Synthesis of a novel ceramide analogue via Tebbe methylenation and evaluation of its antiproliferative activity.
[reaction: see text] A new analogue of (2S,3R)-ceramide (2) with a methylene group at C4 has been synthesized from d-tartaric acid (3) by using Tebbe methylenation as the key step. Compound 2 exhibited markedly higher antiproliferative activity on mouse embryonic fibroblast (MEF) cells than natural (2S,3R,4E)-ceramide (1).
Lu
Xuequan
X
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
Arthur
Gilbert
G
Bittman
Robert
R
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002518:Ceramides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D005347:Fibroblasts / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D013644:Tartrates / Q000737:chemistry
D000970:Antineoplastic Agents; C507267:C4-methylene D-erythro-N-octanoylceramide; D002518:Ceramides; D013644:Tartrates; C029768:tartaric acid