Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols |
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| Authors: | Chen Bi-Shuang Yang Long-He Ye Jian-Liang Huang Tao Ruan Yuan-Ping Fu Jin Huang Pei-Qiang |
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| Institution: | aDepartment of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China;bDepartment of Pharmaceutical Sciences, Medical College, Xiamen University, Xiamen, Fujian 361005, PR China |
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| Abstract: | An improved four-step approach for the stereoselective synthesis of long-chain anti-2-amino-3-alkanols is described. Using this method, the syntheses of antiproliferative (antitumoral) compounds, spisulosine (ES-285, 2), clavaminols A and B (3 and 4), the deacetylated products of clavaminols H and N (7 and 8), as well as (2S,3R)-2-aminododecan-3-ol (9) and xestoaminol C (10), have been achieved in excellent diastereoselectivities. In vitro study showed that these compounds induced cell death and dose-dependently inhibited cell proliferation in human glioblastoma cell line SHG-44, indicating the anti-tumor property of this series of compounds. |
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| Keywords: | Marine compound Enantioselective synthesis One-pot reaction 1-Deoxy-sphingoid bases Cell proliferation |
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