50490-38-5Relevant academic research and scientific papers
Synthesis and structure-activity relationships for cytotoxicity and apoptosis-inducing activity of (+)-halichonine B
Hayakawa, Ichiro,Nakamura, Tomomi,Ohno, Osamu,Suenaga, Kiyotake,Kigoshi, Hideo
, p. 9969 - 9976 (2015/10/12)
Halichonine B is a sesquiterpene alkaloid isolated from the marine sponge Halichondria okadai Kadota. Halichonine B has exhibited cytotoxicity against mammalian cancer cells and induced apoptosis in the human leukemia cell line HL60. Here we established a practical route for the synthesis of halichonine B and its analogues, and we evaluated their biological activities. It was revealed that the secondary amino groups in the side chain portion are important for the strong cytotoxicity of halichonine B and that the N11-prenyl group is unimportant. Halichonine B and its analogues were also observed to induce apoptosis in HL60 cells.
Superacidic cyclisation-lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers
Serebryakov, Edward P.,Gamalevich, Galina D.,Kulcitki, Veacheslav N.,Ungur, Nicon D.,Vlad, Pavel F.
, p. 59 - 60 (2007/10/03)
(±)-α-Cyclogeraniol and (±)-drim-7-en-11-ol acetates obtained via the FSO3H-induced cyclisation of geraniol and (E)-farnesol and subsequent acetylation were hydrolysed in the presence of hog pancreas lipase (PPL) to afford (R)-(+)-α-cyclogeraniol (ee ～30% at the optimal conversion C = 20±2%) and (5R,9R,10R)-(+)-drim-7-en-11-ol (ee 78.5% at C = 30%), respectively; (±)-15-acetoxyisoagath-12-ene, obtained similarly from all-E-geranylgeraniol, is resistant to PPL-mediated hydrolysis, but is hydrolysed in the presence of lipase from Candida cylindracea to afford (10S,14R)-(-)-isoagath-12-en-15-ol of 69-80% ee in ～3% yield.
