May, 2003
Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes
JOURNAL OF MEDICINAL CHEMISTRY
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- Volume
- 46
- Number
- 10
- First page
- 1957
- Last page
- 1961
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1021/jm020387b
- Publisher
- AMER CHEMICAL SOC
Photooxygenation of 2-phenylnorbornene 1 in the presence of 30% aqueous hydrogen peroxide afforded 1,2-bishydroperoxide 3, which could be cycloalkylated on treatment with silver oxide and a 1,omega-diiodoalkane to provide the tricyclic peroxides 12. Trimethylsilylation of 3 followed by TMSOTf-catalyzed cyclocondensation with carbonyl compounds led to the formation of the tricyclic peroxides 14 containing a 1,2,4,5-tetroxepane structure. Photooxygenation of 1 in the presence of either unsaturated hydroperoxides or unsaturated alcohols followed by bis(collidine)iodine hexafluorophosphate promoted cyclization gave the corresponding cyclic peroxides 15-17. Several of these cyclic peroxides showed substantial antimalarial activity particularly in vitro.
- Link information
- ID information
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- DOI : 10.1021/jm020387b
- ISSN : 0022-2623
- eISSN : 1520-4804
- Web of Science ID : WOS:000182709200019