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Communication | Regular issue | Vol 31, No. 6, 1990, pp.1011-1016
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5396
Acid Degradation Products of Qinghaosu and Their Structure-Activity Relationships

Yasuhiro Imakura,* Katsutoshi Hachiya, Tomomi Ikemoto, Shinsuke Yamashita, Masaru Kihara, Shigeru Kobayashi, Tetsuro Shingu, Wilbur K. Milhous, and Kuo-Hsiung Lee

*Faculty of Sciences, Naruto University of Education, Takashima, Naruto-shi, Tokushima 772- , Japan


Treatment of qinghaosu (1) with acid yielded 1’,2’,4’-trioxanes (5 and 8), endoperoxides (6 and 9), and diketones (7 and 10). Structures of 5, 6, 7, 8, 9, and 10 were assigned based on their physical and spectral data. Structure-activity correlation among these compounds indicated the steric requirement of the 1’,2’,4’-trioxane ring system as found in 1 for potent antimalarial activity.