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Short Paper | Regular issue | Vol 89, No. 4, 2014, pp.1055-1064
Published online, 14th February, 2014
DOI: 10.3987/COM-14-12948
Synthesis and Antimalarial Activity of Some Neocryptolepine Analogues Carrying a Multifunctional Linear and Branched Carbon-Side Chains

Elkhabiry Shaban, Kathryn J. Wicht, Ning Wang, Zhen-Wu Mei, Ikuya Hayashi, Ahmed Abdel Aleem El Gokha, Marcel Kaiser, Ibrahim El Tantawy El Sayed, Timothy J. Egan,* and Tsutomu Inokuchi*

*Division of Chemsitry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan


The synthesis and in vitro antimalarial activity of several neocryptolepine analogues carrying either a linear or branched dibasic side chain at C11 are described. Many of these neocryptolepine analogues have low nanomolar antimalarial activity against the chloroquine-sensitive P. falciparum strain (NF54). The data also demonstrated that a branched structural motif is not superior for antimalarial activity over a linear side chain, but their thioureido derivatives showed lower cytotoxicity than the linear one. Ureido and thioureido derivatives also showed stronger β-haematin inhibition than the corresponding free amines.