engleski

The novel 4, 5-didehydro-L-ascorbic acid derivatives: synthesis, X-ray crystal structure study and cytostatic activity evaluations

The novel 6-substituted 4, 5-didehydro-L-ascorbic acid derivatives (11-13) were prepared by elimination and subsequent substitution reaction of the starting 5, 6-ditosyl-L-ascorbic acid (10). The exact stereostructure of the 5, 6-epoxy derivative of L-ascorbic acid (4) was determined by its X-ray crystal structure analysis. Z- and E- configurations of the C4=C5 double bond of compounds 11-13 were deduced from their one- and twodimensional 1H and 13C NMR spectra and conectivities in NOESY and HMBC spectra. Compounds 2-13 were evaluated for their cytostatic activity against malignant human tumor cell lines: cervical carcinoma (HeLa), breast carcinoma (MCF-7), pancreatic carcinoma (MiaPaCa-2) and colon carcinoma (SW620), and compared to their activities to normal human fibroblast cells (WI-38).

derivatives of 4 ; 5-didehydro-L-ascorbic acid ; X-ray crystal structure analysis ; antitumor activities ; 1H and 13C NMR

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