A convenient synthesis of novel thiazolidin-4-one-linked pseudodisaccharides by tandem Staudinger/aza-Wittig/cyclization and their biological evaluation.

Abstract

Novel thiazolidin-4-one-linked pseudodisaccharides 3-6 were synthesized by the one-pot tandem Staudinger/aza-Wittig/cyclization reaction at room temperature. The deacetylation of 3-6 afforded compounds 7-10, respectively. The structures of the new compounds were determined using single crystal X-ray crystallography, (1)H, (13)C, and 2D NMR spectroscopy, and HR mass spectrometry. The preliminary biological evaluation of compounds 7-10 showed that compounds 7aa, 8aa, 7ab, 8ab, 7bb and 8bb were found to have significant immunopotentiating activity. Yet none of these tested compounds have obvious inhibition against glycosidases or HIV reverse transcriptase, or show cancer cell growth inhibition.

• Authors: Xiaoliu Li, Qingmei Yin, Lingling Jiao, Zhanbin Qin, Junna Feng, Hua Chen, Jinchao Zhang, Ming Meng
• Journal: Carbohydrate research (Carbohydr Res) Vol. 346 Issue 3 Pg. 401-9 (Feb 15 2011) ISSN: 1873-426X [Electronic] Netherlands
• PMID: 21215390 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2010 Elsevier Ltd. All rights reserved.

Chemical References

• Antineoplastic Agents
• Disaccharides
• Thiazoles
• HIV Reverse Transcriptase
• Glucosidases
• alpha-Amylases

Topics

• Animals
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Proliferation (drug effects)
• Cell Survival (drug effects)
• Cells, Cultured
• Crystallography, X-Ray
• Cyclization
• Disaccharides (chemical synthesis, chemistry, pharmacology)
• Enzyme Assays
• Glucosidases (antagonists & inhibitors)
• HIV Reverse Transcriptase (antagonists & inhibitors)
• HeLa Cells
• Humans
• Lymphocytes (cytology, drug effects, immunology)
• Mice
• Mice, Inbred BALB C
• Molecular Conformation
• Stereoisomerism
• Thiazoles (chemical synthesis, chemistry, pharmacology)
• alpha-Amylases (antagonists & inhibitors)