Several novel C-pseudonucleosides bearing thiazolidin-4-one were synthesized by one-pot three-component condensation using unprotected sugar aldehyde at room temperature, and their effects on T cells, B cells, the cytokine secretion of IL-2, IL-4, and IFN-γ, T cell-associated molecules (CD3, CD4, CD8), and B cell-associated molecules (CD19) were first evaluated. The experimental data demonstrated that such thiazolidin-4-one C-pseudonucleosides hold potential as immunostimulating agents.
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| http://dx.doi.org/10.1021/ml200155k | DOI Listing |
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Synthesis of tetracyclic iminosugars fused benzo[e][1,3]thiazin-4-one and their HIV-RT inhibitory activity.
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Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China. Electronic address:
Several aza-C-pseudonucleosides bearing 1,3-benzothiazin-4-one (6 and 7) were prepared by the one-pot three-component condensation from the iminosugar aldehyde 3, amino acid ethyl/methyl ester hydrochlorides 4(a-c), and 2-mercaptobenzoic acid 5. After removal of Boc and the isopropylidene groups, the target novel tetracyclic iminosugars fused benzo[e][1,3]thiazin-4-one 1(a-c) and 2(a-b) were first afforded by the intramolecular cyclo-amidation reaction. Their structures were determined by their (1)H, (13)C NMR, and HRMS (ESI) spectra and X-ray.
View Article and Find Full Text PDFSynthesis of C-Pseudonucleosides Bearing Thiazolidin-4-one as a Novel Potential Immunostimulating Agent.
ACS Med Chem Lett
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Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science and Medical School, Hebei University, Baoding 071002, China.
Several novel C-pseudonucleosides bearing thiazolidin-4-one were synthesized by one-pot three-component condensation using unprotected sugar aldehyde at room temperature, and their effects on T cells, B cells, the cytokine secretion of IL-2, IL-4, and IFN-γ, T cell-associated molecules (CD3, CD4, CD8), and B cell-associated molecules (CD19) were first evaluated. The experimental data demonstrated that such thiazolidin-4-one C-pseudonucleosides hold potential as immunostimulating agents.
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