Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Department of Pediatrics, University of California, San Diego, School of Medicine , 9500 Gilman Drive 0741, La Jolla, California 92093, United States.
J Am Chem Soc. 2016 Jun 15;138(23):7268-71. doi: 10.1021/jacs.6b03899. Epub 2016 May 31.
7,20-Diisocyanoadociane, a scarce marine metabolite with potent antimalarial activity, was synthesized as a single enantiomer in 13 steps from simple building blocks (17 linear steps). Chemical synthesis enabled identification of isocyanoterpene antiplasmodial activity against liver-stage parasites, which suggested that inhibition of heme detoxification does not exclusively underlie the mechanism of action of this class.
7,20-二异氰基荜澄茄烷,一种具有强效抗疟活性的罕见海洋代谢产物,由简单的构建块通过 13 步反应(17 步线性反应)合成得到单一的对映异构体。化学合成使人们能够识别出异氰基萜类化合物对肝期寄生虫的抗疟活性,这表明血红素解毒抑制并非此类化合物作用机制的唯一基础。