title: 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.affiliation: Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, China. lixl@hbu.cn
authors.forename: Xiaoliu
authors.initials: X
authors.lastname: Li
authors.forename: Qingmei
authors.initials: Q
authors.lastname: Yin
authors.forename: Lingling
authors.initials: L
authors.lastname: Jiao
authors.forename: Zhanbin
authors.initials: Z
authors.lastname: Qin
authors.forename: Junna
authors.initials: J
authors.lastname: Feng
authors.forename: Hua
authors.initials: H
authors.lastname: Chen
authors.forename: Jinchao
authors.initials: J
authors.lastname: Zhang
authors.forename: Ming
authors.initials: M
authors.lastname: Meng
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D018360:Crystallography, X-Ray; D003500:Cyclization; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D057075:Enzyme Assays; D005959:Glucosidases / Q000037:antagonists & inhibitors; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors; D006367:HeLa Cells; D006801:Humans; D008214:Lymphocytes / Q000166:cytology / Q000187:drug effects / Q000276:immunology; D051379:Mice; D008807:Mice, Inbred BALB C; D008968:Molecular Conformation; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000516:alpha-Amylases / Q000037:antagonists & inhibitors
chemical_list: D000970:Antineoplastic Agents; D004187:Disaccharides; D013844:Thiazoles; D054303:HIV Reverse Transcriptase; D005959:Glucosidases; D000516:alpha-Amylases