Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: direct evidence for nucleophilic O-1,2-aryl shifts

Kamata, Masaki; Ohta, Motoko; Komatsu, Ken Ichi; Kim, Hye Sook; Wataya, Yusuke

doi:10.1016/s0040-4039(02)00166-1

Cited by 21 publications

(12 citation statements)

References 23 publications

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“…Under these conditions, the yield of endoperoxide 134b for diphenyl-substituted all-carbon-tethered substrate 132b (n = 0) is very poor, but it can be improved to 48% by addition of Mg(ClO 4 ) 2 134 . A similar positive effect of Mg(ClO 4 ) 2 on photooxygenation of electronpoor 2,6-diaryl-1,6-heptadienes of type 132 (Ar = Ph or p-FC 6 H 4 , n = 1) was reported 138 . Additional increase in the yields of bicyclic peroxides of type 134 has been achieved by replacing the sensitizer DCA with a stronger oxidizing agent like 2,4,6-triphenylpyrylium tetrafluoroborate 138 .…”

Section: Scheme 30supporting

confidence: 74%

“…A similar positive effect of Mg(ClO 4 ) 2 on photooxygenation of electronpoor 2,6-diaryl-1,6-heptadienes of type 132 (Ar = Ph or p-FC 6 H 4 , n = 1) was reported 138 . Additional increase in the yields of bicyclic peroxides of type 134 has been achieved by replacing the sensitizer DCA with a stronger oxidizing agent like 2,4,6-triphenylpyrylium tetrafluoroborate 138 . Elongation of the carbon tether between the two styryl units in substrates 132 (n > 2) significantly reduces the yield of endoperoxides 134.…”

Section: Scheme 30supporting

confidence: 74%

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Synthesis of Cyclic Peroxides

Korshin

Bachi

2009

Patai's Chemistry of Functional Groups

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Section: Scheme 30supporting

confidence: 74%

Section: Scheme 30supporting

confidence: 74%

Synthesis of Cyclic Peroxides

Korshin

Bachi

2009

Patai's Chemistry of Functional Groups

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“…4). Upon 4 þ 2 cycloaddition with photogenerated singlet oxygen, the precursor 1,6-dienes, easily obtained from symmetrical diaryldiketones and 1,4-diaryl-cyclohexadienes, afforded, after reduction with diimide, 9 and 10, respectively, Kamata et al 43 reported an improved synthesis of endoperoxides 9 by using 2,4,6-triphenylpyrylium tetrafluoroborate (TPPBF 4 )-induced photo-electron transfer (PET) oxygenation. p-Methoxy-substituted 9a, and p-fluoro-substituted 10, only 10-fold less potent than 1, were the best of their respective classes.…”

Section: S a T U R A T E D 1 -D I O X A N E S ( E N D O P E R O Xmentioning

confidence: 99%

“…p-Methoxy-substituted 9a, and p-fluoro-substituted 10, only 10-fold less potent than 1, were the best of their respective classes. [44][45][46] Kamata et al 43 noted that the p-fluoro derivative of 9a was equipotent to the unsubstituted prototype bicyclo[3.2.2]nonane. However, Posner et al 46 reported that the p-fluoro derivative was more potent than its unsubstituted prototype bicyclo[2.2.2]octane.…”

Section: S a T U R A T E D 1 -D I O X A N E S ( E N D O P E R O Xmentioning

confidence: 99%

Synthetic peroxides as antimalarials

Tang

Dong²,

Vennerstrom³

2004

Medicinal Research Reviews

255

123

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The discovery of artemisinin in 1971 initiated a new era in antimalarial chemotherapy. Although the clinically useful semisynthetic artemisinin derivatives are rapid acting and potent antimalarial drugs, they have short half-lives and must be administered over a period of 5-7 days, leading to noncompliance and recrudescence. With this in view, many synthetic antimalarial peroxides have been prepared. Yet, identification of orally active synthetic peroxide drug development candidates that are easily synthesized, inexpensive, and with good biopharmaceutical properties has been surprisingly difficult. In this review, we document the pitfalls and progress made in this endeavor. For each of 15 synthetic peroxide structural classes, we note highlights of the synthetic routes, product stereochemistry, and origin of the peroxide O atoms. Both in vitro and in vivo antimalarial data are then discussed and any SAR noted. Available data indicates that several synthetic 1,2,4-trioxanes are only marginally less effective than the semisynthetic artemisinins. Within a given peroxide chemical family, the more lipophilic members are more potent and possess better oral antimalarial activity in animal models than their more polar counterparts. This poses a challenge to identify peroxide structures with suitable "drug-like" physicochemical properties. Nonetheless, substantial progress has been made in the identification of a new generation of synthetic antimalarial peroxides.

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“…2,4,6-Triphenylpyrylium tetrafluoroborate was used as the sensitizer for singlet oxygen generation (Scheme 54) [301]. …”

Section: Reviewmentioning

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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Synthesis, Fe(II)-induced degradation, and antimalarial activities of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonanes: direct evidence for nucleophilic O-1,2-aryl shifts

Cited by 21 publications

References 23 publications

Synthesis of Cyclic Peroxides

Synthesis of Cyclic Peroxides

Synthetic peroxides as antimalarials

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

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