes using aqueous 30 % H2O2

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