Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates

Guilherme, Fernanda; Simonetti, Julia Évelin; Folquitto, Laís R. S.; Reis, Adriana Cotta Cardoso; Oliver, Josidel Conceição; Dias, Amanda Latércia Tranches; Dias, Danielle Ferreira; Carvalho, Diogo Teixeira; Brandão, Geraldo Célio; Souza, Thiago Belarmino de

doi:10.1016/j.molstruc.2019.02.045

Cited by 16 publications

(13 citation statements)

References 19 publications

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“…The respective ester (1 eq) and hydrazine hydrate 80% (5 eq) were stirred in etanol (25 mL) under reflux for 8–48 h. Then, the reaction mixtures were cooled to 20–25 °C and then kept at 2–8 °C for 24 h. The solid hydrazides were collected by vacumn filtration, purified by recrystallization in hot ethanol and used as such for the next reactions. The identities of the hydrazides were confirmed by comparison of their IR and NMR spectra to the literature data and were in full agreement [ 34 – 38 , 74 ].…”

Section: Methodssupporting

confidence: 65%

Evaluation of antiplasmodial activity in silico and in vitro of N-acylhydrazone derivatives

et al. 2022

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N-acylhydrazones are considered privileged structures in medicinal chemistry, being part of antimicrobial compounds (for example). In this study we show the activity of N-acylhydrazone compounds, namely AH1, AH2, AH4, AH5 in in vitro tests against the chloroquine-resistant strain of Plasmodium falciparum (W2) and against WI26 VA-4 human cell lines. All compounds showed low cytotoxicity (LC50 > 100 µM). The AH5 compound was the most active against Plasmodium falciparum, with an IC50 value of 0.07 μM. AH4 and AH5 were selected among the tested compounds for molecular docking calculations to elucidate possible targets involved in their mechanism of action and the SwissADME analysis to predict their pharmacokinetic profile. The AH5 compound showed affinity for 12 targets with low selectivity, while the AH4 compound had greater affinity for only one target (3PHC). These compounds met Lipinski's standards in the ADME in silico tests, indicating good bioavailability results. These results demonstrate that these N-acylhydrazone compounds are good candidates for future preclinical studies against malaria. Graphical Abstract

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Section: Methodssupporting

confidence: 65%

Evaluation of antiplasmodial activity in silico and in vitro of N-acylhydrazone derivatives

et al. 2022

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“…All deuterated solvents were purchased from Cambridge Isotope Laboratories. 3-Bromobenzohydrazide ( 3.0 ), 4-bromobenzohydrazide ( 3.4 ), 2-hydroxy-5-bromobenzohydrazide ( 3.5 ), 2-hydroxy-3,5-dibromobenzohydrazide ( 3.6 ), 3-quinolinecarbohydrazide ( 3.7 ), 3,5-dibromobenzohydrazide ( 3.9 ), 4-cyanobenzohydrazide ( 3.11 ), 4-trifluoromethylbenzohydrazide ( 3.13 ), 4-fluorobenzohydrazide ( 3.20 ), 4-aminobenzohydrazide (3.24) , 4-acetamidobenzohydrazide ( 3.26 ), 2-methylbenzohydrazide ( 3.27 ), and 2-benzyloxy-3,5-dibromobenzaldehyde ( 4.1 ) were synthesized by the literature methods.…”

Section: Methodsmentioning

confidence: 99%

SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents

et al. 2019

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Recently, the fungal sphingolipid glucosylceramide (GlcCer) synthesis has emerged as a highly promising new target for drug discovery of next-generation antifungal agents, and we found two aromatic acylhydrazones as effective inhibitors of GlcCer synthesis based on HTP screening. In the present work, we have designed libraries of new aromatic acylhydrazones, evaluated their antifungal activities (MIC80 and time-kill profile) against C. neoformans, and performed an extensive SAR study, which led to the identification of five promising lead compounds, exhibiting excellent fungicidal activities with very large selectivity index. Moreover, two compounds demonstrated broad spectrum antifungal activity against six other clinically relevant fungal strains. These five lead compounds were examined for their synergism/cooperativity with five clinical drugs against seven fungal strains, and very encouraging results were obtained; e.g., the combination of all five lead compounds with voriconazole exhibited either synergistic or additive effect to all seven fungal strains.

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“…First, eugenol ( 1 ) and the other phenols ( 2 – 6 ) were alkylated from the Williamson synthesis, using propargyl chloride to provide the alkynes 7 – 12 by the method described by Achard et al (2011). In parallel, D‐glucose ( 13 ) was converted to its peracetylated derivative ( 14 ) after its reaction with acetic anhydride, which subsequently provided the acetobromoglucoside ( 15 ) after reaction with hydrobromic acid and acetic acid (Guilherme et al, 2019). The reaction of 15 with sodium azide led to the α‐glucosyl azide 16, which was employed in the next step without previous purification (Pote et al, 2018).…”

Section: Resultsmentioning

confidence: 99%

Glucosyl‐1,2,3‐triazoles derived from eugenol and analogues: Synthesis, anti‐Candida activity, and molecular modeling studies in CYP‐51

et al. 2021

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Synthesis, chemical characterization and antimicrobial activity of new acylhydrazones derived from carbohydrates

Cited by 16 publications

References 19 publications

Evaluation of antiplasmodial activity in silico and in vitro of N-acylhydrazone derivatives

Evaluation of antiplasmodial activity in silico and in vitro of N-acylhydrazone derivatives

SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents

Glucosyl‐1,2,3‐triazoles derived from eugenol and analogues: Synthesis, anti‐Candida activity, and molecular modeling studies in CYP‐51

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