Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moiety
Article title: Synthesis and Biological Activity of Novel Thiazolidin-4-ones with a Carbohydrate MoietyJournal title: Carbohydrate Research
Authors: Hua Chen, Lingling Jiao, Zaihong Guo, Xiaoliu Li *, Cuilan Ba, Jinchao Zhang
Online publication complete: 19-SEP-2008
DOI information: 10.1016/j.carres.2008.09.004
Available online at: [url]http://dx.doi.org/10.1016/j.carres.2008.09.004[/url]
Some novel 2-aryl-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl] thiazolidin-4-ones were synthesized by the three-component condensation of an amino sugar 1, an aromatic aldehyde 2, and mercaptoacetic acid 3 in the presence of DCC and DMAP at room temperature. Two diastereoisomers 4 and 5 were afforded as the main products in totally isolated yields of 25.4–70%. The reaction was carried out with almost no observed stereoselectivity except in the case of 2c, which showed a moderate stereoselectivity. The structures of the new compounds were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration of the newly generated chiral carbon (C-2) in the thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 5d and the comparison of their corresponding NMR signals. The antitumor (human cervical cancer cells) activity and the inhibition against the glycosidases (α-glucosidase, β-glucosidase, α-amylase) have been evaluated for the new compounds, some of which exhibited antitumor activity.
Article Outline
1. Introduction
2. Results and discussion
2.1. The synthesis of thiazolidin-4-ones bearing a sugar moiety
2.2. The structure of the compounds 4 and 5
2.3. Biological activities
3. Experimental
3.1. General methods
3.2. General procedure for the synthesis of thiazolidin-4-ones
3.2.1. (2S)-2-(4-Chlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (4a)
3.2.2. (2R)-2-(4-Chlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (5a)
3.2.3. (2S)-2-(2,6-Dichlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (4b)
3.2.4. (2R)-2-(2,6-Dichlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (5b)
3.2.5. (2S)-2-(2-Chlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (4c)
3.2.6. (2R)-2-(2-Chlorophenyl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (5c)
3.2.7. (2S)-2-(Benzo[d][1,3]dioxol-5-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (4d)
3.2.8. (2R)-2-(Benzo[d][1,3]dioxol-5-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (5d)
3.2.9. (2S)-2-(1-Ethyl-1H-imidazol-2-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (4e)
3.2.10. (2R)-2-(1-Ethyl-1H-imidazol-2-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (5e)
3.2.11. (2S)-2-(Pyridin-4-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (4f)
3.2.12. (2R)-2-(Pyridin-4-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (5f)
3.2.13. (2S)-2-(1H-Indole-3-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (4g)
3.2.14. (2R)-2-(1H-Indole-3-yl)-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl]thiazolidin-4-one (5g)
3.3. Single-crystal X-ray crystallographic analysis of 5d20
3.4. Biological activity assays
3.4.1. Inhibition of glycosidases
3.4.2. Antitumor activity
Supplementary data
Acknowledgements
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