Synthesis and characterization of new aromatic aldehyde/ketone 4-(β-d-glucopyranosyl)thiosemicarbazones

Tenchiu, Alia-Cristina; Kostas, Ioannis D.; Kovala‐Demertzi, Dimitra; Terzis, Aris

doi:10.1016/j.carres.2009.05.010

Cited by 27 publications

(4 citation statements)

References 30 publications

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“…NMR spectroscopy confirmed the formation of E isomers which is a most favored confirmation and reported in similar type of reactions (Gumina and Chu, 2003; Tenchiu et al, 2009). An excellent example of the reactivity of N - N binucleophiles is attributed in the reaction of 1 and 2 with 3-methyl-1 H -pyrazole-5-amine yielding 7 and 14 respectively.…”

Section: Introductionsupporting

confidence: 78%

Synthesis, Antiviral, and Antimicrobial Evaluation of Benzyl Protected Diversified C-nucleosides

et al. 2018

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Formyl glycals are the versatile synthetic intermediates and can serves as precursor for the synthesis of various C and N-nucleosides. Due to the presence of electron donating and electron withdrawing character on formyl sugars which makes the molecule more susceptible to nucleophilic attack. Utilizing same strategy, we propose the synthesis of diversified C-nucleosides (3-14) by reaction with N,N dinucleophiles. These nucleoside analogs were than tested against viral, bacterial and fungal strains.

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Section: Introductionsupporting

confidence: 78%

Synthesis, Antiviral, and Antimicrobial Evaluation of Benzyl Protected Diversified C-nucleosides

et al. 2018

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“…In the past some papers have been published for the synthesis of aldehyde/ketone (per-O-acetylated glycopyranosyl)thiosemicarbazones[231825282930]. The main synthetic step for the synthesis of these molecules is being the reaction of (per- O -acetylglycosyl)thiosemicarbazide with the coresponding carbonyl compounds.…”

mentioning

confidence: 99%

Synthesis, structure and antioxidant activity of (tetra-O-acetyl-β-D-galactopyranosyl)thiosemicarbazones of substituted benzaldehydes

Thành¹,

Hoai²

2012

Indian J Pharm Sci

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Some new substituted benzaldehyde (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) thiosemicarbazones were synthesised by reaction of 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl thiosemicarbazide and different substituted benzaldehydes. The reaction was performed using conventional and microwave-assisted heating methods. The structures of thiosemicarbazones were confirmed by spectroscopic (IR, 1 H NMR, 13 C NMR and MS) method. 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.

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“…The stereochemistry at the CϭN bond of the thiosemicarbazone derivatives was established by 1 H NMR spectroscopy. The value of the chemical shift of the NH (9 to 12 ppm) is indicative of (E) configuration (60). Some semicarbazones were also synthesized, according to a previously described procedure (61), for comparison of the activity of semicarbazones with that of the thiosemicarbazones.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a Sugar-Based Thiosemicarbazone Series and Structure-Activity Relationship versus the Parasite Cysteine Proteases Rhodesain, Cruzain, and Schistosoma mansoni Cathepsin B1

Fonseca

Cruz

Villela

et al. 2015

Antimicrob Agents Chemother

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gThe 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 (IC 50 s) of <10 M. Among the compounds tested, the thiosemicarbazone derivative of peracetylated galactoside (compound 4i) was discovered to be a potent rhodesain inhibitor (IC 50 ‫؍‬ 1.2 ؎ 1.0 M). 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. N ew drugs for parasitic diseases are urgently needed, but these globally important infections are often "neglected" because they most commonly afflict poor and marginalized communities. Current therapies are limited by poor efficacy, toxicity, high costs, and parasite resistance. Chagas disease, African sleeping sickness, and schistosomiasis are examples of diseases for which new therapies are needed (1, 2). Among the most studied and exploited molecular targets for these diseases are cysteine proteases. These enzymes have essential roles in parasite nutrition, immune evasion, host cell invasion, and metacyclogenesis (3-6). Indeed, the cysteine proteases cruzain, rhodesain, and Schistosoma mansoni CB1 (SmCB1) from Trypanosoma cruzi, Trypanosoma brucei, and S. mansoni, respectively, are validated molecular targets and have been the subject of numerous medicinal chemistry projects (7-17) that have yielded trypanocidal inhibitors, both in parasite culture and in animal models of infection (13,15,(18)(19)(20)(21).The diverse inhibitors of these enzymes comprise compound classes which bind noncovalently (11, 12) and scaffolds containing a "warhead" that binds covalently to the catalytic cysteine. Within the latter category, vinylsulfones (8,(22)(23)(24)(25), oxy-methyl ketones (7, 26), nitriles (16), epoxides, and thiosemicarbazones (13-15, 27-29) have been described previously. Thiosemicarbazones present as advantages their low molecular weight, low cost of synthesis, and nonpeptidic nature (27). Greenbaum and coworkers synthesized and evaluated the cysteine protease inhibitory and antiparasitic activities of a library of thiosemicarbazones, with promising results (13). According to those authors, the thiosemicarbazones are...

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Synthesis and characterization of new aromatic aldehyde/ketone 4-(β-d-glucopyranosyl)thiosemicarbazones

Cited by 27 publications

References 30 publications

Synthesis, Antiviral, and Antimicrobial Evaluation of Benzyl Protected Diversified C-nucleosides

Synthesis, Antiviral, and Antimicrobial Evaluation of Benzyl Protected Diversified C-nucleosides

Synthesis, structure and antioxidant activity of (tetra-O-acetyl-β-D-galactopyranosyl)thiosemicarbazones of substituted benzaldehydes

Synthesis of a Sugar-Based Thiosemicarbazone Series and Structure-Activity Relationship versus the Parasite Cysteine Proteases Rhodesain, Cruzain, and Schistosoma mansoni Cathepsin B1

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