Synthesis and characterization of new aromatic aldehyde/ketone 4-(β-d-glucopyranosyl)thiosemicarbazones
TL;DR: A series of 22 aromatic aldehyde/ketone 4-(beta-D-glucopyranosyl)thiosemicarbazones have been synthesized by condensation of 4-(per-O-acetylated-beta- D- glucopyrsyl)ThioseMICarbazide with an alde Hyde or a ketone, and then, deacetylation of the resulting product.
About: This article is published in Carbohydrate Research.The article was published on 2009-07-27. It has received 26 citations till now. The article focuses on the topics: Semicarbazone & Ketone.
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TL;DR: In this paper, the coordination chemistry of thiosemicarbazone ligands with three (tridentate) or four (tetradentate) potential donor atoms is described.
136 citations
TL;DR: Molecular modeling studies results corroborated experimental SAR results, suggesting their use in the design of new antifungal agents, suggesting high selectivity.
90 citations
TL;DR: The design, synthesis, and structure-activity relationships of glucose analogue inhibitors of glycogen phosphorylase were surveyed in this paper, where a number of glucose analogues were presented.
75 citations
TL;DR: The thiosemicarbazones and heterocyclic analogues have been shown to be both antitrypanocidal and inhibitory against parasite cysteine proteases and a series of compounds synthesized and evaluated against cruzain, rhodesain, and SmCB1 through biochemical assays revealed active compounds among this series.
Abstract: The pressing need for better drugs against Chagas disease, African sleeping sickness, and schistosomiasis motivates the search for inhibitors of cruzain, rhodesain, and Schistosoma mansoni CB1 (SmCB1), the major cysteine proteases from Trypanosoma cruzi, Trypanosoma brucei, and S. mansoni, respectively. Thiosemicarbazones and heterocyclic analogues have been shown to be both antitrypanocidal and inhibitory against parasite cysteine proteases. A series of compounds was synthesized and evaluated against cruzain, rhodesain, and SmCB1 through biochemical assays to determine their potency and structure-activity relationships (SAR). This approach led to the discovery of 6 rhodesain, 4 cruzain, and 5 SmCB1 inhibitors with 50% inhibitory concentrations (IC50s) of ≤ 10 μM. Among the compounds tested, the thiosemicarbazone derivative of peracetylated galactoside (compound 4i) was discovered to be a potent rhodesain inhibitor (IC50 = 1.2 ± 1.0 μM). The impact of a range of modifications was determined; removal of thiosemicarbazone or its replacement by semicarbazone resulted in virtually inactive compounds, and modifications in the sugar also diminished potency. Compounds were also evaluated in vitro against the parasites T. cruzi, T. brucei, and S. mansoni, revealing active compounds among this series.
53 citations
TL;DR: The antioxidant activity of these thiosemicarbazones was evaluated in vitro and in vivo, and it's shown that some of these compounds had significant antioxidant activity.
45 citations
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TL;DR: The average lengths of bonds involving the elements H, B, C, N, O, F, Si, P, S, Cl, As, Se, Br, Te, and l in organic compounds are reported in this article.
Abstract: The average lengths of bonds involving the elements H, B, C, N, O, F, Si, P, S, Cl, As, Se, Br, Te, and l in organic compounds are reported.
6,649 citations
TL;DR: In this paper, the average lengths for metal-ligand bonds are reported, together with some intraligand distances, for complexes of the d-and f-block metals, for 325 different bond types involving metal atoms bonded to H, B, C, N, O, F, Si, P, S, Cl, As, Se, Br, Te, or I atoms of the ligands.
Abstract: Average lengths for metal–ligand bonds are reported, together with some intraligand distances, for complexes of the d- and f-block metals. Mean values are presented for 325 different bond types involving metal atoms bonded to H, B, C, N, O, F, Si, P, S, Cl, As, Se, Br, Te, or I atoms of the ligands.
1,019 citations
TL;DR: The more significant bioactivities of a variety of semicarbazones (anti-protozoa, anticonvulsant) and thiosemicarbazone and their metal complexes are reviewed together with proposed mechanisms of action and structure-activity relationships.
Abstract: The more significant bioactivities of a variety of semicarbazones (anti-protozoa, anticonvulsant) and thiosemicarbazones (antibacterial, antifungal, antitumoral, antiviral) and their metal complexes are reviewed together with proposed mechanisms of action and structure-activity relationships. Clinical or potential pharmacological applications of these versatile compounds are discussed.
669 citations
240 citations
TL;DR: The kinetic, crystallographic binding, and physiological studies of a number of compounds, inhibitors of GP, are described, and the essential inhibitory and binding properties of specific compounds are analyzed in an effort to provide rationalizations for the affinities of these compounds and to exploit the molecular interactions that might give rise to a better inhibitor.
Abstract: The regulation of the hepatic glucose output through glycogenolysis is an important target for type 2 diabetes therapy Glycogenolysis is catalyzed in liver, muscle and brain by tissue specific isoforms of glycogen phosphorylase (GP) Because of its central role in glycogen metabolism, GP has been exploited as a model for structure-assisted design of potent inhibitors, which may be relevant to the control of blood glucose concentrations in type 2 diabetes Several regulatory binding sites have been identified in GP, such as the catalytic, the allosteric, and the inhibitor binding sites Protein crystallography has contributed significant structural information on the specificity and interactions that distinguish the binding sites, and also revealed a new unexpected binding site (new allosteric site) In this review, the kinetic, crystallographic binding, and physiological studies of a number of compounds, inhibitors of GP, are described, and the essential inhibitory and binding properties of specific compounds are analyzed in an effort to provide rationalizations for the affinities of these compounds and to exploit the molecular interactions that might give rise to a better inhibitor These studies have given new insights into fundamental structural aspects of the enzyme enhancing our understanding of how the enzyme recognizes and specifically binds ligands, that could be of potential therapeutic value in the treatment of type 2 diabetes
156 citations