title: Increasing the amphiphilicity of an estradiol based steroid structure by Barbier-allylation--ring-closing metathesis--dihydroxylation sequence.
abstract: Polyhydroxylated steroids, such as brassinosteroids, phytoecdysteroids and steroid saponins, are structurally attractive compounds possessing a number of interesting biological properties. Accordingly, development of synthetic procedures to build steroid based structures mimicking the naturally occurring hydrophilic steroids is of topical interest. In the present work, a D-secoestrone derivative was modified further by Barbier-allylation - ring-closing metathesis - dihydroxylation sequence with the aim to prepare steroid based structures with limited hydrophilicity. A straightforward synthesis route was developed with the isolated yield for each step ranging from good to excellent. All compounds prepared were fully characterized by NMR spectroscopic techniques and completely assigned (1)H and (13)C spectra are reported herein. Finally, the effects of the synthesized amphiphilic steroid derivatives on the proliferation of cancer cells are reported and discussed.
authors.affiliation: Laboratory of Organic Chemistry, Åbo Akademi University, Åbo, Finland.
authors.forename: Tiina
authors.initials: T
authors.lastname: Saloranta
authors.forename: István
authors.initials: I
authors.lastname: Zupkó
authors.forename: Jani
authors.initials: J
authors.lastname: Rahkila
authors.forename: Gyula
authors.initials: G
authors.lastname: Schneider
authors.forename: János
authors.initials: J
authors.lastname: Wölfling
authors.forename: Reko
authors.initials: R
authors.lastname: Leino
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D060406:Brassinosteroids / Q000737:chemistry; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D026461:Ecdysteroids / Q000737:chemistry; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D060406:Brassinosteroids; D026461:Ecdysteroids; D012503:Saponins; D013501:Surface-Active Agents; D004958:Estradiol