Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols

Amewu, Richard K.; Gibbons, Peter; Mukhtar, Amira; Stachulski, Andrew V.; Ward, Stephen A.; Hall, C. Richard; Rimmer, Karen; Davies, Jill; Vivas, Livia; Bacsa, John; Mercer, Amy E.; Nixon, Gemma L.; Stocks, Paul A.

doi:10.1039/b924319d

Cited by 17 publications

(12 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A C C E P T E D ACCEPTED MANUSCRIPT 83 group R 2 such as ketone, ester, amide and nitro (Scheme 134). 230 The electrophilic dialkylphosphonyl radicals selectively added to the β-position of the aryl vinyl to form benzyl radicals.…”

Section: Scheme 133mentioning

confidence: 98%

“…82 They also employed this reaction in the synthesis of other 1,2,4-trioxepanes derivatives. 83 The Yadav group reported AgNO 3 -catalyzed oxysulfonylation of alkenes in the presence of air and K 2 S 2 O 8 as oxidants. 84 Sulfenyl radicals generated from thiophenols added to alkenes followed by oxidation with oxygen to from β-hydroxysulfides 72 and then with K 2 S 2 O 8 to form …”

Section: A N U S C R I P Tmentioning

confidence: 99%

See 1 more Smart Citation

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

et al. 2015

View full text Add to dashboard Cite

Section: Scheme 133mentioning

confidence: 98%

Section: A N U S C R I P Tmentioning

confidence: 99%

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

et al. 2015

View full text Add to dashboard Cite

“…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.

180

136

View full text Add to dashboard Cite

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.

show abstract

“…In the second step (condensation), cyclopentanone, cyclohexanone, tert -butylcyclohexanone, 1,4-cyclohexanedione, cyclododecanone, and adamantanone were employed. 1,2,4-Trioxanes 339 were prepared in 25–68% yields in two steps [120,393]. …”

Section: Reviewmentioning

confidence: 99%

“…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.

View full text Add to dashboard Cite

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.

show abstract

Synthesis, in vitro and in vivo antimalarial assessment of sulfide, sulfone and vinyl amide-substituted 1,2,4-trioxanes prepared via thiol-olefin co-oxygenation (TOCO) of allylic alcohols

Cited by 17 publications

References 44 publications

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S–C and P–C bonds

Rearrangements of organic peroxides and related processes

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

Contact Info

Product

Resources

About