New stereocontrolled synthesis and biological evaluation of 5-(1'-hydroxyalkyl)-3-methylidenetetrahydro-2-furanones as potential cytotoxic agents.
A series of 3-methylidenetetrahydro-2-furanones 7 bearing various hydroxyalkyl substituents in position 5 were synthesized using novel diastereo- and enantioselective methodology. In vitro cytotoxicity data demonstrated that all prepared compounds were active against L-1210 and HL-60 tissue culture cells with 7e being the most potent (IC(50) = 6.9 microM). Also an increase in activity with an increase in lipophilicity of the substituents in the order H < alkyl < phenyl was observed.
Janecki
Tomasz
T
Institute of Organic Chemistry, Technical University, Zeromskiego 116, 90-924 Łódź, Poland. tjanecki@ck-sg.p.lodz.pl
Błaszczyk
Edyta
E
Studzian
Kazimierz
K
Rózalski
Marek
M
Krajewska
Urszula
U
Janecka
Anna
A
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007093:Imidazoles / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
C450157:5-(hydroxyphenylmethyl)-3-methylidenetetrahydro-2-furanone; D000970:Antineoplastic Agents; D007093:Imidazoles; C115705:ciproxifan; D015107:4-Butyrolactone