103292-13-3Relevant articles and documents
STEROIDS AND PROTEIN-CONJUGATES THEREOF
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Paragraph 0729-0731, (2018/05/27)
Described herein protein steroid conjugates that are useful, for example, for the target-specific delivery of glucocorticoids (GCs) to cells.
Glycosylated metal chelators as anti-parasitic agents with tunable selectivity
Reddy, Andrew,Sangenito, Leandro Stefano,Guedes, Arthur De Azevedo,Branquinha, Marta Helena,Kavanagh, Kevin,McGinley, John,Dos Santos, André Luis Souza,Velasco-Torrijos, Trinidad
supporting information, p. 5297 - 5307 (2017/04/27)
Trypanosoma cruzi and Leishmania amazonensis are the causative agents of Chagas' disease and leishmaniasis, respectively. These conditions affect millions of people worldwide, especially in developing countries. As such, there is an urgent need for novel, efficient and cost-effective treatments for these diseases, given the growing resistance and side-effects of current therapies. This work details the synthesis and evaluation of the anti-parasitic activity of novel amino- and iminopyridyl metal chelators, their glycosylated derivatives and some of their metal complexes. Our results revealed the potent and metal-dependent activity for the aminopyridyl compounds: Cu(ii) complexes were most effective against T. cruzi trypomastigotes, while Zn(ii) complexes presented excellent activity against L. amazonensis promastigotes. In addition, the compounds showed excellent selectivity indexes and very low relative toxicity as judged by in vitro and in vivo studies, respectively, using RAW macrophages and Galleria mellonella larvae model.
Analogs of anthocyanins with a 3′,4′-dihydroxy substitution: Synthesis and investigation of their acid-base, hydration, metal binding and hydrogen-donating properties in aqueous solution
Mora-Soumille, Nathalie,Al Bittar, Sheiraz,Rosa, Maxence,Dangles, Olivier
, p. 7 - 15,9 (2020/07/31)
Glycosides of hydroxylated flavylium ions are proposed as pertinent analogs of anthocyanins, a major class of polyphenolic plant pigments. Anthocyanins with a 3′,4′-dihydroxy substitution on the B-ring (catechol nucleus) are especially important for their metal chelating and electron-donating (antioxidant) capacities. In this work, an efficient chemical synthesis of 3′,4′-dihydroxy-7-O-β-d-glucopyranosyloxyflavylium chloride and its aglycone is reported. Then, the ability of the two pigments to undergo proton transfer (formation of colored quinonoid bases) and add water (formation of a colorless chalcone) is investigated: at equilibrium the colored quinonoid bases (kinetic products) are present in very minor concentrations (3+, the Al3+-glucoside complex is more stable than the Al3+-aglycone complex due to the higher sensitivity of the latter to water addition and conversion into the corresponding chalcone. Finally, the glucopyranosyloxyflavylium ion and its aglycone are compared for their ability to reduce the 1,1-diphenyl-2-picrylhydrazyl radical in a mildly acidic water/MeOH (1:1) mixture as a first evaluation of their antioxidant activity. Glycosidation at C7-OH results in a lower rate constant of first electron transfer to DPPH and a lower stoichiometry (total number of 1,1-diphenyl-2-picrylhydrazyl radicals reduced per pigment molecule). Anthocyanins are difficult to extract from plants in substantial amount. However, the analogs investigated in this work are of easy access by chemical synthesis and express the physico-chemical properties typical of anthocyanins. They can thus be regarded as valuable models for investigating the coloring, metal-binding and antioxidant properties of these important natural pigments.
Synthesis and evaluation of 5-benzylidene(thio)barbiturate-β-d-glycosides as mushroom tyrosinase inhibitors
Yan, Qin,Cao, Rihui,Yi, Wei,Yu, Liang,Chen, Zhiyong,Ma, Lin,Song, Huacan
supporting information; experimental part, p. 4055 - 4058 (2010/04/02)
A series of 5-benzylidene(thio)barbiturate-β-d-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that most of compounds had more potent inhibitory activities than arbutin (IC50 8.4 mmol/L). Compound 12b was found to be the most potent inhibitor with IC50 value of 0.05 mmol/L. SARs analysis suggested that (1) 5-benzylidenethiobarbiturate substructures were efficacious for the inhibitory activity; (2) the lipophilic property of acetylated sugar moiety facilitated the inhibitory potency; (3) the hydroxyl group of 3′-configuration contributed to the increase of inhibitory effects. In addition, the inhibition mechanism study revealed that 5-benzylidene(thio)barbiturate-β-d-glycosides were irreversible inhibitors.
3-Methoxy-4-(2-nitrovinyl)phenyl glycosides as potential chromogenic substrates for the assay of glycosidases.
Patel,Richardson
, p. 241 - 249 (2007/10/02)
Selective glycosidation of 2,4-dihydroxybenzaldehyde with either 2,3,4, 6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide, 2-acetamido-3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl chloride, or 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide afforded the corresponding 4-O-glycosyl derivatives. Subsequent O-methylation, O-deacetylation, and condensation with nitromethane afforded the appropriate beta-glycoside of 3-methoxy-4-(2-nitrovinyl)phenol. The phenol is highly coloured at alkaline pH so that these glycosides may be suitable as chromogenic substrates for the assay of glycosidases.
