title: Diastereoselective synthesis and bioactivity of long-chain anti-2-amino-3-alkanols.
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.
authors.affiliation: Department 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.
authors.forename: Bi-Shuang
authors.initials: BS
authors.lastname: Chen
authors.forename: Long-He
authors.initials: LH
authors.lastname: Yang
authors.forename: Jian-Liang
authors.initials: JL
authors.lastname: Ye
authors.forename: Tao
authors.initials: T
authors.lastname: Huang
authors.forename: Yuan-Ping
authors.initials: YP
authors.lastname: Ruan
authors.forename: Jin
authors.initials: J
authors.lastname: Fu
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004305:Dose-Response Relationship, Drug; D006801:Humans; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000438:Alcohols; D000970:Antineoplastic Agents