1997
DOI: 10.1016/s0968-0896(97)00079-5
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Trioxane dimers have potent antimalarial, antiproliferative and antitumor activities in vitro

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Cited by 53 publications
(49 citation statements)
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“…S -Oxidation of the arylthiotrioxanes 610 affords the corresponding arylsulfonyl trioxanes 611, which exhibit potent antimalarial activity 520,530 . Hydroxyl functions in substituents at positions 4 and 9 of tricyclic trioxanes 607 were utilized for tethering with bis(electrophiles), yielding antimalarial, antiproliferative and antitumor active trioxane dimers 471 . The cyclic enol ether 612, bearing highly sensitive styryl substituent at the ketone tether, was used for the synthesis of tetracyclic trioxane 613 (Scheme 173) 524 .…”
Section: B Peroxyacetalization Of Carbonyl Functions With Strained Ementioning
confidence: 99%
“…S -Oxidation of the arylthiotrioxanes 610 affords the corresponding arylsulfonyl trioxanes 611, which exhibit potent antimalarial activity 520,530 . Hydroxyl functions in substituents at positions 4 and 9 of tricyclic trioxanes 607 were utilized for tethering with bis(electrophiles), yielding antimalarial, antiproliferative and antitumor active trioxane dimers 471 . The cyclic enol ether 612, bearing highly sensitive styryl substituent at the ketone tether, was used for the synthesis of tetracyclic trioxane 613 (Scheme 173) 524 .…”
Section: B Peroxyacetalization Of Carbonyl Functions With Strained Ementioning
confidence: 99%
“…5). The first generation C-10 acetal derivatives, even though very simple in their synthesis had the disadvantage of being easily hydrolysed in water [64,65]. To overcome this problem of instability, Posner and coworkers have subsequently succeeded in converting C-10 acetate directly into C-10 non-acetal trioxane dimers [66].…”
Section: Inhibitors From Plantsmentioning
confidence: 99%
“…Further investigation of the mechanism of this transformation by treatment of the hydroperoxide 151, derived from methyl ester of artemisinic acid, with the Cu(II) catalyst in the presence of oxygen suggests that a thermally labile, ring-cleaved enol 152 is a key intermediate (Scheme 53) [107]. The diastereoisomeric alcohols 154, derived from dihydroartemisinic acid 153, are transformed into the ring D-contracted artemisinin analogues 155 on reaction in turn with singlet oxygen followed by Cu(II)(OTf) 2 Two series of dimers 149 and 150, derived from either tricylic trioxanes or dihydroartemisin, have been prepared by conventional chemistry and found to exhibit antipoliferative and antitumour as well as antimalarial activity [106]. Artemisitene 161, which is also extracted in significant quantities from A. annua, readily undergoes TiCl 4 -catalysed coupling with allyltrimethylsilane, or trimethylsilyl cyanide or trimethylsilyl enol ethers under Mukaiyama conditions affording some new artemisinin derivatives 162 (usually as a mixture of isomers) in which the C-9 side chain is modified (Scheme 57) [111].…”
Section: Scheme 44mentioning
confidence: 99%