Synthesis of some 2-C-alkyl-2,3-dideoxy-alpha,beta-L-glycero-tetrurono-1,4-lactones . Evaluation as antitumor agents.
A series of 3-C-alkyl-2,3-dideoxy-5-O-trityl-D-erythro-pentono-1,4-lactones were detritylated. The resultant free-hydroxy compounds were converted to their respective 2-C-alkyl-2,3-dideoxy-alpha,beta-L-glycero-tetrurono-1,4-lactones (L-sugar numbering) in a one-vessel reaction sequence of (a) conversion of the lactones to their aldonic acid sodium salts, (b) cleavage of the resulting aldonates with sodium metaperiodate, and (c) acidification, followed by acetylation, to give the title compounds. The unsubstituted tetrurono-1,4-lactones were inhibitory toward L1210 leukemia cells at concentrations in the 10(-4) M range.
Blazis
V J
VJ
Department of Chemistry, University of Tennessee, Knoxville 37996-1600.
Hawkins
E S
ES
Baker
D C
DC
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D007939:Leukemia L1210; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007783:Lactones