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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 18, Number 6
BKCSDE 18(6)
June 20, 1997 

Syntheses and Iron(Ⅱ) Induced Reactions of Phenyl-Substituted 1,2,4-Trioxanes
Chang Ho Oh, Gary H. Posner
Introduction of an alkyl substituent at the C4β position of antimalarial trioxanes has caused them to become more active in their antimalarial activity. We have designed a structurally simple 4β-phenyl substituted trioxane (3) as an active antimalarial since it can form a more stable carbon radical when reacting with ferrous bromide. The trioxane 3 has been prepared along with the corresponding isomer 4 according to the previously reported procedure. The synthesized trioxanes 3 and 4 were finally separated by using HPLC and assigned their stereochemistry by spectroscopy and X-ray crystallography. Their antimalarial activities were surprisingly low. The low activity was then rationalized based on the product distribution of the ferrous ion induced reaction of these trioxanes. These trioxanes with ferrous bromide did not produce any detectable amount of the corresponding C4-hydroxylated product, consistent with the fact that neither C4β-phenyl substituted nor C4α-phenyl substituted trioxane has any antimalarial activity. It implies that a C4 substituent of antimalarial trioxanes has to stabilize an adjacent carbon-centered radical in a specific stability range in order to show a good antimalarial activity. This study, combined with related studies, could help develop more potent antimalarial trioxanes.
644 - 648
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