19879-84-6Relevant articles and documents
Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions
Fulton,Stoddart
, p. 8309 - 8319 (2001)
The syntheses of homogeneous cyclodextrin-based carbohydrate clusters, persubstituted with β-D-thioglucosyl or D-thiolactosyl residues on either (a) the primary face, (b) the secondary face, or (c) both the primary and the secondary faces of their cyclodextrin tori, are described. The key step in the synthetic methodology, namely the attachment of the carbohydrate residues to the cyclodextrin torus, proceeds in moderate-good yields (42-70%) by the photoaddition of thiol groups, positioned at the anomeric centers of the carbohydrate residues, to allyl ether functions on the cyclodextrins. Facile removal of protecting groups then affords the free cluster compounds. Extensive 1-D and 2-D NMR spectroscopic investigations were performed on these compounds to determine their structures and establish their homogeneities, and a brief computer molecular modeling study allowed estimates of the dimensions of the clusters to be determined.
Synthesis and Biochemical Evaluation of an Artificial, Fluorescent Glucosinolate (GSL)
Glindemann, Carina Patrizia,Backenk?hler, Anita,Strieker, Matthias,Wittstock, Ute,Klahn, Philipp
, p. 2341 - 2345 (2019)
The synthesis of the first example of a fluorescent glucosinolate (GSL)–BODIPY conjugate based on an azide-containing artificial GSL precursor (GSL-N3) is reported. Biochemical evaluation of the artificial GSLs revealed that the compounds are converted to the corresponding isothiocyanates in the presence of myrosinase. Furthermore, myrosinase-catalyzed hydrolysis in the presence of plant specifier proteins yielded the expected alternative products, namely nitriles. The easy assembly of the fluorescent GSL–BODIPY conjugate by click chemistry from GSL-N3 holds potential for application as a fluorescence labeling tool to investigate GSL-associated processes.
Large-scale synthesis of thio-glucose-conjugated chlorin E6 for photodynamic therapy
Hyakumura, Keisuke,Kataoka, Hiromi,Kodama, Shintaro,Masuda, Masato,Narumi, Atsushi,Nomoto, Akihiro,Ogawa, Akiya,Okamoto, Yoshiharu,Osaki, Tomohiro,Tanaka, Mamoru,Yamaguchi, Hiroaki,Yano, Shigenobu,Yoshimura, Tomokazu
, (2021/06/21)
Chlorin e6 is a heterocycle exhibiting spectral absorption in the 600-700 nm wavelength range used for photodynamic therapy (PDT). Herein, a sugar-conjugated chlorin e6 derivative was synthesized on a large scale. An alkyl spacer was fabricated by controlling the alkoxylation conditions between the thio-sugar and chlorin e6 and thio-glucose-conjugated chlorin e6 was successfully synthesized.
Preparation method and application of peracetyl-protected 1-thioglucose and glucose 1-mercaptan
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Paragraph 0060-0062, (2021/03/24)
The invention belongs to the technical field of medicine and sugar chemical synthesis, and particularly relates to a preparation method and application of peracetyl-protected 1-thioglucose and glucose1-mercaptan. The preparation method comprises the following steps of reacting peracetyl-protected glucose and potassium thioacetate in an organic solvent at the temperature of between normal temperature and 50 DEG C under the catalysis of boron trifluoride diethyl ether for 4-8 hours to obtain peracetyl-protected 1-thioglucose; and dissolving the prepared peracetyl-protected 1-thioglucose in dimethylformamide, and removing thioacetyl by using hydrazine hydrate to obtain peracetyl-protected glucose 1-mercaptan. The peracetyl-protected glucose 1-mercaptan can be used for further preparing auronofen and gliclazide thioglycoside analogues. The method disclosed by the invention is mild in reaction condition, simple and convenient to operate, low in synthesis cost, relatively green and high inyield, the auronofen is a medicine for treating rheumatic arthritis, and the gliflozin thioglycoside analogue is a potential medicine for treating type 2 diabetes mellitus.
8-Hydroxyquinoline glycoconjugates containing sulfur at the sugar anomeric position—synthesis and preliminary evaluation of their cytotoxicity
Erfurt, Karol,Hadasik, Agnieszka,Krawczyk, Monika,Pastuch-Gawo?ek, Gabriela
, (2020/09/18)
One of the main factors limiting the effectiveness of many drugs is the difficulty of their delivery to their target site in the cell and achieving the desired therapeutic dose. Moreover, the accumulation of the drug in healthy tissue can lead to serious side effects. The way to improve the selectivity of a drug to the cancer cells seems to be its conjugation with a sugar molecule, which should facilitate its selective transport through GLUT transporters (glucose transporters), whose overexpression is seen in some types of cancer. This was the idea behind the synthesis of 8-hydroxyquinoline (8-HQ) derivative glycoconjugates, for which 1-thiosugar derivatives were used as sugar moiety donors. It was expected that the introduction of a sulfur atom instead of an oxygen atom into the anomeric position of the sugar would increase the stability of the obtained glycoconjugates against untimely hydrolytic cleavage. The anticancer activity of new compounds was determined based on the results of the MTT cytotoxicity tests. Because of the assumption that the activity of this type of compounds was based on metal ion chelation, the effect of the addition of copper ions on cell proliferation was tested for some of them. It turned out that cancer cells treated with glycoconjugates in the presence of Cu2+ had a much slower growth rate compared to cells treated with free glycoconjugates in the absence of copper. The highest cytotoxic activity of the compounds was observed against the MCF-7 cell line.
