Synthesis, antimicrobial and cytotoxic activities of 5-benzylidene-2-[(pyridine-4-ylmethylene)hydrazono]-thiazolidin-4-one and 2-[(pyridine-4-ylmethylene) hydrazono]-thiazolidin-4-one derivatives

Feitoza, Danniel Delmondes; Alves, A. J.; Lima, José Gildo de; Araújo, Magali J.; Rodrigues, Desterro; Silva, Teresinha Gonçalves; Góes, Alexandre José da Silva

doi:10.1590/s0100-40422012000400007

Cited by 9 publications

(3 citation statements)

References 16 publications

(19 reference statements)

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“…1), namely 3-PCPTC and 4-PCPTC, were synthesized in the laboratory according to the published method. 31 All the chemicals used in our research were of analytical grade and were used without any purication. 3-Pyridine formaldehyde (3 mmol) or 4-pyridine formaldehyde (3 mmol) was dissolved in ethanol (10 mL), and the solution was then added dropwise into a mixed aqueous solution of thiosemicarbazide (3 mmol) and acetic acid (catalytic, a few drops).…”

Section: Synthesis Of Inhibitorsmentioning

confidence: 99%

Inhibition of mild steel corrosion in hydrochloric acid using two novel pyridine Schiff base derivatives: a comparative study of experimental and theoretical results

et al. 2017

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Section: Synthesis Of Inhibitorsmentioning

confidence: 99%

Inhibition of mild steel corrosion in hydrochloric acid using two novel pyridine Schiff base derivatives: a comparative study of experimental and theoretical results

et al. 2017

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“…In a previous work of our group, new TSC compounds were synthesized and showed cytotoxicity against the cell lines tested [6,7]. Continuing this work, we purpose new modifications expecting to find new active compounds.…”

Section: Introductionmentioning

confidence: 97%

Synthesis of New Thiosemicarbazone Derivatives Substituted with Heterocycles with Potential Antitumor Activity

Barbosa

Souza

Rodrigues

et al. 2018

AJACR

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Aims: To find new thiosemicarbazone derivatives with antitumor activity and good physico-chemical parameters. Study Design: A preliminary SAR study with pyrrolidinyl, piperidinyl, and morpholinyl heterocycles as well as hydrogen, alkyl and phenyl groups in the thiosemicarbazone scaffold. Place and Duration of Study: Department of Pharmaceutical Sciences and Department of Antibiotics, from Federal University of Pernambuco (Brazil), between January 2016 and February 2017. Methodology: The thiosemicarbazones were synthesized through a condensation reaction between benzaldehyde substituted with heterocycles and several thiosemicarbazides, using a catalytic amount of hydrochloric acid. The new compounds were characterised using classical spectroscopic and spectrometric techniques. The cytotoxicity were evaluated using MTT assay against five cancer cell lines and doxorubicin as reference compound. The LogP was also predicted using the software MarvinSketch 17.4.3 and promising results were found. Results: We found five new thiosemicarbazone derivatives with excellent cytotoxicity. Conclusion: Thiosemicarbazone derivatives are promising compounds in medicinal chemistry field and certainly should be considered as scaffold for drug candidates.

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“…Therefore, for the synthesis of new 1,3,4-thiadiazolines and thaiazolidinone derivatives, there are several methods to obtain 1,3,4-thiadiazoles, mostly achieved by condensation substituted thiohydrazide with thiocyanate, also by the reaction between thiosemicarbazone with acetic anhydride [25][26][27][28][29]. The heterocyclic thaiazolidinone is mostly achieved by the reaction from the reaction isomethan group with thioglycolic acid [30], also a reaction chloroacetic acid with thiosemicarbazones [31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Anticancer, Antioxidant Activities and Molecular Docking Study of Thiazolidine -4-one and Thiadiazol Derivatives

Alsalim

Nasir

El‐Arabey

et al. 2022

Preprint

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Liver cancer accounts for a major portion of the global cancer burden. In many nations, the prevalence of this condition has risen in recent decades. New series of thaiazolidinones and thaiadiazolidine have been designed, synthesized, and evaluated for potential antioxidant and antihepatocarcinogenic activity. The antioxidant activity of synthesized compounds was evaluated using a DPPH assay. Furthermore, we examined the compounds against HepG2 cells using MTT assay, flow cytometry analysis through the cell cycle, reactive oxygen species, and apoptosis. The result showed that compound 6b has the highest antioxidant activity with IC50 =60.614±0.739 µM. The anticancer activity showed that compounds 5 and 6b have significant toxicity against liver cancer cells HepG2, IC50 values (9.082 and 4.712) µM, respectively. Flow cytometry experiments revealed that compound 5 arrested HepG2 cells in the S process, while compound 6b arrested HepG2 cells in the G1. Compound 6b had a greater reduction in reactive oxygen species and late apoptosis than compound 5. Substantially, compound 5 had affinity energies of -7.6 and -8.5 for Akt and CDK4 proteins, respectively, but compound 6b had affinity energies of -7.8 and -10.1 for Akt1 and CDK4 proteins, respectively. Consequently, compound 6b had lower binding energies than compound 5. In this work, we used multiple bioinformatics methods to shed light on the prospective therapeutic use of these series as novel candidates to target immune cells in the tumor microenvironment of hepatocellular carcinomas such as CD8+ T cells, endothelial cells, and hematopoietic stem cells. The results of antioxidant, anticancer, molecular docking studies, and bioinformatic analysis showed that compound 6b has a potential impact and could be developed for drug discovery with further research.

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Synthesis, antimicrobial and cytotoxic activities of 5-benzylidene-2-[(pyridine-4-ylmethylene)hydrazono]-thiazolidin-4-one and 2-[(pyridine-4-ylmethylene) hydrazono]-thiazolidin-4-one derivatives

Cited by 9 publications

References 16 publications

Inhibition of mild steel corrosion in hydrochloric acid using two novel pyridine Schiff base derivatives: a comparative study of experimental and theoretical results

Inhibition of mild steel corrosion in hydrochloric acid using two novel pyridine Schiff base derivatives: a comparative study of experimental and theoretical results

Synthesis of New Thiosemicarbazone Derivatives Substituted with Heterocycles with Potential Antitumor Activity

Anticancer, Antioxidant Activities and Molecular Docking Study of Thiazolidine -4-one and Thiadiazol Derivatives

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