Present address: Division of Medical Oncology, Department of Medicine, School of Medicine, University of Colorado Denver, Aurora, CO 80045 USA.
Regioselective Synthesis of Novel 3-Thiazolidine Acetic Acid Derivatives from Glycosido Ureides
Article first published online: 24 OCT 2011
© 2011 John Wiley & Sons A/S
Chemical Biology & Drug Design
Volume 78, Issue 6, pages 969–978, December 2011
How to Cite
Li, Y., Chen, W., Yang, X., Yu, G., Mao, M., Zhou, Y., Liu, T. and Li, Z. (2011), Regioselective Synthesis of Novel 3-Thiazolidine Acetic Acid Derivatives from Glycosido Ureides. Chemical Biology & Drug Design, 78: 969–978. doi: 10.1111/j.1747-0285.2011.01241.x
- Issue published online: 16 NOV 2011
- Article first published online: 24 OCT 2011
- Accepted manuscript online: 15 SEP 2011 12:00AM EST
- Received 9 January 2011, revised 23 August 2011 and accepted for publication 11 September 2011
- crystal structure;
- glycosido ureide;
A series of 3-thiazolidine acetic acid-2-(per-O-acetylglycosyl)-1′-imino-α-(substituted)-4-oxo ethyl ester derivatives (3a–t) were prepared via the reaction of substituted amino acid-N-[(per-O-acetylglycosylamino)thioxomethyl]-ethyl ester with ethyl bromoacetate. The crystal structure of 3-thiazolidine acetic acid-2-(2′,3′,4′,6′-tetra-O-acetyl-β-d-galactoyranosyl)-1′-imino-α-methyl-4-oxo ethyl ester 3g and 1H-13C HMBC (2D NMR experiments) measurements of 3-thiazolidine acetic acid-2-(2′,3′,4′,6′-tetra-O-acetyl-β-d-galactopyranosyl)-1′-imino-α-(1-methylthio)ethyl-4-oxo ethyl ester 3j revealed the exclusive regioselectivity during the closure of these rings toward the N-2 position of the thiourea moiety. Furthermore, the crystal structure of compound 3g showed that the attack of N-1 was blocked by sugar ring owing to the steric effect. The bioactivity data suggested that compound 2e has mild anticancer activity.