title: Total synthesis and antiproliferative/cytotoxic profiling of 2-epi-jaspine B.
abstract: A straightforward access to 2-epi-jaspine B (4.HCl) has been developed. Key to the approach was the use of Overman rearrangement for the instalment of a stereocentre bearing a nitrogen atom. Subsequent rational execution of the stereoselective transformations furnished the functionalized scaffold 38, whose coupling with a lipophilic segment under Wittig conditions, followed by deprotection and a THF core construction, completed the convergent synthesis of 2-epimer of 1. The final anhydrophytosphingosine 4.HCl was screened for its antiproliferative/cytotoxic activity employing multiple human cancer cell lines. In vitro evaluation revealed that 2-epi-jaspine B exhibited significant antitumour growth inhibitory activity against all used cells.
authors.affiliation: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic.
authors.forename: Eva
authors.initials: E
authors.lastname: Mezeiová
authors.affiliation: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic. Electronic address: miroslava.martinkova@upjs.sk.
authors.forename: Miroslava
authors.initials: M
authors.lastname: Martinková
authors.affiliation: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic.
authors.forename: Kvetoslava
authors.initials: K
authors.lastname: Stanková
authors.affiliation: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic.
authors.forename: Milica
authors.initials: M
authors.lastname: Fabišíková
authors.affiliation: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic.
authors.forename: Jozef
authors.initials: J
authors.lastname: Gonda
authors.affiliation: Department of Pharmacology, Faculty of Medicine, P.J. Šafárik University, SNP 1, 040 66 Košice, Slovak Republic.
authors.forename: Martina
authors.initials: M
authors.lastname: Pilátová
authors.affiliation: Department of Pharmacology, Faculty of Medicine, P.J. Šafárik University, SNP 1, 040 66 Košice, Slovak Republic.
authors.forename: Gabriela
authors.initials: G
authors.lastname: Gönciová
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D006801:Humans; D020128:Inhibitory Concentration 50; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; C468594:pachastrissamine; D013110:Sphingosine
keywords: 2-epi-Jaspine B; Anhydrophytosphingosines; Antiproliferative/cytotoxic activity; Jaspine B; Overman rearrangement